How I Got Hired in Product with Amy O'Callaghan

Ever wondered how to step into the world of Product Management? Curious about what it takes to succeed and move up the ladder?

In today’s episode our guest host, Becca Moran, speaks with Amy O’Callaghan about how she stepped into a career in Product.

They cover:

• How she transitioned from a marketing role into product management.
• Practical steps for others who want to navigate into the product space.
• Advice on how to use informational interviews to figure out whether a specific product role (or company) is the right fit.
• How she’s moved up in her career and succeeded in senior level roles (plus tips on how you can do the same!)
• And much more!

About today’s host: With 5+ years of experience leading startup product teams and almost 10 years in the DC tech scene, Becca offers a wealth of valuable insights. She is currently the Vice President, Product & Engagement at Procurated, where she leads the product, design, and engineering functions for the company.

About today’s guest: Amy O’Callaghan is a product veteran with over 10 years of experience. She started in product at snagajob. From there, she worked for Launch Media, CarMax, and was most recently the VP of Product at Vangst, a talent marketplace for the regulated Cannabis industry.

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Becca Moran: I'm Becca, and

this is How I Got Hired.

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How I Got Hired is a series of interviews

where product managers share how they

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landed great product roles from PMs

who made a career pivot into tech

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to those with more formal training.

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How I Got Hired captures the various ways

to open doors into the world of product.

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We'll be talking about each guest's

recipe for success, what motivated them

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to get into product, how they prepared

for the interview, and what they

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Amy O'Callaghan: did to

set themselves apart.

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Becca Moran: Today, my

guest is Amy Hoek Callaghan.

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Amy is a product veteran with

over 10 years of experience.

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Amy started in product at Snagajob,

who we'll talk about today, then

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worked for Launch Media, CarMax,

and was most recently VP of product

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Amy O'Callaghan: at Vanks.

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Becca Moran: A talent marketplace

for the regulated cannabis industry.

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Amy, welcome to the

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Amy O'Callaghan: show.

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Thank you so much for having me, Becca.

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I'm really excited to get

to talk with you today.

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Becca Moran: I'm excited too.

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Um, so for listeners, um,

Amy and I have not had the

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opportunity to work together yet.

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Hopefully maybe one day in the future.

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Um, but we were introduced by

my boss a few years ago, and

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I've always really admired, uh,

the work that you've done, Amy.

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Um, thought that others would enjoy

hearing about your unique product

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journey and, and learning from you.

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So excited to get into it.

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Um, okay.

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So I thought of a fun way to get started

just to give a little bit of a color to,

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to who you are, uh, and continue to share

fun or embarrassing facts about myself.

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would be to do a little bit

of two truths and a lie.

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So, um, I can, I can

kick us off, uh, with my

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Amy O'Callaghan: list this time.

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I'm exceptionally bad at telling when

people are lying, so this is always

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great for the person playing with me.

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Becca Moran: I, um, I'm, I'm

not sure I'm a good liar, but I

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really, I probably put way too much

thought into what these should be.

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You're a great

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Amy O'Callaghan: strategist.

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Yes.

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I, exactly.

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Becca Moran: Um, and, uh, yeah,

so I, there's a theme to these.

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Um, okay.

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So number one, I have won multiple first

place ribbons for showing dairy goats.

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Amy O'Callaghan: Number

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Becca Moran: two, I have ridden a

horse around the grounds of Versailles.

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And number three, I grew up on

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Amy O'Callaghan: a 200 acre farm.

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Hmm.

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I'm gonna say, uh, you have not ridden a

horse around the grounds of Versailles.

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You would be wrong.

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Becca Moran: So cool!

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Um, that was an incredible

experience, uh, totally random, just

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like found this thing online and,

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Amy O'Callaghan: um, The reason

I picked that one because I was

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like, that's a historic property.

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There's no way they're letting

tourists clip clop around.

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But I found

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Becca Moran: somebody on TripAdvisor

that, um, does these tours and, um,

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it was an incredible experience.

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But, uh, the, the lie is maybe the most.

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You would think as someone who rides

horses and shown dairy goats that I

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would have grown up on a farm and in

fact, I grew up all over the place,

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but mostly in like suburban New Jersey.

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So,

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Amy O'Callaghan: oh, my goodness.

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I have a great fondness for goats.

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I have never shown them, uh, won

any ribbons on their account.

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Uh, but one of the developers in

my last company had a farm that he

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was working from and he had a live

goat cam going in our slack channel.

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So anytime you just needed like a pick

me up, you could hit the goat cam.

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It's amazing.

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They're so

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Becca Moran: sweet and

so fun and what's not

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Amy O'Callaghan: to love.

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So, all right.

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All right.

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I, I think mine, there is

significantly less detail though.

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Um, So, all of these are things I am

claiming that I have done one time.

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Skydiving, mountain

climbing, motorcycling.

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Ooh,

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Becca Moran: I'm gonna say motorcycling?

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Amy O'Callaghan: That is the lie.

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Cause I used to motorcycle

way more than once.

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I don't know if

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Becca Moran: that was

what I was thinking, but

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Amy O'Callaghan: yeah, the

original I was going to do is I

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have an intense fear of heights.

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I have climbed a mountain

and I've been skydiving.

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And I'm like, no, those are all true.

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I can't do that.

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I've got a lion.

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What's a cool way to lie and

make myself sound cooler.

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But yeah, no, actually I went through

a motorcycling phase up for kids.

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And now the gear is actually directly

above my head in the attic because

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I spent months finding women's

riding gear that was neither pink

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nor glittery, nor in blinds with,

you know, hearts or butterflies.

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So that's the one thing I sold the bike.

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Do you still have a bike?

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Okay.

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I don't know for right

now, I'm like, all right.

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The plan, because I too am strateging, uh,

strategering, is that, uh, when my kids

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get to the age where they think everything

I do is lame, I'll bring a bike back in,

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and then either they'll think motorcycles

are lame, which is a great win for me as

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their parents, or they'll think I'm cool.

