In this episode of the CTO Compass podcast, Mark interviews Kelsey Daingerfield, founder of Pocket COO, who specializes in bridging the gap between technical teams and executive leadership. Kelsey shares her journey from higher education to entrepreneurship, discussing the importance of the visionary vs. integrator dynamic, the role of a fractional COO, and how to identify operational red flags. She emphasizes the significance of effective delegation, change management, and communication within teams, as well as the need to change the perception of IT departments. Kelsey also highlights the potential of AI in optimizing operations and shares a success story of transforming a business to achieve greater efficiency and work-life balance.

Chapters

00:00 Introduction & Background

02:13 Visionary vs. Integrator (Rocket Fuel)

05:00 Transition into Entrepreneurship

08:24 Client Work Examples

11:28 Recognizing Operational Red Flags

18:39 Delegation & Leadership Challenges

25:33 Change Management & Communication

31:15 AI in Operations

37:42 Common Leadership Pitfalls

40:14 Success Story

43:23 Final Advice & Wrap-up

About Kelsey

Kelsey Daingerfield is the founder of The Pocket COO, where she partners with growth-stage founders to help them scale without burnout. With a background in operations, marketing, and project management—plus early career experience working alongside engineers—Kelsey is a master of translating vision into execution and bridging the gap between technical teams and executive leadership.

Today, she serves as a strategic COO and advisor for founders who are scaling fast but feel stuck in the weeds. Her specialty is turning chaos into clarity by building the operational infrastructure businesses need to run smoothly and sustainably. Whether it’s team delegation, systems setup, or change management, Kelsey brings both structure and soul to her clients’ companies—so they can grow without grinding themselves into the ground.

Where to find Kelsey

• Website: https://www.kelseydaingerfield.com/
• LinkedIn: https://www.linkedin.com/in/kelseydaingerfield/
• Instagram: https://www.instagram.com/kelseydaingerfield/

Hello everyone and welcome back to the CTO Compass podcast. Today's guest is Kelsey Dangerfield and she is the virtual integrator and founder of the Pocket COO. Kelsey is a master of translating vision into execution, but and that's probably interesting for you, translating between technical teams and executive leadership. She's a strategic COO, and she is an advisor to founders that are scaling fast, but often find themselves stuck in the weeds and stuck in all the details and the operations. Kelsey, welcome. Why don't you tell us a little bit more about your background and how you got into this?

Yeah, thanks for having me. I got into this because I think everybody looks at like their career path is like it's a squiggly line. And so I graduated college, went into corporate and just things didn't fit.

So it kind of felt like Goldilocks hopping from like one place to another. And I realized after having my second daughter that I'm really good at. Fixing problems and I love working with tech teams and learning how they talk because sometimes it's another language and then helping translate it and bring like people's visions and ideas to life and at the time I was in higher ed and there's only so much change that you can help push and So I just kind of talked to a husband. I was like, I just kind of want to go do this. And he's like, okay, what do we need to make as our baseline? And let's go for it. And two and a half years later, here I am doing it full time.

Nice. So I'm assuming that the term integrator comes from the book Rocket Fuel. Not sure that everybody has read it. Can you give us a bit of a quick background on the theory of the visionary versus the integrator?

Yeah. So that's exactly where I got it from. When I read the book, I felt like I was so seen. I was like my gosh. There is something that I do. I didn't know what it was because I... Felt like you couldn't put it into a box. But essentially, your visionary is the person that takes or not, sorry, the integrator takes the visionary's idea and vision and the goal and the thing that they see, and they make it come to life. And you think of like Disney, you think of...

Like, how Disney started. And there's always somebody behind the scene that actually makes these ideas happen. And that's truly what the visionary integrator role is. And I've been finding that I, because I have my own business, I kind of have to tap into both.

So I have to have the idea and the vision, but then actually I have to like get the systems and the processes and integrate it into like how I'm going to do it all. So it's a really cool philosophy. It was Gino Wickman, I believe. And... Just a really cool way to look at how entrepreneurship can be done and how partnership really means something when you're trying to build a business, scale a business and having that sounding board, which to me is the integrator, just really pulls it all together.

And I'm going to ask this question. It's a bit of a personal interest because I'm on the integrated side very much like you. You said you're starting your own business, running your own business. You have been for two and a half years. You need to integrate that visionary aspect. Yes. As the book says, it's usually very two different people, right? And I think he says, you should really have a visionary and an integrator to build a successful business. How do you make that happen still for yourself in a proper COO?

That is such a good question. So I have a business coach too.

