What does it take to shift from transactional sales to transformative customer success? In this episode, Melinda Lee chats with Andrea Bumstead, VP of Customer Success, about her journey from marketing and sales to leading long-term customer relationships. Andrea reveals why she chose customer success over sales, and how this helped companies scale from 15M to 50M.

In This Episode, You Will Learn:

The Power of Long-Term Relationships

Andrea's pivot from sales (transactional) to customer success (relational):

"I value relationships more than deals. In customer success, you partner with customers for years, not just until the deal is signed."

Key difference: Sales is a one-time thing; customer success keeps them coming back.

The 40-Year-Old Epiphany

"At 40, I stopped apologizing for who I wasn’t and started leading with who I am." How authenticity unlocked her confidence.

Scaling Companies

Andrea’s non-negotiable strategy for client retention: "Treat every customer like a 10-year partner, not a one-time transaction."

The Best Investment

Learn why she hired her own executive coach - and how spending $5,000 on self-development led to a $50,000+ salary increase! A clue? Difference in communication style.

Connect with Andrea Bumstead

LinkedIn Profile: www.linkedin.com/in/andreabumstead 

About the Guest: 

Andrea Bumstead is a transformational leader who thrives in the chaos of scaling, turning Customer Success into a growth engine for SaaS companies. With a track record of scaling organizations across FinTech, EdTech, and beyond, she’s a builder at heart, obsessed with momentum (her 70% Rule > perfection) and empowering teams through trust.

Fun-facts:

• 🐄 Grew up on a 100-cattle dairy farm in Ontario.
• 👨👧👦 Mom of 3 (2, 5, and 8) who took all three kids to Asia for a month last year.
• 💘 Met her husband at her first job out of university. 

About Melinda:

Melinda Lee is a Presentation Skills Expert, Speaking Coach, and nationally renowned Motivational Speaker. She holds an M.A. in Organizational Psychology, is an Insights Practitioner, and is a Certified Professional in Talent Development as well as Certified in Conflict Resolution. For over a decade, Melinda has researched and studied the state of “flow” and used it as a proven technique to help corporate leaders and business owners amplify their voices, access flow, and present their mission in a more powerful way to achieve results.

She has been the TEDx Berkeley Speaker Coach and has worked with hundreds of executives and teams from Facebook, Google, Microsoft, Caltrans, Bay Area Rapid Transit System, and more. Currently, she lives in San Francisco, California, and is breaking the ancestral lineage of silence.

Website: https://speakinflow.com/

Facebook: https://m.facebook.com/speakinflow

Instagram: https://instagram.com/speakinflow

LinkedIn: https://www.linkedin.com/in/mpowerall

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Welcome, dear listeners, to the speak and flow podcast, where we dive into unique strategies and experiences to help you and your team unlock the power of your voice to achieve maximum potential and flow even in high stakes situations. Today we have Andrea Bumstead. She's amazing leader. She's a vice president of customer success.

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Melinda Lee: specializing in organizational transformation. Hi Andrea.

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Andrea Bumstead: Hi! Thanks so much for having me, Melinda.

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Melinda Lee: I am so excited, and before the call you shared about your journey toward being a Vp. Of customer success, I'd love for you to share that fascinating story. What was that defining moment that told you? This is what you're meant to be.

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Andrea Bumstead: Yeah, that's a really good question. I think without going into too much detail, I actually started my career in marketing and sales.

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Andrea Bumstead: Which I really loved. In fact, I call them my second loves all the time because they hold a very special place in my heart, but I think for me, I really realized that I value relationships and long term relationships. And so the ability to have that with customers.

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Andrea Bumstead: I value just a little bit more than sales. There's still things that I love about sales. But what really won me over in customer success was the long term relationships that I could build with customers.

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Melinda Lee: I love that. And so that's what made you decide to. Trans. What's the difference? Like just having a long term versus the short term.

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Andrea Bumstead: Yeah, I mean, sales tends to be a little bit more transactional. And it's an enterprise sale. You know, you basically get the customer in the door, you convince them to use your solution, and then you pass them on, whereas customer success, I mean you can have the same customer, for I mean ideally, 5, 10.

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Melinda Lee: Yeah.

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Andrea Bumstead: Years right? And so you get to know that customer on a much deeper level. You're engaged with them for significantly longer. So that's the piece that I really liked about post sales and customer success in particular.