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Like, one of those two

things has to become true.

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And either one of them is great for me.

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Yes,

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Becca Moran: um, my mom actually used to

ride motorcycles, um, broke both of her

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legs, thankfully not at the same time.

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Um, although I don't know

how much does that matter.

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Um, yeah,

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Amy O'Callaghan: yeah,

it was a, you know what?

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It was a risk assessment.

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It was a basic risk assessment.

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I was like, all right, uh, you know,

if I'm out of commission, these

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kids are going to be in a pickle,

so I can at least wait, you know,

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20, 25 years to get back on, I

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Becca Moran: think my mother made

the same kind of calculation.

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So, uh, thank you on behalf

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Amy O'Callaghan: of your children.

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Absolutely.

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Becca Moran: Well, awesome.

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Um, so let's get into it.

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I think, um, a great place

to start is at the beginning.

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So, um, And I think the story we

want to talk about today really is

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how you got into your first product

role, which I think is super cool.

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And there's so many different

ways, um, to get into product.

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And I love hearing

people's different stories.

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So.

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Maybe we can just kind of start

there and start with, um, you

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know, what did, what did your

early, very early career look like?

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What were you doing right before

you ended up transitioning into a

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Amy O'Callaghan: product role?

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Yeah.

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Um, that's a great question, especially,

I think it's been fascinating to

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watch how The types of beginnings

people have in a product career

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have shifted over the years, right?

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Because when I got into product,

there was no product level

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training at college or university.

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Those things didn't exist, right?

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Like the only way in was really

to kind of get adopted by an

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organization that was doing it.

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Um, I, uh, speaking of college and

university, I went to school for, uh, a

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very practical bachelor of fine arts in

animation because I was convinced I was

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going to go be a video game animator.

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Um, but it's

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Becca Moran: interesting because I was

looking at your LinkedIn and I literally

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had to Google what is it called?

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Kinetic kinetic

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Amy O'Callaghan: imaging.

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Yeah.

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Well, that's because I went to an art

school and they wanted the fanciest

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way possible to say animation.

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Um, yeah, I rarely

actually put my major on.

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I'm like, I just have a BFA.

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Don't worry about it.

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Um, yeah, so I had an internship

though while I was in school

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and that was in web design.

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Um, so when I graduated, I

actually stayed in a small web

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design firm for a little while.

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It wasn't a lot of mobility though.

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It was a great opportunity to kind of

learn everything, touch everything,

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do some basic front end coding, get

some account management under my arms.

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Um, eventually I wanted to

move on to a bigger place.

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So after six years there, um, I

transitioned to snag a job, which was

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my first real like corporate experience.

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Um, they were a good midsize

startup at that point.

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Um, I think I was higher number 256.

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So, you know, good midsize company,

um, lots of good practice in place.

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And they were one of the first

organizations in Richmond, especially

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to be doing product management.

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Um, I joined as, um, somebody who was

working in their marketing department.

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And as I got kind of my hands into

the business, like understood from my

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little vantage point where the problems

were, I eventually worked my way into

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being, um, social media manager there.

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And social media management is great.

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Because it is basically one long user

interview all day long, uh, often with

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the extremes of your user base, right?

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You're getting the people who are

really happy and you're getting

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the people who are really mad.

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And they're all talking about it

real time on Twitter or Facebook or,

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you know, today Instagram, but it

was, it was wild, but it was great.

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It was the perfect kind of immersion.

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And just hearing the problems and the

successes over and over and over again.

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Um, and so I.

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I would not have had the language to

phrase it this way, but what happened

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was I just started hearing the problems

that I was kind of fixing one off one

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at a time, doing my best to solve the

problem for each individual user, and I

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sort of followed those problems upstream

into the product experience where they

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were happening and tried to figure out.

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Well, what change could we make that

would solve this problem and prevent

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it from ever hitting social media?

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Right?

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And I would put together absolutely

gorgeous mock ups in a program

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called MS Paint that hopefully no

one actually knows about anymore.

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And, um, send them along with my idea

and proposal by email over to our

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team of product managers who I had

met on my first, like, building tour.

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And I was like, Oh my God, the

cool people are over there.

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Um, and I would just

email them all my ideas.

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Um, and eventually I sent

exactly enough emails and I

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don't know what the number is.

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Otherwise I would share that.

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I wouldn't gate keep

that kind of knowledge.

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Um, but they were like, Hey, we should

just train her to be an associate PM.

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Um, and so like, there wasn't

even really a rec open.

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Um, it was really just kind of

putting myself in a place where I

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was consistently demonstrating the,

um, the affinity and the skills of an

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associate PM and making that knowledge.

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Open to the product team, right?

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Like I know a lot of incredible

people who I think could make great

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product managers who are kind of

doing that in their own space, but

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it never reaches the product team.

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And so we don't know to reach out like the

claw and drag them into product and make

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them one of us like weird tech zombies.

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Um, but I think that was the thing that

helped was that I was doing that work,

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but then I was sharing it with them.

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And so they had visibility into

what I was doing and thought that

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it was a good opportunity for me.

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Um, so there was some conversations

between the head of product and the

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head of marketing and they kind of

did a little work around like how we

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were going to make that transition.

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Um, but ultimately that was a

really, really seamless one for me.

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That's super interesting.

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Becca Moran: And I, I love the

way that you described that as

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kind of like going upstream.

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I think that's really at the

heart of like kind of what makes

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someone a product person, right?

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That you're like, okay, I'm, I'm

not satisfied just kind of treating

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the symptom of this problem.

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Like I want to go to.

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The heart of it and, and stop it

at the source, uh, prevent it.

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And I think that kind of just taking

that initiative and being proactive

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and, and yeah, like I was, uh, saying

with another guest about how the

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product doesn't have a swim lane, right?

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You just kind of have the whole pool.

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And I think that's kind of it, right?