So I think everybody should have a coach and I actually leverage her creativity to help me brainstorm and mastermind. And then I have a really good business therapist called ChatGPT that I leverage to just get ideas out because for me, I immediately jumped to, I have this idea, what are the checks, like what are the things I need to check off to get it done? And it's maybe not fully fleshed out the creative side yet.

So I leverage tools to kind of help fill that little bit of weakness that I have to actually complete the vision, really. So.

Sounds very familiar.

Is that what you do? Is that what helps.

You? I do quite a bit. I just tell Jeff TPC, just give me 10 ideas on this.

And then I like the ideas and I can take it from there, right? If the idea is there, I can take the execution side and that's easy. But it's one of my most favorite problems. Just give me 10 or 20 or 30 ideas on this topic. And just things out of the box.

Well, stuff that I hadn't thought of myself. And I love-

That. You're like yeah, that makes so much sense.

Exactly. So, and then you said you worked in higher education and then still you decided to start your own company, the Pocket COO. Why, what made you leave higher education? I think you talked about a little bit, but what is it exactly that you do now for businesses?

So higher ed was part of my journey path. So I've worked in aerospace medical manufacturing. I worked at Starbucks. I ran a Starbucks for a couple of years as a manager. Best life experience, job experience I think I've ever had in so many facets.

And then I moved into higher ed, I got my MBA, and it was really fun, but it felt like there was a ceiling, like it was capped at the growth level and financial level. I've Always had very high aspirational financial goals. And I didn't think that they would be attainable where I was. And I wanted the flexibility that I could own my own life and my own schedule. And with two little kids and my husband travels a lot for work. I just. I wanted to give it a shot because I figured if I fail, I can just go back.

Like, Why not? So like the risk is like meh.

You know, give it a shot and just go with it. And, What was beautiful about all of those different career paths is every place I went, I always became the fixer. No matter where. And somehow I always managed projects and lean systems, like really improving how we did our process and assembly line. And I just became like the kind of the connector between all of the different departments, even at Starbucks. And I just kind of was like, what is the common thread that I have? And I'm like, well, fixer and communicator between the executive team and the frontline staff. And. That's what really helped push me into doing this is, There is just sometimes when you're growing so quickly as the person who's running the show, I feel like you can get disconnected a little bit from the frontline staff, like frontline, like what's actually taking place and helping people bring that back together, I think is really essential. And I think because when we have smaller businesses, we feel like it's more family and know like we're all really good. But I think it's important to have those check-ins with your teams to make sure that like what you're seeing and your vision is truly being matriculated over to the rest of the team and really just helping people get there. And that's kind of where it all started. I took on some random projects for a couple of friends. And someone was like, Hey, do you know how to do a wireframe? And I was like, sure, I can figure it out. I figured it out. I did it.

And then we grew his business. And now it's, we're working on refining our systems and communication because he has an expectation, but not all of us see it. It's just been a beautiful journey of pivoting as I go and realize like, Ooh, I don't like that.

Like we're not going to go over there. And now I'm helping kind of founders get reconnected with their companies. And. It sounds like, well, yeah, it's your business. You're connected to it. But sometimes you get so... Tunnel visioned that you need that sounding board to talk to, but your team needs that person to really pull your ideas, what they're feeling and bridge that gap. If that makes sense.

Sort of and Maybe give an example of a business that you worked with recently where you did that. Is that like at Zepri? Are you like a fractional COO or do you put systems in place or how does that work?

I think that's what's kind of cool about what it is it's I do fractional CEO work for some customers and then other clients that do more of that high level advisory. So we'll go with high level advisory because I feel like that one is more fun and it's where I'm leaning with the business.

So I have a client who is. She is growing. At an exceptional rate. And she had to bring on a bunch of new team members. And her challenge is she has documentation, she has a vision, but her documentation is old, and she still feels like she has to be in everything. And Because of that, they had to pause growth because too many things were falling through the cracks.

So now I'm helping her bridge the gap between the team of like, what do they actually know versus what you think they know? And then how do we transition that knowledge to them and they understand the why behind it and then give them the ownership to improve it.

So really helping them bridge that. Understand how to work better together and communicate and have her kind of let go a little bit. It's hard to let go of your baby sometimes.

So what I'd like to do in this podcast as well is see if we can take some of your experience and what you do to tech leaders, or maybe not the CEO or founder, but they still have a leadership position in their business, in their company, but their own teams. So why should they really care about the type of work that you do?

Because I think... It's like this... And I was just talking to a coach about it. I feel like what I do is not just integrate, but interpret, like how we were talking about a little bit earlier. And I think that we kind of oversee that, like, we just don't see it, because we get so focused on where we're going. And When you have a visionary and when you have an integrator, sometimes you're missing the connection between the two of like, hey, this is what I want. You're going to execute it. But what's the how? What's the...