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Melinda Lee: I love that, and that's why companies bring you on to develop that journey. The customer success journey. And you've helped companies scale quite a bit from 15 million all the way to 50 million. And so what has been your key to success in communication? Do you think.

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Andrea Bumstead: Yeah, that's a great question.

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Andrea Bumstead: really. Well, I kind of go back. At 1 point in my career I decided to hire an executive coach. So it was when I was a director. I knew that I wanted to move into being a vice President. I really wasn't sure how to get there. But I knew that what had got me to being a director wasn't going to get me to a Vp. And one of the key things that I learned from my coach.

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Andrea Bumstead: Is that really the difference between a director and a Vp. And a Vp. And a chief customer, officer or chief customer officer and the CEO.

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Andrea Bumstead: Apart from experience, the one difference is how they communicate and that's something that always

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Andrea Bumstead: stuck with me. And through her coaching program. I really started to reflect on how I communicate and as I sort of did the the hard work to get, to know myself, to go through her coaching program. I noticed a really big difference in my communication style, and so I would say, that's been my one sort of key to success as I've moved sort of up the ranks.

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Andrea Bumstead: Is is communication.

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Melinda Lee: Wow! I love that. And so let's break that down. What was it like communicating back? Then, do you think?

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Melinda Lee: Yeah, I cringe.

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Andrea Bumstead: That question because I wasn't the best communicator back then, and I mean I thought I was a good communicator like I would get in a room, and I would always speak up, and I would have an opinion and you know I I took a lot of ownership, but I think why I cringe is that communication came from a very insecure place.

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Andrea Bumstead: came from a place of like need, feeling like I needed to prove myself feeling like I had to speak up in meetings that I should speak up at meetings, or you know all that internal self talk of like you're the leader of this team, you should have an opinion.

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Andrea Bumstead: and so that's why I cringe a little bit because it didn't come from a really great sort of authentic place. It came from a place of almost like imposter syndrome like, I don't belong here. I don't deserve to be here, and I constantly need to prove otherwise.

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Melinda Lee: Yeah, it's so fascinating. Because, yes, where we're speaking from, who are we being? Yeah. If it's from insecurity, it could tend to overcompensate over, speak over, communicate, speak, just to prove something. Speak just to speak, because, like you mentioned, you're you're driven from, I need to bleed, and I need to. And so that means I have to have an opinion.

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Andrea Bumstead: Wow, yeah, yeah. And I would say, one of the things that I learned is that it wasn't serving me, it wasn't actually, working I wasn't being valued as a leader. I wasn't felt being valued for my opinions. I was anxious in meetings, so it would just it wasn't actually

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Andrea Bumstead: working, despite how hard I was trying.

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Melinda Lee: And then so what did you do to make that transition.

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Andrea Bumstead: Yeah, I would say, it's been gradual. So it's not like, you know.

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Melinda Lee: Right.

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Andrea Bumstead: One day I woke up, and I was an expert communicator who had, you know, everything all together. Feeling really confident. I think it really came from a place of experience. But then also a lot of internal work. This, you know, really working on myself, that I don't have anything to prove. I don't have to speak in every meeting. Sometimes it's better if I just listen. Sometimes it's better someone else speaks.

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Melinda Lee: Bye.

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Andrea Bumstead: Just yeah. Being more authentic with myself, knowing who I am. Really helped me sort of increase my confidence over time that, like.

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Andrea Bumstead: I don't need to prove anything, and I think you know the later I get in my career, especially when I turn 40. I was kind of like I. This is it. This is all you get. This is who I am like. I don't have anything else to prove. And I was just tired of

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Andrea Bumstead: approving myself. So yeah, I think now, as a leader, I show up a lot more authentically, although I do have to say like, not every time. Sometimes I fall back into old habits, and that's kind of normal but for the most part I show up more more from who I am as a person, and not trying to prove.

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Melinda Lee: Right. And so what would be your 3 tips to prepare for a high stakes? Presentation? What do you do.

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Andrea Bumstead: Yeah, I think one is preparation. You always feel more confident when you have prepared. I do I am careful, though, because I tend to over prepare, and that also isn't a good thing. And so I try to kind of get the right level of preparation if you will.