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Is like, you didn't look at

that role and say, Oh, I'm

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just the social media manager.

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I just, you know, You're these things

and try to, you know, make people happy.

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Like you said, Hey, I

don't have a swim lane.

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I'm going to go that step further and

figure out like, how do we prevent

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more people from running into these

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Amy O'Callaghan: same

issues in the future?

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So I do think I was, I was cautious of

not stepping on too many toes though,

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which I'm grateful to my time in

marketing, because I think it actually

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did a good job of teaching me like.

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How to talk about a success in such a

way that you look great, but more it's

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about talking about the team, right?

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You're not talking

about how great you are.

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You're talking about

how great the work was.

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Like it was a very good, like

small public relations bootcamp of

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like, and I've used that for every

product team and every product org

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I've been a part of since then.

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Cause I've definitely had people

that were like so hungry for the

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role that they were like constantly

just like founding a product team.

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Like, Hey, look what I did.

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Look what I want.

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Like, here's what I am.

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And I think there's a fine line, right?

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And I probably stepped over or towed

the line a couple times in ignorance.

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But, but yeah, it was ultimately

just coming from a place

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of, I wanted to fix stuff.

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Like when people ask why I got

into product, it's like, cause it's

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just solving problems at scale.

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And that's so delightful to do.

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Yeah.

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Becca Moran: And what

was that role like this?

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So you were hired into was it an

associate product manager role initially?

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Yeah.

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I'd love to hear more about like,

what that role actually involved

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and how you actually kind of.

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Started to dip your

toes into actual product

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Amy O'Callaghan:

responsibilities for sure.

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Yeah.

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And Snagajob actually

did a really nice job.

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It's one of several orgs I've

been fortunate to be in where

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they created a really intentional

pathway into product, um, both for

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external and for internal talent.

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Um, and so what happened when

I moved into product and that

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associate role was, you know, got

invited to all the product meetings.

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It wasn't a huge product team.

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I think it was about like

eight to 10 people at the time.

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Um, we, they pretty quickly, uh, put

us all on a plane and send us out to

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Marty Kagan's weekend workshop, which I

was like, this is the best thing ever.

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Um, I don't know that there's any

better way to start your product career

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than like sitting in a room, listening

to Marty Kagan talk about eBay.

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Um, and, uh, so really they, they,

they carefully positioned me so

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that I could form relationships

with other product managers and

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like build mentors within the group.

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They also put me in a space.

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Where the harm I could do was very

limited and the ability to learn was

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extremely high and granted, I still

managed to do some dumb stuff, but, um,

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I think that's really important, right?

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The first job that they positioned

me for was helping our customer

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and member support agents.

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Um, understand like where they could

gain efficiencies and taking the bugs

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and issues that they were hearing.

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It was a larger role of what I was already

doing as a social media person, right?

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I was like just opening the

floodgates from social media to

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and everyone who talks to an angry

customer or user all day long, right?

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And synthesizing that information across

escalating the important stuff that I

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couldn't handle up to the rest of the

product group managing what I could on

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site and finding ways to close gaps.

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So one of the very first things

I did was identify that, um, all

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of our support agents kind of had

to roll their own support scripts

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every time a question came in.

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So we put in place a single unified like

four set of support scripts and made

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them accessible to everybody so that

everyone wasn't trying to constantly a

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You know, reinvent the wheel, which was

great because from a branding perspective,

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it gave snag a job a lot more control

from a customer service perspective.

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It gave people more time and energy back

to actually answer calls rather than

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kind of doing copywriting on the fly.

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And at the end of the day, it results

in a more reliable customer experience,

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because now you don't have like.

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15 to 20 different people making

15 to 20 different ways to

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respond to a single incident.

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Um, so it, I think it was great because

oftentimes I see organizations start

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associate PMs in places that they

can really get themselves in trouble.

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You know, the business has a ton of

urgency there, you know, there was an

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opening because they needed somebody.

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I think customer support is an

amazing place to start somebody out.

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There's several of those like little

safe havens around an org where

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you can almost always use the help.

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And the amount of damage somebody can do

is kind of a little bit insulated from

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the rest of the org, like they're not

going to bring down the OKRs for this

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quarter from the member support side.

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Becca Moran: Yeah, that actually,

um, kind of gets a little bit

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to a question that came to mind.

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Like, did you ever find in that role that

you, like, was that frustrating at all?

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Did you find that you were like

in conflict potentially from maybe

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more or with like the bigger top

down organizational priorities?

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Cause it's, I'm thinking about like my

experience, um, working and like trying

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to prioritize those types of ideas, things

that come from your customers that, you

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know, there can be a lot of noise, right?

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Like you don't want to jump at every

single issue that a customer brings up.

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But at the same time, like, If you can cut

through that noise and you can see things

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kind of thematically, you can actually

identify some changes that can be equally

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as consequential, I think, as some of

these more top down driven initiatives.

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So I'm just curious, like.

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Is that something you ran into?

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And like, how did, if so,

how did you handle it?

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Amy O'Callaghan: Yeah, I, I think

everyone in product probably

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runs into that all the time.

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Um, or I'm just a very, uh, contrary

person who's constantly just asking.

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People to prove to me why the things

we've prioritized are the way they are.

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But, um, I think you actually described

it really perfectly, which is the, the

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layer that was missing, because obviously

there was a ticketing plate, like in

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place, there was, uh, you know, uh, SLAs

in place, response times, all of that

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jazz, all those things already existed.

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What I really was able to do in that role

was to synthesize the things that were

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these individual floating bugs and say.

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Here's why all those things

are happening, right?

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Like and make it easier for a product team

upstream to take the work and say, like,

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Oh, we see what the benefit of solving

this would be, and they've already done

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the investigative work, so it's much

easier for us to pick up and do our Q.

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A.

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Isn't going to spend like two

days this week, you know, looking

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into this and trying to figure out

how all these bugs are connected.

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Um, and the other thing is, I

think that this was part of where

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I started to leverage the work.