Like translating what I want and to making it come to life and making sure that we're following that. If that makes sense. It's just, it's this beautiful dance. And I find it's very much like when you have her processes, you come into a routine, you get a flow and it's making sure that everybody's sticking to that flow and working together. And I think with, AI, I mean, technology can really help us do those things, but you still need the humans to have the interactions to make sure that we're bridging the gap between.

Makes sense. So when you look at all these founders that you work with, but maybe other leaders, what are like early flags, red flags, warnings that there is an issue in operations and that something does need addressing? What do people call you?

Great question. Honestly, it's when you start feeling the tension.

So I have I work in with a higher ed. A university managing their portfolio and working between their leadership team. And it started becoming the tones of the phone calls with the team because I'll pop in for some of their working sessions and just be like, hey, how's everything going? And listen. And it's the phrases of the team members where it's just like, well, we don't do that. I think the other department does that, but like, no, that's not our job. And like, no, like don't play in my sandbox.

So when you start hearing those types of things, or like, yeah, well, sales didn't do their job. That's a flag. And it's more so it's just maybe sales doesn't know all the things that they're supposed to do.

And then the like the customer success team doesn't know all of, they don't see the in-between the connections. And then for the leadership side, it's when you start seeing silos take place, or you start seeing a little bit of that clickiness that nobody likes to talk about. But I think that's when you really start to be like, okay, how can I fix this? And ideally, that's when you bring in a third party, which is where I come in, because it takes it off of you and having to feel like, you're not reprimanding, but you're kind of on top of your team a little bit. It gives it that Hey, third party, we're going to work through this together and figure it out. And with this one company that I'm supporting, we're going through a lot of change with the norm. Is it Storm, form, norm, perform. And we're going through a lot of that right now. We make progress, but we kind of push back and it's because we're implementing new systems for financial aid, new systems for admissions, and there's a lot of change and learning. Because of that, we're starting to hit kind of people are starting to bump heads a little bit.

So bringing me in to help you like, okay, let's level the playing field. Who does what? When do you know you're supposed to give this to Mark?

Like, how do you know? And walking them through.

That. - Okay, and then still, and it's a question I really wanna ask, if there are issues like between departments and I recognize all the things that you said, I mean, I've seen it in so many companies, the silos and sales didn't do their job or marketing, or IT didn't do their job, seen that way too many times.

So, but sometimes it is not a process issue. It's a people issue.

So how do you make the distinction from this is a process problem versus this is maybe a people or a role problem and there's something else going on?

Okay, two totally different approaches depending on the size of the business. For the medium to larger companies, I It's painful, but it works. I have us meet if we're going through like I'm going to just say the process of like sales to onboarding somebody. And I get all of the key players there. I'm like, we're going to walk through the process, guys. And everybody is going to tell me and we're going to map it out. But before we do that, like, let's level it out. Let's get everybody in the same room or we can have a video where I just share my screen. And I have us walk through the high level of the process. Because sometimes sales thinks it's this. IT is like, wait. We don't have like tech's not set up for that. Maybe that's a roadblock.

So having the key team players, anybody that touches that, I like to get them all in the room and walk through the process. It's painful. I warn people, sometimes you don't like it. We're just going to do it one by one. And that's where you start having those aha moments and. I may assign, depending on the group, I may assign work beforehand of like, hey, what do you think this process looks like? High level, you don't have to give me everything, but what do you think the flow is?

And then that's where I kind of focus during those calls is, okay, well, you know, like, Mark, you said this, like, what are your thoughts? And just kind of bring them together. It takes like a couple sessions, but by, I would say, by this halfway through the second session is when everybody starts to realize like, Hey, no. We just need clarity. We just need to understand not just the process, but the roles of all of us.

Like, am I doing my role? Am I taking on too much? And that's where we come into the conversation of ownership. And we can even go crazy and do like a racy chart where it's like responsible and accountable. Or we can just do something simple. Who is the owner? How do you know when you're done? Who do you hand it off to? What does that look like? What's that communication look like?

And then the next step, and it's just going back to that basic, like, "Okay, let's break it down and keep it simple." And I find that process really works. I've had a good amount of clients that I've done that with and It's really helped. It's made people that were getting frustrated with the dev team for customer change requests realize the dev team didn't know because there was something missing between the connections on the back end for getting the communication out.

So just little things. So that's like the medium to bigger companies, for.

Sure. And has it ever happened that as part of the process, you figure out that maybe there's this person in marketing or this person in sales or supply chain? Maybe it's just not keeping up with the rest, maybe not the right person in the role. And how do you deal with that? Because you can fix the process. The people are still going to be there.