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Andrea Bumstead: The other thing I do is really positive self talk before presentation. So I will say, thanks to myself, like Andrea, this is where you shine. This you you've got this. You have done this before. You're an expert communicator. Whatever. Sometimes I do a power pose not often, but sometimes anything that really just helps me

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Andrea Bumstead: feel sort of deserving to be in the room confident. I'll also on the flip side, if I'm feeling a little bit

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Andrea Bumstead: not confident. Then I I do try and reflect on why that is so why am I not feeling particularly confident? What am I under the surface telling myself, you know, like you're gonna mess this up. Someone's gonna be better than you. You don't know what you're talking about. You're gonna be thrown a curveball question. And then I have to.

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Andrea Bumstead: you know. Then talk myself out of that where I'm like. No like you know how to handle curve ball questions. You don't know the answer. That's okay. So preparation, self talk. And then, when I'm in the actual presentation, I do try and pay attention to my body which might sound a little bit strange, but it's I know that if I start to get anxious.

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Andrea Bumstead: or nervous, I start. I start to get hot. I'm like, oh, it's like a little bit too hot, so I get warm. If I get really anxious I start to get a little bit shaky. Which is not good. And so in those moments when the other person is talking, I really try to take a breath.

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Melinda Lee: And.

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Andrea Bumstead: And if I can just give myself a couple lines of like Andrea, you got this, or like that was tricky. Let's move on, you know, you still have time to salvage this. It's gonna be fine. Take a pause like whatever I can tell myself in those like

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Andrea Bumstead: really quick seconds while someone else is speaking and still be paying attention. I try to get my mental state back to where it's helpful, because a thought is what triggered the anxiety. And so I try, and really quickly. Can I counter that thought of like, oh, this isn't going well, or Oh, my God! I can't believe they asked me that, or I don't think I answered that. Well, like I just try and counter it like right away.

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Melinda Lee: Yes, I love those. Those are powerful tips.

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Melinda Lee: amazing. So, beginning from preparing, but not over preparing, because I find that when we over prepare. We try to

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Melinda Lee: put everything in a box like this is how it's gonna go. And it's not the case. And then so we get veered off. We're gonna get thrown off. So just preparing. But then, knowing you have all the tools and resources to be in the moment in case things go differently.

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Melinda Lee: Secondly, positive self-talk, right? Going into presentations with a negative. This is going to go awry. This is not going to go. Well, then, you might lead yourself there and manifest and create that. So, having positive self-talk, I've got this, my voice matters. And then, being in the moment going into the situation, noticing your body noticing when you're feeling anxious.

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Melinda Lee: and I say this, all the and people try to avoid it, or they try to suppress those emotions. I love what you said, like when someone else is speaking, give yourself that time to actually acknowledge that feeling inside the body that is your cue, to slow down, give yourself a breath.

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Melinda Lee: Acknowledge that it's there. Sometimes I'll say, Oh, yeah, I'm nervous. I'll say to myself, I'm nervous right now, and just noticing it. And then, when you actually call it out in your mind, then, or your body, then it actually dissolves, it actually will neutralize itself. And then transitioning into, I've got this. Oh, yeah, that was uncomfortable. But we can. We'll move. We'll think something. You know. I'm here. It's okay. Be present.

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Andrea Bumstead: Yeah, yeah, I do. I do tell myself before presentations to like Andrea, you're an expert at winging things.

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Melinda Lee: Yes.

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Andrea Bumstead: Wing it. You're like, you're great at this, just wing it and.

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Melinda Lee: Right, right.

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Andrea Bumstead: I'm not an expert at it, but just by telling myself like, it's okay, you can wing it. You've winged it before, like.

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Melinda Lee: You know.

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Andrea Bumstead: Confidence will trump everything like just whatever I can tell myself to just be like. It's fine like I. I can't anticipate everything that will be asked or how someone might react. And I do try and anticipate. Well, I try and prepare to that like if something does go awry right? Like, if I truly don't. Yeah, I don't know.

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Andrea Bumstead: Show up. Well that have the right answer. Feel like I got put in the hot seat. It's okay to like, pause in a conversation and to say like, Can I can? Can we try that again? Or when I get back to you with a little bit more information on that, or I'm not sure I represented that. Well, let me kind of come back to it. So there are things that you can do to also recover. If you will.