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Discovery to help make sure that the

things that I truly felt were important

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were given consideration, even if

they weren't ultimately prioritized

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because I never want something.

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To get prioritized that shouldn't be

right, like, no matter how passionate

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I am about it, if they're literally

working on something more important

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than I should be waiting my turn, so I

love to make sure I put it forward and

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I make sure there's shared understanding

between me and that other team about

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here's the actual customer impact, right?

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Like, let me let you listen

to the customer call from one

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of the 60 people that talk to

customer support about this today.

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And here's the percentage

of customer support time

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currently going to this issue.

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Thank you.

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And here's like, you know, just kind

of putting the whole opportunity

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assessment, um, together for the team

and just making it more consumable.

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Because I think so often, I don't know

about you, but in the times when I've

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been on the incoming side of a stream

of bug tickets, just the sheer work of

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sitting down and Sherlocking which ones

go together and solving the jigsaw.

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Can sometimes prevent you from

picking up those tickets and

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moving them across the board.

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So I was kind of solving

like half the puzzle before I

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asked anybody to take a look.

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I love that.

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Becca Moran: I'm thinking a

little bit more about kind of this

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associate product manager role.

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Um, would you say that, you know,

for anyone who might be interested

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in getting into product and

looking for those types of roles?

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Um, like, you know, aside just

from kind of like searching for

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that title, like what types of

companies do you think should have

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associate product manager roles?

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Like, I, I think that and, and if

you have any thoughts on maybe what

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prevents more companies from having

that kind of position, but it strikes

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me that maybe Snagajob was at a certain

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Amy O'Callaghan: scale that could

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Becca Moran: support that.

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Like thinking about my experience working

very small, early stage startups, like.

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I know like we're not in a position

today to have that kind of role,

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although hopefully at some point

we can kind of support that.

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And I think it's incredible

in terms of like giving people

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career paths and everything.

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Um, but yeah, what's, what's

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Amy O'Callaghan: your

take on kind of that role?

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Becca Moran: Who, who is doing it right?

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Who should be doing having

that position that doesn't?

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Um, yeah.

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Yeah.

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Amy O'Callaghan: I mean, I think

to your point about why more

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companies don't have this role.

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I think it's because people

hire product managers when they

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have a problem to solve, right?

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And the only companies that I see

proactively putting product learning

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agendas in place and associate

product management, um, tracks in

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place are those that are concerned

about home growing their talent.

428

And having a bench of people to fill roles

and solve problems when they come to them.

429

And that does take a

certain amount of capacity.

430

It takes time away from

your more senior people.

431

Like there's a whole slew of things that

have to happen for an associate product

432

manager to actually get good experience.

433

Um, speaking a little bit to the

size, I think it depends, right?

434

Like my last product

organization was pretty compact.

435

You're about 25, including engineering.

436

And.

437

I looked around the org and very early

saw somebody and was like, I think

438

they might be a great product manager.

439

Like I think they've got the stuff.

440

I came into the org and discovered

they were like personally holding up

441

like six manual processes that were

keeping things running and like never

442

taking vacation and just like solving

all the problems as they came up.

443

And I was like, yeah.

444

Um, That's it.

445

And so, I mean, what we fundamentally

did there, you know, I talked to

446

them about it and just sort of, you

know, talk to them a little bit about

447

what product was, what it is as a

career and kind of the opportunities

448

that having that experience unlocks.

449

And talked about the rest

of their career aspirations.

450

Like what were they thinking about?

451

What were they interested in?

452

And at the end of the day, I was

like, look, I don't know that

453

your day to day will change a ton

because you're still going to be

454

accountable for some of these things.

455

But I think we could work

together and get some of these

456

processes to be more efficient.

457

You know, get them into a

place where you don't need a

458

human in the loop all the time.

459

That's a business resilience thing

that I could talk about for ages.

460

But, um, and at the end of the day, what

we ended up doing was moving them into

461

an associate product manager role, and

they were still triaging bugs and doing

462

customer support and all those things.

463

Um, but on the other hand, they were

coming to the product team meetings and

464

we were taking the bug tickets and we

were making sure that we were following

465

a rigorous prioritization process and

like they owned that process and they

466

were making the tickets for the bug.

467

So it was a very early primer and like.

468

You know, baby steps

into product management.

469

Um, I definitely wasn't able to send them

to Marty Kagan and, you know, there was

470

a, a limited pool of product people to

hang out and become, uh, in a mentorship

471

relationship with, but to your point

about just making opportunities for

472

people, I am constantly blown away that

I get to do this job that somehow like.

473

I got I got lucky enough to be in it.

474

And so I'm always looking for

ways to pull people in because I

475

don't know about you, but I just

I see product people everywhere.

476

Like, I see someone solving

a problem and I'm like,

477

Becca Moran: yeah, that's that's

478

Amy O'Callaghan: the DNA.

479

Um,

480

Becca Moran: for those that might

be listening to this and are

481

maybe not in a, like, product

482

Amy O'Callaghan: adjacent

483

Becca Moran: role.

484

So, like.

485

Thinking about what you were

describing, this kind of exposure that

486

you had in the social media role, I

487

Amy O'Callaghan: think, to your

point, customer support is a

488

Becca Moran: great one where, like,

there is a very natural kind of

489

Amy O'Callaghan: overlap, but, like,

490

Becca Moran: what if you're working for a

part of the company that there's less of

491

that or less maybe opportunity to interact

with someone from the product team where

492

you just may not have that exposure.

493

Any thoughts on how someone in a role

like that might be able to, what, what

494

they could do to maybe, um, like start

to get more of that exposure and build

495

certain skills that could help them be a

496

Amy O'Callaghan: good candidate for sure.

497

And I think this applies not only to

people who are in an organization that

498

has product, but they're removed from it.

499

Um, but also to people who

are not in product at all.

500

I was speaking recently, um, to a class.

501

Of people that were, um.