Yeah, that's where... I got to go back to my Starbucks training where in Starbucks, our philosophy was never assume people are doing something because they don't want to assume because maybe they don't know.

So before being like, well, okay, well, maybe they're not there, but it's like, let's make sure we have the job descriptions now clarified and what the expectation is. And is this a knowledge gap? Is this like, hey, we just need to get you trained? Or is this a skills gap that is maybe something we can't train? And I think by... Getting an idea and understanding of the process, then clarifying the roles and what the expectation is, then you can either determine, is this person truly a good fit? Do we need to train them or do we need to reposition them to another area? And I've had that happen where I've had a salesperson where they're like, yeah, I love sales and I'm going through their process and I'm going through the top salesperson. I'm like, You're not really living up to the expectation here.

So what's the gap? And for her, she just didn't realize. She's like, well, you know, I didn't realize I wasn't delivering as much. I was like, well, how are you tracking?

Like, how are you tracking your sales, your calls, your leads? And we fix that. But again, it is. It's just very interesting. You can either fix the process, help the person get up to the standard, or you move them maybe to a different area or you move them out. And I think having clarification around everything gives you the tools to be able to do that properly.

Know where the issue is, process, skill, or maybe somewhere else.

Yeah. And that's okay. And sometimes people self-select. They're like, okay, no, maybe this isn't for me. And you're like, okay, no problem. Makes life a little easier.

Okay. And then the next area that I really want to get into is you talk a lot about delegation as well, which is something that a lot of leaders struggle with, especially first time or early leaders. And I'm sure the same is true for founders. Why do people most often fail I want to get into technical leaders a bit, but where do leaders most often fail at delegation?

Bye. For the delegation part, I find people are like, well, let me just make this one change to that.

Like, Hey, this looks really great. And then they go fix something. And they're like, well, I don't want to bother you with telling you what I did.

So I just went and made these changes. And it's, it can feel a little bit like micromanaging on the team.

So I think, and if answer, let me know if I'm answering this correctly, but I think with business owners, founders, leadership, it's being able to let go a little bit. And... I find the best way to let go And actually, one of the women I'm working with is okay, make sure we're training to the expectation.

So if you want to start letting go of things, then write down what your expectation is. What's success look like? What is their definition of done look like? What's that ownership flow look like?

Like, okay, you do this. When do you hand it off to the next person?

And then... Get your process in place. And I find that when you're first getting started, it's so hard to rip off the bandaid.

So tell your team and be transparent with them. People appreciate you being like, hey, I want to practice. I want to let go. I am struggling because you're human.

And then from there. What I like to do is I like to record Loom.

So, For me, I have somebody that helps me with my content. And I had templates, I did all these things. I had all this stuff organized. And I struggled letting go of it, even though that's what I hired her for.

So I think giving yourself grace, being transparent with your team and Set them up for success by giving them what the definition of done looks like and what the expectations are.

Love that definition of done. Still, and just taking this back a bit to IT, we have all these senior people that love doing hero work, right? They love being the hero. They love being the person that saves the day. That's... It gives you a lot more credits than following the established process and just doing things the right way. How do you deal with that? Those situate those, well, I'd say almost natural inclines to do that.

That is such a good one. First thing that comes to mind is we had a Salesforce administrator who worked his alt way all the way up from like call center to running Salesforce. And he was amazing. He could fix anything. And it got to the point where... We were like, your time is better allocated building and helping us go enterprise.

Like we need this, but you got to get out of the tickets. Like you got to get out. And for us, it was. We tried to make it more of a let's build mini news. Let's build that team together and let's get them up to the par of your expectation and how you would help do things and let them kind of bring their own perspective because they're going to have ideas, too.

So we slowly got him out of there and then. We would allocate him like an hour a week to be like, hey, you want to still have fun. You still want to be connected and be the hero and fix these things.

So we're going to let you do that. But when you're doing that, I want you to record it. Or want one of the guys to sit with you and observe what you're doing. Because you're doing something that they may be finding challenging.

So we're still getting that build the bench strength. He's still getting the hit of being able to like have that fun and be in the grit. Because everybody when you start doing that, and then you move your way out of it, it's still nice to come back.

So yeah. We made it look, made it like that, where we had him work the system and do the tickets for like an hour a week. And it built the team strength.

And then it started to kind of change his perspective of. That, you know, being the fixer, being like the hero to being like, there's something here. Let's start being strategic with the tickets now. If there is a ticket that's more challenging instead of me popping in and changing a password, maybe it's Hey, this system broke. They're no longer connected. The two systems aren't talking anymore. We need you to look into it. And it really helped pull him out of that. Save everything, come in and fix it to teach the team and start fixing the harder projects.