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Melinda Lee: Right to have in your back pocket. So that way you don't have to overcompensate. Prove yourself.

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Melinda Lee: and you can be in the moment and be flexible and problem solve and get curious, even if you don't have all the answers.

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Melinda Lee: It's those moments when you go in there and you pretend, and you overcompensate, and you cheat. Need to prove. Then that's when it gets

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Melinda Lee: uncomfortable and things it's it's difficult to try to bounce back.

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Andrea Bumstead: Yeah.

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Melinda Lee: Yeah.

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Andrea Bumstead: Percent.

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Melinda Lee: I love that well, Andrea, that was so powerful, and I appreciate you sharing your experiences. I know that I've certainly felt that way, and I know that our audience also feels this way, too, and it's high stakes, conversations. You want to do well, and there's a lot at stake.

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Melinda Lee: and we want to be able to get to a place where we resolve problems and collaborate with people, and so having the right communication

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Melinda Lee: is different. It is going to be different when you move up the ranks, when you get to a higher level, and having that using communication as a tool

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Melinda Lee: as your your competitive advantage, your strategic advantage, or just as a good leader, it's important.

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Melinda Lee: So I'd like to ask you what I like. Ask all my guests at the end is, what is that? One leadership, golden takeaway that you want people to remember.

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Andrea Bumstead: Oh, what is that? One leadership? Golden takeaway? Maybe. I'll go back to my coach for a second. So early in my career. I had a mentor, and she told me that I would need to spend money on myself and my career in order to move up the ranks or not necessarily move up, but but to have the career I wanted I would need to invest in myself.

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Andrea Bumstead: And as a very young sort of Green Leader.

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Andrea Bumstead: I didn't take well to that, like I I really like, I thought.

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Andrea Bumstead: isn't that kind of the company's job to invest in me and to help me become a better leader like, or isn't that what professional development funds are for, or like? I just. I didn't think that it was truly my responsibility.

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Andrea Bumstead: And I also couldn't fathom spending money like she was like, you're going to need to spend money on associations and coaches and resourcing and learning, and all these things. And I will say, the more money I've spent on myself, the higher my return has been like I. It's so

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Andrea Bumstead: it. It's so true like you need to invest in yourself and not do it alone. Like you know, you need. You need help. Everyone needs help, and to expect that that would just

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Andrea Bumstead: come from a job.

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Andrea Bumstead: That's not true, like you know. I I hired a coach because

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Andrea Bumstead: I wasn't getting the coaching I needed.

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Melinda Lee: Yeah.

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Andrea Bumstead: My job. And yeah, there's some onus on the company. But really

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Andrea Bumstead: the onus was on me to fill those gaps, to figure out what I needed. And so I've definitely invested in my career. So if I can give one little tidbit of advice is you can never go wrong investing in yourself.

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Melinda Lee: Love that I love that I mean it's so true. I'm I'm a solopreneur entrepreneur, and

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Melinda Lee: I know that when I invest in something, then I am going to give it my 100 to really capitalize on it and going back to what you're saying when you are responsible for your own development and leadership and and finding the right people the right resources and and investing in that. You're going to get that Roi, because you're putting in that money you're putting in that capital. Then you're going to spend. You're going to definitely have more

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Melinda Lee: commitment, more dedication. And then and then, especially if you're picking the people that you want, and the skill that you want to take yourself to the next level versus waiting for something to happen, waiting for someone to give that to you.

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Melinda Lee: Yes, and the Roi. Yeah. And that's going to propel you faster because you have people that have already been there done, that experts on your side, and the team that's on your side.

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Andrea Bumstead: Yes, a hundred percent. It's so funny. The sun, just like as I said that, just like beamed.

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Melinda Lee: Andrea, you're ready to shine. That's why

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Melinda Lee: you're ready to shine. You're you're meant to shine

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Melinda Lee: well, thank you so much for your time, and I have learned so much, and I appreciate you sharing your story with us, and thank you audience, for being here. And remember, anytime you have a chance to communicate. You have an opportunity to connect, to inspire, and make a positive difference in the world. I am your sister in flow until next time.

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Melinda Lee: Take care. Bye-bye, bye, Andrea. Thank you.

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Andrea Bumstead: Hi! Thank you.