502

In product, uh, master's work over at

VCU and there were people from, you know,

503

Richmond public schools in the room and

I'm like, you guys are solving problems

504

all day scrappily with no resources.

505

Like you can turn that into a case

study and I think it's a combination

506

of having again that raw ingredient.

507

If I want to solve the problem, I'm not

going to like, let resource constraints.

508

Keep me from doing it.

509

I'm not going to fall in love

with the first thing I think of.

510

I'm going to look for the right

solutions or the best solutions

511

instead of getting laser focused on, on

whatever's the most interesting solution.

512

And then you pair it with the

language and the understanding

513

and how you talk about it, right?

514

Because I think you and I probably have

met a lot of people that solved a lot

515

of cool problems in a lot of ways, but

they would not describe it in a way that

516

speaks to the product management lexicon.

517

And I think for the people that are

really interested in pursuing this as a

518

career, identifying where you're solving

those problems and how you're doing

519

it in a product way and being able to

speak the language is really important.

520

And like the master's programs

that are popping up, like.

521

Our local university does a

master's in product innovation now.

522

And I'm like, dang, I went to this

school and you guys wouldn't have

523

known what I was talking about

if I asked for this as a major.

524

Um, and like there's a whole class

of people coming out of schools

525

now that are classically trained

in this and that's awesome.

526

But I also still have a major soft spot

for the rogues that are like sneaking

527

in like we did around the edges.

528

Um, and I think it's that

combination of like problem solving.

529

And being able to speak to it that way.

530

And I mean, one of the strongest product

people I know, she was actually at

531

Snagajob when I was in, um, the marketing

department and she was an events planner.

532

She planned all of our

major corporate events.

533

She like did all of our, you know,

conventions and managed when we

534

went to the national restaurant

association to sell software.

535

And she was amazing at that.

536

She had a ton of energy, was outgoing,

um, excellent organizational skills,

537

was able to rally everybody, sometimes

literally get them on the bus and

538

get them where they were going.

539

And you see all of that

in her product, right?

540

And that was, that was, I think, part

of what got her in, you know, I, I don't

541

actually know the specifics of how she

transverse going from events to product,

542

but she did it inside snag a job.

543

And I would.

544

I would argue that you can see a

direct line between the amazing

545

events manager and the incredible

product person she is today.

546

Yeah,

547

Becca Moran: yeah, I, I think

it's such a great point about

548

kind of the lexicon of product.

549

And I recall a few years back having

a conversation with someone who

550

similarly wasn't in a product role was

looking to kind of make that shift.

551

And I had worked with them and I

knew that they would be good at it.

552

And my advice to them was like,

you just need to learn how to

553

talk like a product person talks.

554

And, um, Like, to be able to do

that super fluently takes time.

555

But I think to be able to do it well

enough to go into an interview and

556

just, like, frame your experience

in a certain way, ask questions in a

557

certain way, um, like, think through

a problem in a certain way, I don't

558

think that's actually that hard to,

like, build some of those fundamentals.

559

Um, and I think it that can be, um,

a huge way, I think, to, like, level

560

up going into an initial product

interview where I think a lot of hiring

561

managers, you know, if you haven't had

the opportunity to be exposed to that

562

person, you know, they're not like an

internal candidate that maybe you've seen

563

Amy O'Callaghan: some of these.

564

In a traits, um,

565

Becca Moran: if you're just kind of

interviewing an external candidate,

566

that's trying to make that pivot.

567

A lot of hiring managers are going

to kind of screen out people that

568

can't really talk through some

of those fundamental product.

569

Concepts or or ways of thinking and so.

570

I think it's a really great point that,

like, if you're the kind of person

571

that feels like you have some of those

innate abilities and characteristics

572

that we're describing, and you're not

sure kind of how to break through, I

573

think building that lexicon of, like.

574

How do I talk like a product

person is a really great way to

575

Amy O'Callaghan: think about it.

576

Yeah.

577

I usually advise people.

578

I'm like, look at a problem that

you're trying to solve today.

579

Does not have to be a tech problem, right?

580

That's the great thing about product.

581

We're everywhere solving

everything doesn't matter.

582

And, you know, put together your

personas, do a journey map, you know,

583

put together, uh, uh, opportunity

solutions tree and pick, you know,

584

some things to run tests on and do an

opportunity analysis and a risk analysis

585

and like, just practice these things.

586

Um, to your point, it's

like gaining fluency, right?

587

And you're going to be so

awkward at it the first time.

588

And the fifth time that you do

it, you know, you're going to,

589

you're going to be a lot better.

590

Um, but for sure.

591

And the other thing, and I think

this makes product hard too, is

592

every organization does product

a little different, right?

593

And so the lexicon that, you know,

Microsoft wants and the lexicon that

594

the Amazon hiring manager are looking

for probably a little different.

595

So I always try to advise people to

at least do enough networking to have

596

one conversation with somebody from

product or engineering or design in

597

the org that you're interested in.

598

One, just like make sure you

actually want to go over there.

599

Right.

600

Right.

601

And two, what do they care about?

602

Like what's the framework?

603

Like what are the things they do?

604

Are they running jobs to be done?

605

Like what?

606

What kind of words do you need

to be able to be fluent in?

607

Um, we can say it's the regional

accent of your company, right?

608

Like you walk in there and you don't,

you don't, you don't talk the same way

609

they do and they're going to kind of look

at you and be like, I don't know, but

610

you can get in there and talk, you know,

the lingo that they're comfortable with.

611

I think it, it gives you an advantage.

612

Yeah, I,

613

Becca Moran: I totally agree.

614

And I think the idea of like doing

informational interviews, um, is huge.

615

I, um, it makes me think a little

bit about when I took this role at

616

Procurated, um, I hadn't been actively

looking and, um, I, I was really excited

617

about the opportunity, but I had this

like kind of feeling that I was like,

618

oh, like I would have wanted to be much

more intentional about where I go next.