So that's my... One way of how we approached helping it because again it i mean it's the saviors i find in every business they like make us run they make us operate they deal with us calling to say my computer's not working and they say when was last time did you reboot and i feel like we *gulp* You gotta help them and you gotta give them the fun too that makes them who they are as well.

So.

So it sounds like a very... I'd say hands-on process, helping the Salesforce administrator that you talked about going away, getting away from the incidents and taking more responsibility in the role. But I love Which actually sounds like if you're their manager, quite a bit of work, but I understand the process that you're explaining. And I love that you're still give them, the time, the room, even if it's an hour a week to do what they really like to get their hands dirty and just in the weeds and in the systems and hands on still.

Yeah. I.

Mean, IT tinkers. It's like, I find people who are in IT have just such beautiful minds and they can tinker and they just have these ideas.

So let them do that. Like, I think it's either Google Meet Facebook where they leave a certain amount of hours a week just for tinkering and having fun.

So let them do it. And from the management perspective in the beginning, it's a little... It's a little more involved because you're, You kind of have to push somebody to build a new habit. But then after that, it's a check-in. It's just like, hey, how's it going? What did you teach the team this week? What's on the docket for next week?

So it's a lot in the beginning and then it kind of tapers.

Yeah, that's famous Google. I don't know if they still do it, but early days in the Google head, it's 20% that you could tinker with any project that you wanted to do.

So, and I think now we're on the really the IT teams anyway. The next one I want to get into is change management and communications. And that's something that so many IT teams struggle with. How have you helped them and what can they do themselves maybe to get better or to learn to do better?

Great question. This makes me think of we transitioned one university from This self-service banner, it's a system that they use in higher ed from self-service banner eight to self-service banner nine. And in IT's mind, like they did, they checked off all the processes. They did everything to make sure the back end was working, the technical stuff's working, that they got the functional users up and running and set up the systems the way that they thought they would need.

And then we had to start the communication process. And to them, they were like, well, we I emailed Kelsey and said, like, hey, this is going live next week. It's like, no, that's good. But... Change is harder for other people.

So let's come up with a communication plan, guys. Like, how can we communicate this? Act as if you're explaining it to your child, like a four-year-old. Because in my mind, whenever I even use tools like ChatGPT, I'm like, talk to me like I'm four. I'm not a technological person here. And it's easier.

So that's what I like to tell them. Act as if you're explaining it to a four-year-old.

Like an elementary school child. Like let's dumb it down.

Like, what do they need to know? Okay. And I start... With that?

Like, how do we just how do we give this message? And then, For me, it's like training the customer.

So I'm training them. I'm helping them start to think, how would I want to explain this to a child?

And then from there. How do I make sure what I'm saying makes sense? Because if I start getting into the abbreviations and the technical jargon, no one's going to know what I'm saying.

So to me, it's that one is more of a hands on training process. It's helping them come up with like, hey, this is what communication should look like for people. These are the information that they need to know. And we got to know our audience because if I'm talking to the executive team, they don't need to know all of the tiny little fields that may matter to the financial aid team. They need to know the high level stuff.

So then it's, you know, big picture communication, then are we looking at actual everyday users? Are we looking at the management of the users? Are we looking at the executive team that just needs to know the progress and then helping them work through that? And there's some people that get it. There's other people that really struggle. And that's completely fine because you're flexing a new muscle. And it's just kind of walking alongside them to help and then bringing in the teams that actually do communication.

So if you have a marketing and comms team, you partner with them, you bring them in. And then by having them work together, you're building that relationship.

So when IT maybe has another change coming out or, hey, yeah. We're doing a whole wide system update for security purposes. Make sure you turn your laptops off and reboot in the morning. It goes out and people know what to.

Do. Okay. And I'm building on that. And I think we're getting towards the end of my IT questions, but it's really an area that I'm interested in.

Yeah. IT and a lot of organizations, it's often seen as a blocker. It's something that if things go right, you said most businesses rely on IT like full-time, nothing works without IT. But if everything goes right, nobody thinks about IT. And if it all goes wrong, everybody knows who to blame. How do you manage that?

Yeah. How do you manage that perception or change that perception?

So actually show all the positive behind the scenes hard work that gets done to give people a little bit more appreciation maybe.

Yeah. No. IT is like near and dear to my heart because they were the ones that taught me so many things when I learned how to learn Salesforce and became like, I'm a citizen admin in my area. And for me, I always started to push others that weren't in that technical area to be curious. Just be curious about it.