619

And I felt like, Oh, I, I should

have stopped and thought about,

620

like, what my next role would

look like and, and whatever.

621

And so I kind of, like, forced myself

to go and do some informational

622

interviews with people at other types

of companies really quickly to be like,

623

okay, I just want to kind of have a

point of comparison to make sure that

624

this is what I want to jump into.

625

Um, and I, I was entertaining the idea.

626

I thought for a minute I wanted to

work for, like, a digital agency.

627

Um, because I've worked with some,

um, shout out to the team at Vigit,

628

who I've worked with at a couple

organizations, and they're super talented,

629

and they do great work, and I've just

always thought, like, that would be

630

such a cool environment to work in,

and, um, you know, I would probably

631

learn so much from the people there.

632

Um, and I, I did an informational

interview with somebody just to kind

633

of explore that path a little bit and

ultimately concluded that I didn't

634

think that that environment would

necessarily be the right fit for me.

635

Um, and it can certainly be a

very intense type of product role.

636

Um, but

637

Amy O'Callaghan: yeah, I.

638

massive advocate of informational

interviews in like every aspect of life.

639

Um, yeah.

640

If it weren't for an informational

interview series, I wouldn't have known.

641

I didn't want to be an animator, right?

642

Like I was like, Oh, I

want to work at Pixar.

643

I want to work for blizzard.

644

And then I talked to a couple

of the other, like, no, you

645

work incredibly long hours.

646

And unless you're in a major gaming

studio, you get laid off at the end

647

of the project because they don't have

funding lined up for the next one.

648

And then you have to move

wherever the next job is.

649

And I'm like, Oh,

650

Becca Moran: okay.

651

Uh, this, this sounds,

652

Amy O'Callaghan: and you know, like.

653

Even I was in a, um, a coaching group,

uh, a little while ago, shout out to

654

my swell people and um, and we had a,

a member who was talking about like,

655

just not being sure about whether she

wanted to move to pursue an opportunity

656

or whether she wanted to stay where

she was and like pursue a promotion or

657

whether she wanted to do what or what.

658

And we were like, what do you

want your life to look like

659

in like 10, 15, 20 years?

660

Right?

661

Mm-hmm.

662

like, what do you imagine for yourself?

663

And she actually had a very clear

end state she was going for,

664

and I'm like, Well, one, I think

that clarifies some of the things

665

you're currently stressed about.

666

Like, I wouldn't worry about scenario

A, because it has nothing to do with

667

the future state you think you want.

668

I would put yourself on the path, and

then I would go find some people that

669

are living that life that you want for

yourself in 20 years, and make sure

670

that the things that they have are

the things you actually want, right?

671

Because you would hate to do

all that work for 20 years.

672

It's a very product mindset.

673

Like, when you were talking about Doing

an informational interviews because

674

you were like, Oh, it's just so great.

675

But I don't want to just

jump on the first thing.

676

It's very much don't get

shiny object syndrome, right?

677

Exactly.

678

I love that your instinct when

presented with this amazing thing was

679

also like, I'm going to look around.

680

I'm going to make sure because you didn't

want to make like a binary decision.

681

And that's amazing.

682

Yeah.

683

Becca Moran: Well, and it's funny

because I think, you know, we're talking

684

about this product lexicon and a way

of thinking like a product person.

685

And I think Once you start doing it, you

kind of can't stop or if you, you always

686

have kind of thought that way, but it's

something we talk a lot about, um, within

687

procurated, like, how can we approach.

688

Every problem, problem the same way

we've approached product problems, right.

689

And like apply product thinking to lots

of different things, like how, like

690

company culture or whatever, right.

691

Things that maybe are not immediately

where you would think to apply that.

692

I once took

693

Amy O'Callaghan: a team's,

uh, retrofeedback for a

694

year and we were struggling.

695

We'd been pulled in a lot

of different directions.

696

Um, it was a great team, but they'd been

given too many different types of work.

697

And so we'd had to split

people up into like little

698

miniature teams inside the team.

699

And so like the culture in the

team was really fragmented and

700

like no fault of anybody's.

701

It was just how we were

surviving the workload.

702

And I took the retro

feedback from the year.

703

I sent, I put it into optimal sort

and I sent it out to the team and I

704

was like, if you have time, if you're

interested, I want you to do a card sort.

705

And I had them like affinity map the

cards together into themed groups

706

and then name them if they wanted

like do a classic digital card sort.

707

And then used that to create the bones

of an opportunity solution tree and

708

held like a retro roundup where, sorry,

this is my very small, great Dane.

709

Um, basically said, okay, here's

the things that are going well.

710

Here's the things that aren't going well.

711

Here's the themes, like, what

do we actually want to pursue?

712

And we got down to like branches of the

tree where we wanted to change outcomes.

713

And we started identifying.

714

Things we'd even tried

throughout the year.

715

We were like, okay,

this was an experiment.

716

We didn't talk about it this way, but this

was the thing we tried to fix a thing.

717

Do we like how it went or not?

718

Like, do we consider this a pass or fail?

719

And like, yeah, it's great to use

like product tools all over the place.

720

I can tell how much my, my friends

and loved ones like me at any given

721

moment is when I'm in a good place

with them, they think it's amazing.

722

And not otherwise they're like.

723

Why is business Amy at

Thanksgiving, you know, business

724

Becca Moran: Amy wasn't invited to this

conversation, but that's hilarious.

725

Um, I want to just touch kind of quickly

as we move to wrap up the episode.

726

Um, you know, I think we've talked a

lot about how you got into product and

727

I think that's an incredible experience.

728

You've also moved up and had incredible

success, um, in more senior roles.

729

Um, is there anything you want to

share about kind of that process?

730

If, if there's anyone listening, that's

maybe at a more advanced stage in their

731

career and is not looking at how to get

into product, but maybe instead how to,

732

to continue to move up into more senior

roles, um, just any thoughts from your

733

experience that you think would be helpful

for someone in that kind of position.

734

Absolutely.

735

Amy O'Callaghan: Um, I think a big

one and this is kind of just life

736

advice is self awareness, right?

737

Like, understand your strengths,

understand where you have opportunities

738

and sort of assess, right?

739

Like, is that an area where you

need to build competency where

740

you need to build strength?

741

Or is that an area?

742

Where you can actually succeed by

over indexing in another spot, right?

743

Like I personally, not the

strongest analytics person, right?

744

If you give me a math problem and you

need me to answer it right now on the

745

call, it will be an absolute disaster.

746

You'll really see that BFA shine.

747

Um, but in a lot of organizations,

I'm either afforded like an Excel

748

spreadsheet with which to do my

calculations or partnered with an analyst.

749

And so I've really leaned in to like

the discovery side, the storytelling

750

side, the empathy side as like my area.

751

But there are some incredible people

on like the business analytics side

752

of products that like, you know.

753

If we were both passionate about

something, we could talk each other under

754

a table on completely different terms.

755

And like, you know, the tide, the

leader who was tie breaking, um,

756

you know, and there's that same

deal on the tech PM side, right?

757

Like technical product management

is a whole nother thing.

758

So like really understanding what

gives you energy and like where

759

you're going to bring your special,

like verb to the, to the role and

760

investing there and growing yourself.

761

And the other thing, and this is something

I think I carry from my time in marketing.

762

I had an incredible leader in the

marketing organization at Snagajob.

763

It was Mike Ward, was a great guy, led

the team with empathy, but the other

764

thing he was really good at was always

making sure the rest of the organization

765

knew what the Marcom team was doing.

766

That was so great and why it

mattered to the rest of the org.

767

And so there is a, a piece of

our work that is making sure that

768

our team's value is understood.

769

You need to also be able to

do that for yourself, right?

770

Like, and oftentimes if you're making

sure the organization understands the

771

value of your team, they will see that

as a reflection upon you, but doing

772

great work in a vacuum in an organization

that's happy to just like, say, cool.

773

Thanks for doing the great work.

774

Keep doing great work.

775

It helps to have a little

bit of hype man, right?

776

Helps have a little bit of theater

kid in you and be able to write

777

like a really good internal press

release or be able to do a really

778

great shout out at the team meeting.

779

Um, because sometimes I see people doing

amazing work, but they don't elevate

780

it to the rest of the org in a way

that gets them the next opportunity.

781

And I think those things

are really important.

782

And then finally, like, Finding your

advocates, finding your mentors, turn

783

all of your great discovery abilities

on the leaders in your org and the

784

product people that are above you

in an organization or other orgs and

785

understand what they think it would

take for you to leave that gap, right?

786

Like, what are the

competencies you need to build?

787

Um, CarMax does a really good

job of actually putting people

788

through a structured program for

their associate product managers.

789

And also for their

leadership product roles.

790

Like when you move from, from competency

to competency and from level to level,

791

they do a really good job, um, giving

you the opportunity to invest there.

792

So there's companies that do

that, but they are, I would

793

say, less than, than the norm.

794

I'd say most of the time you're

going to be, you're going

795

to be doing it on your own.

796

And so making sure, again, you use

those product skills on your own career

797

and think about what you need to do

to make the next steps, because it's

798

going to be different for everybody,

but the tools you use to figure out

799

your pathway are kind of the same.

800

Becca Moran: Yeah.

801

I totally agree.

802

And I think in some ways it kind

of comes back a little bit to

803

where we started, like this.

804

I liked what you said about

really getting smart about how you

805

communicate and, um, share the great

work that you, your team are doing.

806

Um, and I do think that's a really

important part of Most product roles and

807

and using that same lens to think about

how you apply that in your career it

808

but also balancing, you know, it's not

like shameless self promotion, right?

809

In the same way that you were

talking about, um, there's a

810

nuance to you weren't just.

811

Bombarding the product team, you know,

when you were the social media manager

812

with like all of these, you know, you

weren't annoying the crap out of them.

813

I

814

Amy O'Callaghan: don't think so, but I

actually know one of the people that was

815

on that email distro and I'll ask him

just to see like, Hey, how bad was it?

816

Um, yeah, no, for sure.

817

And I think, I think you can always

put this in customer parlance, right?

818

Like if you wouldn't send an update

to a customer about it, because

819

it's not valuable enough, like, and

it might cause them to unsubscribe

820

from your email list, why would you

tell anyone in the company about it?

821

Right?

822

Like always put yourself in

that person's shoes and ask,

823

do they care about this news?

824

And if they don't care about the news,

is it because it genuinely doesn't matter

825

because they don't understand why they

should, in which case, like figure out how

826

to make that connection spark for them.

827

And if it doesn't matter to them

and you just wanted them to know,

828

then like leave them alone and

they'll listen harder next time.

829

Yeah.

830

And you know, I think at

831

Becca Moran: the core of that is.

832

Empathy, which in my mind is like the

number one trait that you must have if

833

you're going to work in product, right?

834

The ability to think about like,

what does this person want?

835

What do they care about?

836

Not just what do

837

Amy O'Callaghan: I want to tell them?

838

I definitely think I can see people that

do not have the empathy chops making

839

their way to a certain level in product.

840

But most of the time, at least

in an organization where you

841

really want to spend time, they

hit a ceiling at some point.

842

Where, you know, whether that's

before they're managing people or

843

something and they just sort of hit

that empathy wall and they either have

844

to, like, learn the empathy skill or

kind of just stay where they're at.

845

I think you're right.

846

Becca Moran: Um, all right.

847

So to wrap up our conversation, I have

a short list of my rapid fire questions.

848

So I'm just going to, uh, fire these at

you and and we'll turn through it quickly.

849

But okay.

850

So, um.

851

Do you think that a close friend or family

member could accurately describe what

852

Amy O'Callaghan: you do?