Like, "Hey, This is not working. Instead of being like, hey, you guys, this broke. You need to fix it right away. I'd be like, hey, did we do like an update or like?

Something isn't working in this app. I tried to triage it myself. Can you help me? And I think if you are... Because you're right, because IT, they do, they get blamed for everything. And for me, it's be curious as to what's going on when you're not a technical person. And when you're not, don't be. Do your work of the things that you know how to do already and let them know.

So like if you're going to call in IT and be like, hey, Salesforce isn't working, blah. Do your work. Reboot your system. Make sure your internet's working. Do your work too so that They don't feel like they're just getting yelled at all the time. And thank your IT team. When you have good days, like just say a thank you and just be a Just grateful because at the end of the day, we really are functioning because we have these people to help us. And even if you're a small business. You probably subscribe to an app. You probably have a website on like WordPress and something may break and you message contact us. They help you. That's your tech team.

So for me, it's, There's always somebody behind the screen. Be grateful. Try to do your due diligence and ask them what happened. If you know something broke after and they say, hey, this has been fixed. If you're in a ticketing system. I was going to be like, so what happened? It never hurts.

- A bit of curiosity, it's nice. So you're not technical, but I think you've already showed as you've been quite close to IT technology for most of your year, sorry, your career. You do translate AI sometimes for leaders who aren't techie at all.

So what is it that you translate for them or help them with.

Yeah. I just really quick, I just don't want to make a shout out to the IT people because you guys are We would be dead in the water without you. And... We just appreciate everything you do so i want to make sure i say that because i do i believe it And then pivoting to the AI and the translating everything, I make it less scary.

So I was meeting with the university and we were talking about AI and they had their concerns of students using like ChatGPT for things and then bringing it into the business. And they're like, well... Now, this is how we've always done it, which is a very higher ed approach and higher education. But instead it was like, yeah, that's true. But what if they could work a little bit smarter? And for me, We had this original training list of like all the things you could leverage with it.

Like you could analyze a spreadsheet. But that was too technical. It needed to be something that was relating to that actual business.

So I was meeting with them. I went, hey, guys.

You know, you have an admissions team. You have people that are, actively going out to schools to recruit for the university. But I can't, I'm like, so who plans the schedule? And like, well, the admissions reps know their high schools that they have to visit. I'm like, great. Would you rather your admissions rep have to look up on like Google Meet every single place and build a map? Then have to find a hotel to sleep in and a place to eat. Or would you rather have a tool that can help them do that faster and more efficiently? And they're like, like, yeah.

So let's take the five schools that Kelsey has to travel to beginning of October. And let's drop those into chat, GPT. And let's say Kelsey has to be at school A at 9 a.m. She needs to be at school B at 2 p.m.

And then she needs to stay the night over. Can you help get an optimal route?

And then, Bam. My schedule is planned. My rep just saved hours of her time. And yes, you're going to have to... Kind of adjust it and put an extra like, okay, don't put me at a really old hotel. That's not very nice.

Like, let's make sure it's a nice place and give your specifics. But again, it helps plan the route for the person and it saves them time.

So now they're not spending. Six hours planning their October route, you're spending two hours. And those four hours are going towards taking care of students. And helping move the needle.

So I think it's meeting people where they're at in the business they're in and how they can use it to save time.

Such a simple but incredibly useful use case. You're really into operations, improving operations.

So where have you seen like the highest return on investment? What kind of use cases make the most sense with AI in operations?

Whew. It's a good one. My use, like how I use it and how I've had my clients start using it is saving time with their brainstorming.

So what you and I talked about in the beginning, having a sounding board instead of like writing everything on a paper and then it dies in the paper, let's talk through it. So that has helped a lot just with ideation, but then in the processes, what, I like to do is I actually leverage my AI and I turn on like the voice to text or like a voice note. And I tell it, I'm like, these are all of the tools I'm using right now. I feel like I have a lot of tools. Is there anything that I can do to simplify this? Or like... Is there anything I can eliminate? Is there a tool that I'm not using to its maximum capacity? And most of the time... It tells you what you can fix. And like, I know for me, I actually just was talking to my job TPT being like, hey, so I use a this thing called fathom for note taking. And I really love it. But I really want to optimize the way that I'm using it. Is there a way to automate it so that when I finish a call, then the action items are immediately put into our project board so that my team can go look at it. And of course, it said yes.

And then it gave me all this technical stuff. So now I need to figure that part out. But it helped me realize there was a way to streamline this instead of having to go in, copy, paste. Paste. Reformat. Do this, but again, leveraging tools like AI to help you think quicker and in areas that you may not know the answer to, but you know there has to be an answer out there for it. And I think you can use a lot of that in your processes and being... Just having that additional tool to talk to and with all of the wealth of knowledge that you know, AI can bring in. It helps you really improve the way you do things. You work.