853

Um, it varies, and I know this

specifically because every Thanksgiving

854

I ask everyone at the table to

describe what they think my job

855

is, and the person who gets it

closest gets the first slice of pie.

856

Nice.

857

Yes.

858

Last year my partner

did a pretty good job.

859

They got real close.

860

They got first piece of the pies.

861

Yeah, my parents have no idea.

862

They think I make the internet.

863

My dad tried to give me a bug

report for Google once and I was

864

like, let me talk to you about what

happens when you submit this bug.

865

I can't control it, but let me

tell you what, what's about to

866

Becca Moran: happen.

867

Yeah, no, my, my parents have no idea.

868

And, and honestly, I think last time

the conversation came up, uh, one of

869

them thought that I still worked at

Xometry and I was like, I haven't worked

870

there in like almost five years guys.

871

Um, all right, what is one product or

tech like word or phrase, maybe something

872

from our aforementioned lexicon, uh, that

you wish you never had to hear again?

873

Amy O'Callaghan: If I hear us talk

about touching customers again, I'm

874

going to just climb under my desk and

hide there until the next ice age,

875

because it's creepy and it's weird.

876

And I don't know who started it, but we

need to all get together and stop it.

877

Yes.

878

Nobody should be touching anybody

if they're not expecting it.

879

I don't care what part of

the journey they're in.

880

This is a virtual world, you

881

Becca Moran: know, so.

882

It should be easier now than ever.

883

Um.

884

Yeah, plus one to that.

885

Um, how often, uh, maybe think

of in recent history, most

886

recent role, uh, how often do you

actually talk to your customers or

887

Amy O'Callaghan: users?

888

Um, most recently, um, I would go

unfortunate long desert like spans of time

889

not talking to anyone and then I would

kind of go on a discovery binge, right?

890

I would clear my calendar for two weeks

and I would just look back to back to

891

back to back to back to back to back.

892

Um, I typically like to shoot for

like five customers a week, right?

893

That's gonna give you a

nice diversity of opinions.

894

Um, you've got more than...

895

One persona, you might need to

think about how you split that up.

896

But like, I think that's a great way

to keep yourself from getting too

897

pinned into a single customer story.

898

Like our empathy is a superpower, but it

is also dangerous because we can get hyper

899

focused on fixing it for a single person.

900

And then we build something that is really

great for that guy over there, but doesn't

901

work for like the rest of the users.

902

So, um, Yeah, it really depends.

903

I'm all over the place.

904

My best weeks, I talk

to a lot of customers.

905

Yeah,

906

Becca Moran: I, I find the same.

907

I think it's very common to kind

of have these like ebbs and flows

908

with these customer conversations.

909

But like, I think the ideal everyone

strives for is like, how do we make that

910

a more consistent part of our process?

911

So, um, all right.

912

What book or person has been

most influential in your career?

913

Amy O'Callaghan: I'm going to say,

um, one of the leaders that I had

914

in my product time at Snagajob,

um, her name is Megan Overton.

915

She is a fantastic, she

actually just changed.

916

She was at Capital One for a long

time and she is now, um, moved

917

into a startup role, but the thing

that she did was she was always

918

incredibly transparent with her team.

919

Like I always felt like I could trust her.

920

Um, Like, even when the news

wasn't what I wanted it to be

921

or the feedback was challenging.

922

I always knew that like it was coming

from a place of genuinely wanting

923

me to do well and me to do better.

924

Um, and then finally, like she really

advocated for my team to have the

925

breathing room in the space to solve

problems rather than to chase specific

926

outcomes that leadership was pushing.

927

And it resulted in some of the

most absolutely magical practice.

928

Perfect years of my product career so far.

929

Um, and I have also seen not just for

me, but for other people, she has created

930

this incredible nest of product managers.

931

Um, and you just know if you're talking

to somebody that's worked under her that

932

you're about to have a great conversation.

933

That's amazing.

934

Becca Moran: Very cool to hear about

people that are doing so much good

935

for the product community in that way.

936

All right, last question.

937

When you were a kid,

what was your dream job?

938

Obviously you didn't

think you were going to be

939

Amy O'Callaghan: working in product.

940

Nobody knew what product management was.

941

So what did you think you'd be doing?

942

I was very specific.

943

I was very specific and I had three jobs.

944

I was going to be Batman.

945

It's going to be Indiana Jones,

and it's going to be Peter Pan.

946

Becca Moran: Just like rotating

in different days of the week.

947

Amy O'Callaghan: I really

hadn't thought it through.

948

I mean, particularly Batman and

Peter Pan, they're going to have

949

some hours overlap there, right?

950

Like they're both nocturnal.

951

Like Indiana Jones can get some stuff

done during the day, but I don't know.

952

I don't know.

953

Younger, it was very aspirational.

954

Clearly it likes a costume.

955

It sounds like

956

Becca Moran: you wanted to help people,

which, you know, that ties in, I think.

957

So I'm here for it.

958

And I think you could probably

still wear a costume to work

959

Amy O'Callaghan: if you want.

960

Oh, for sure.

961

Oh, I've dressed up as Indiana Jones for

multiple holidays, uh, for Halloween.

962

Like kind of my classic, like if I don't,

if I'm not part of a group, I'm going to

963

show up as a disturbingly accurate Indiana

Jones and that's just my call sign.

964

Becca Moran: Love that for you.

965

Amazing.

966

All right, well, we'll wrap up there.

967

Thank you so much.

968

I mean, this has been a

really fun conversation.

969

I know I learned a lot.

970

Um, a lot of really good kind of

reminders and great perspective.

971

So.

972

Thank you.

973

Thank you.

974

Always great chatting with you.

975

And, uh, yeah, thanks for being on the

976

Amy O'Callaghan: show.

977

Fantastic.

978

Thank you so much for the invite.

979

It was a great conversation and,

uh, grateful for the opportunity.

980

Tim Winkler: Calling all

startup technologists.

981

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982

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985

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987

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988

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989

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990

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991

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