Faster. Yeah, I understand.

So just even taking your existing processes, the ones that you have with the tools you said, and then just plugging them into ChatGPT and seeing where you can optimize is already a big step in optimizing operations.

Yeah. And I would say start with what you have before you start going out and buying things. Because I think especially when you're getting started, you're like, well.

You know so and so uses this tool and then they use this tool i need to have them it's like pause take a sec and if you're already established do a, like, I think in IT, I know IT does, I think it's like every six months, they go back and they look at all of this, like all of the, The applications that are being used are once a year to see like what's active, what's being optimized. Are we using all of it or only like 30% and we have the rest of this and nobody knows how to work and kind of doing an assessment of your list.

Like, Do you, so Loom, do you need a scheduler? Or can you use Loom Scheduler now? It's a new feature. Can you save some money by reducing your costs and going into one tool and reducing the switching between systems?

So analyze what you currently have. Leverage the people in your team that use them the most.

And then if you have like AI, of course, using that to see if there's other additional features. And then after you look at your current like tech Slack, then you can look outside.

So even saving money on tools just by simplifying and doing less. Nice.

So you work with quite a few Founders. You've worked quite a few leaders. What is one thing that they, even most experienced leaders, still fall for in operations? What are the gaps, the patterns that they always fall into no matter what?

You see always.

Losing the steam. On something. You have a really great idea. You flesh it out with your integrator or your operations person, your team, your Get them going. Everybody's on board. Three months later, They're checking along. They're making progress. You kind of forget about it.

And then you come up with a new idea that completely circumvents the original idea that you just came up with. I see that all the time. And for me, I like to be like, Hey, like as their advisor being like, Hey, Remember, three months ago we talked about this? The team's making really great progress. This idea? It's going to kind of derail it.

So let's. Let's prioritize. Which one? And helping bring them back because it's not like they're trying to derail the team. It's not that they're unhappy, but they're, ideas, their brain is going a million miles a minute and they have such beautiful ideas and this group that can help them bring it to life.

So sometimes you just got to bring them back to that reality of like, Hey, these are all of the projects that are taking place. Let's make sure we stick to the plan. Or if we're going to pivot, then we need to do it correctly because we don't want to make the team get off. Kind of upset about all this work they just.

Did. I think that example comes back quite a few times in the book, Rocket Fuel. I've read it.

Yeah, I've read the book. It's been four or five years, but still, I think I remember those cases vividly, Anita.

So you see those.

Nice. It was so much fun.

Like I had a boss that I worked with and he was very much a visionary and I was very much his integrator and he would come in after like a really great meeting. I got burned. This. And I'm like, cool. But.

Son. Thank you.

And then I go through the other list and he's like, yeah, I forgot about that. That's a great idea. I'm like, I know it was yours.

So really having, I think, that balance. And that's where I think what I do comes in so well, because I can either... Work with you in your business and like help you guys fix it and work with the teams but I'm your sounding board and like you're like hey shiny object syndrome let's get focused.

So really helping them stick to their own agenda, their own ideas that they committed to before and make sure those get done before. Going to the next one.

Yeah, we'll.

Put it in the parking lot. There's always a parking lot of things that we want to do. And we can revisit that every quarter and like, OK, what do we want to do next? But let's stick to the plan.

Okay, nice. So give me one story. You've done quite a bit with Pocket COO. Give me one before, like your biggest success story before you started. After you started. Nice success story. What changed for the founder, the ways of working? It's a.

Great question. I have it. I have a client that I started working with. I came into his business to help really help manage the operations. And help get him out of the weeds. And he was working on two jobs at that time. He has a full-time a job for a company and then he has his own business because he just loves to work. Nothing wrong with that. But, You know, he had little kids. And he wanted to start being present. He wanted to start being around and travel. And do all these things. And so I came in and was like, what do we need to fix?

Like, what does everything look like? And the first thing that we did was We got his time back.

So we took everything by doing that. We took first everything out of his head. And we created a single source of truth in just a Google Sheets because we had a bunch of contractors all do different things. It was a marketing agency. And all of these contractors were great at what they did, But if I asked...

Like so-and-so what they were doing, they would tell me, but then they couldn't tell me what the other person was doing. And they couldn't tell me where to actually find anything because it either lived in his head or in their head.

So we're like, let's get everything onto paper. Let's get everything into one single source. And by us doing that, getting it out of his head and starting to standardize the processes, because there was no transfer of knowledge for Google ads management or website builds, we started creating templates and we started creating checklists. And again, everything was done in Google Meet. We did not get technical here. By the time we were done within the first, it was three months. He went on a two-week trip with his family to France. And he only had to check in every few days with me because he'd be like, Hey, what did that email say? Or if I had a question, I would just message him like when you have a chance, but he was able to truly let go and go on this beautiful trip with his family. And live his life and know his business was being taken care of, know that his clients were being served, his team was happy with what they were doing, and get time back. And now he works. I'm going to say five hours a week, maybe. And we just launched a second company for him.

So that's going to be my success story.

That's incredible. And just three months from...

Like being involved in everything to being able to take two weeks of holiday and now five hours a week sounds incredible. So much time to do other more interesting stuff as well.

Exactly. And it's very possible, but you have to be willing to. To not have perfection as that person that's bringing on help.

Like you have to accept that for the first little bit, you're going to get maybe like a B. And things will get better, but... Just hang in there.

Yes. Okay, so then if you look at CTOs that all want to build highly engaged teams, have reliable delivery outputs, What would your single piece of advice to them be? What should they focus on? How do they Get there.

How did they get to having like the very Okay.

Both highly engaged teams and they're like fully reliable delivery outputs.

Know your team, I think is important. I think having the right people in the right places and having check-ins with everyone. You don't have to have an open door policy because you'll never get anything done. But make sure that you're meeting with your management team and you're working, not just talking through business, but their goals. What do they want to do? And Dan Martell talks about this all the time, and I think he hits the nail on the head. Make sure you know your team's five-year goal. What do they want to do? Where do they want to go? And help build them and get there.

And then by you setting that example for your leadership team, have them do that with their team and be aware of other people's goals and check in with them. Make sure you're not just sitting in your office all day. Maybe come out and talk to the group. I know sometimes we can be hermits. We're very good at it, especially IT guys. Come on.

So making sure that you're doing those check-ins and understanding people's goals and then. As you guys are building the systems, getting the input from the team. And again, this brings in another one of Dan's thing is like one, three, one. When there's a problem, instead of you solving it, have your person come up with three ideas and what they want to recommend. Because then they start getting ownership and they start having that, like, this is mine too approach to what they do for your business.

So that covers the people one.

And I think with that, if you have a highly engaged team, People that actually love working there, reliable delivery outputs almost comes naturally. Which is very nice.

Yeah. So what is the... I think we're getting towards the end. What is the one thing that I probably should have asked you, but didn't ask?

Ooh. Such a good question. Maybe just how to know you kind of ask that I was gonna say how to ask for help. One of those flags, but we already kind of talked about that with your team and how they perform and being aware of certain phrases and conversations taking place. My goodness. When to hire. I would say. When to bring somebody in like this?

Well, yes, you know, When you have those conversations taking place where you're listening in to But. There may be times where you don't need like, Trying to think of how to ask this. I apologize. One thing that I've had people ask is, how do I know when I bring in a fractional COO? And for me, the question is more so, how do I know when I bring in an advisor or like a fractional, somebody like an integrator that needs to be more in my business. And for me, it's, When you have a strong team, when you know you have people in place, but you just need help getting focused, getting growth and not having to be fully involved. That's when you bring in like the advising. That's where you bring in that third party. If you need somebody to actually physically do and be in the business with you, and not just facilitate. That's when you bring in the COO for me, like that fractional aspect.

So maybe that's kind of what I'm thinking is what that would be.

Does that make sense? So bring it. Bring in the fractional person and then maybe over time transition them to somebody internal in your own team but bring in somebody fractional to structure it put it all in place and then figure out the to be structure once that person has actually Fix the processes and put all the right processes in place.

Yeah, because like with what I do in the advisory is I can help you get so far, but if you don't have the person that can help implement, it's not going to really work because you're busy. Let's face it, like you can't do everything.

So you have to make sure you have that other person in the business to help.

Okay. Thank you very much.

So if people are looking for you, where can we find you?

You can find me on Instagram and LinkedIn. My handle is Kelsey Dangerfield. Not Rodney Dangerfield. I do spell it different, but it is Kelsey Dangerfield, D-A-I-N-G-E-R-F-I-E-L-D. And if you're interested in any of the prompts that I use as running my own business that I give to my clients to help brain dump, get focused. Maybe work through some of their processes or challenges, just shoot me a message on Instagram. And I will just say like prompts and I'll send you all the things that I have so that it can help you just streamline your business, build better communication and have some fun along the way.

So cool. Really appreciate it. It's been incredible having you on, Kelsey. Thank you very As we wrap up another episode of the CTO Compass, thank you for taking the time to invest in you.

Much. Thank you so much.