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"Our job is to do great things" - Maia Josebachvili, Chief Revenue Officer of AI at Stripe

Executiveland · 2026-05-21 · 38 min

0:00--:--

Key moments - from our scoring

Substance score

55 / 100

Five dimensions, 20 points each

Insight Density11 / 20
Originality10 / 20
Guest Caliber16 / 20
Specificity & Evidence9 / 20
Conversational Craft9 / 20

Maia Josebachvili draws on eight years at Stripe across roles spanning strategy, HR, enterprise sales, and now AI revenue to outline how senior leaders operate when there's no established playbook. Her core thesis: authority isn't handed down; it's earned by building trust, surrounding yourself with exceptional talent, and getting to ground truth through direct customer conversation. She references her background as a competitive skydiver (750 jumps) to illustrate the "default to trust" mindset that enables teams to move at speed under uncertainty. When moving into unfamiliar territory - she's never been a traditional CRO, yet leads AI revenue - Josebachvili's strategy includes assembling a "phone a friend" network of admired peers in that role, hiring domain experts (like George, her deep AI sales leader), and maintaining humility and curiosity. She emphasizes the importance of sleep, exercise, and a strong internal support network to handle the "surge moments" that come with senior roles. On Stripe's AI strategy, she frames the company as building "economic infrastructure for AI," serving both AI founders navigating monetization and global expansion, and enterprise brands rethinking commerce through agentic AI - citing 85% of retail conference attendees now pursuing agentic commerce strategies. She also serves on Dartmouth's board of trustees.

Key takeaways

  • →Default to trust as a foundational team operating principle, enabling fast decision-making under uncertainty, but verify quickly if integrity falters.
  • →Success in unfamiliar senior roles requires assembling both a sponsor network and an exceptional team with domain expertise you lack, plus disciplined use of your own time on ground truth.
  • →Modern leadership means operating full-stack - holding vision and strategy while diving into specific customer friction points and problems to inform organizational priorities.
  • →Agentic commerce (LLM-driven shopping) is reshaping retail strategy as dramatically as the shift from brick-and-mortar to e-commerce, with 85% of retail executives now pursuing this shift.
  • →Non-negotiable personal practices (sleep, exercise, trusted confidants) are not wellness extras - they directly determine whether you show up for your team and customers effectively during surge moments.

In this episode

  1. 1From Startup Founder to Stripe CRO: A Colorful Career Journey
  2. 2Leadership Philosophy: Creating Followership Over Authority
  3. 3Navigating New Roles: Operating at the Edge of Your Stretch Zone
  4. 4Building Trust and Credibility Without Deep Domain Expertise
  5. 5Getting to Ground Truth: Talking to Customers and Frontline Leaders
  6. 6Preparing for the Hills: Sleep, Exercise, and Building Your Support Network
  7. 7Vision for AI at Stripe: Economic Infrastructure and Agentic Commerce
  8. 8Dartmouth Board Service and Giving Back to Alma Mater

Mentioned

StripeOpenAIAnthropicLiving SocialGreenhouseUrban EscapesCursorAura RingJohn CollisonGeorgeTiffanyDartmouth

Guests

Maia Josebachvili

Topics in this episode

StripeOpenAIAnthropicCursorAgentic commerceeconomic infrastructure for AILLM-driven shoppingground truthpost-it exercisedefault to trusthigh performanceC suiteexecutiveexecutive successionCEO coach

Questions this episode answers

How do you build credibility and trust when you move into a senior role where you don't have direct experience?

Josephbachvili creates a "phone a friend" list of 10 people she admires in that role and calls them to understand blind spots and what worked; she assembles an exceptional team with domain expertise; and she defaults to trust while maintaining humility and curiosity about what she doesn't know.

What is agentic commerce and why should retailers care about it now?

Agentic commerce is AI-driven shopping where customers use LLMs to help make purchase decisions; 25% of shoppers currently use LLMs for shopping and the number is rising rapidly, prompting 85% of retail executives to develop an agentic commerce strategy.

How does Stripe approach supporting AI companies with monetization and fraud?

Stripe frames itself as building economic infrastructure for AI, helping founders navigate global expansion, handle new fraud types, and solve monetization challenges - because the success of AI companies directly translates to Stripe's success.

What is the post-it exercise and how does it drive vision-aligned execution?

Team members write one idea per post-it note in response to prompts like 'what would make this a stellar year,' cluster them to find themes, and start from shared vision before debating execution - shifting the mindset from "why this won't work" to "this is our job, we'll figure it out."

What personal practices does Josephbachvili credit for handling high-pressure senior leadership roles?

She prioritizes non-negotiable sleep and exercise (tracking with an Oura ring), maintains a network of leaders she can vent to or seek advice from, and views these as essential training to handle the "surge moments" that inevitably come at senior levels.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

11 / 20

The episode contains several useful frameworks and leadership principles (default to trust, ground truth, the RAPID decision-making structure, post-it planning exercises) but substantial portions consist of throat-clearing, softball follow-ups, and general motivational language rather than novel, densely-packed insights. The host frequently affirms without pressing deeper, and Maia sometimes retreats into abstraction or familiar wisdom about 'great people' and 'having fun.'

Our job is to go do great things
you're not just handed authority and then you can tell everyone to do. It's actually quite the opposite. Our job so often is to talk to everybody, read all the things, and figure out where we should be going, and then paint a compelling vision that people actually want to go follow

Originality

10 / 20

While Maia articulates her views clearly, the core ideas - trust-based leadership, surrounding yourself with great people, customer obsession, clarity in decision-making - are well-established leadership principles circulating widely in the C-suite. The RAPID framework and post-it exercise are known methodologies. The skydiving pin-check anecdote is personal and engaging but doesn't translate to a fundamentally fresh insight about how to lead.

default to trust
surround yourself with great people, like both in caliber of talent and in quality of human

Guest Caliber

16 / 20

Maia is genuinely senior and relevant: CRO of AI at Stripe, 8-year tenure with multiple operating roles (GM of enterprise, head of strategy/ops, CMO at Greenhouse), founder/CEO experience, and board member at Dartmouth. She has executed at scale across product, sales, and emerging business areas. However, she is not a founder or CEO of a major public company, and the AI CRO role, while prestigious, is still relatively nascent, limiting the depth of proven track record in this specific function.

Chief Revenue Officer at Stripe. I've been there for eight years now
I was the GM of our enterprise business leading product and engineering

Specificity & Evidence

9 / 20

The episode lacks concrete data, named examples, and specific metrics. While Maia mentions 25% of people using LLMs for shopping and 85% of a conference audience working on agentic commerce, most claims remain high-level (e.g., 'we're helping customers navigate global expansion,' 'there's a lot of new gnarly types of fraud'). She references customers like Urban Outfitters and Etsy but doesn't detail actual outcomes, revenue impact, or specific problems solved. The anecdotes are personal but not quantified.

25% of people now are using LLMs for shopping
85% of people in the audience were working on some kind of agenda commerce strategy

Conversational Craft

9 / 20

The host Elizabeth is warm and affirming but rarely challenges or presses Maia on claims. Follow-ups are mostly validating ('I love that') rather than investigative. There are no instances where the host disagrees, asks a hard question about feasibility or trade-offs, or pushes back on vague statements. The conversation flows smoothly but remains largely at the surface level, with the host accepting Maia's framing without critical probing into execution details or hard choices.

I love that, the the more yes then no
I love it. Maya, that is like the perfect note for us to end on

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Most-used words

back22maya22stripe17team17leaders16help16love15executive14role14first13different10sure10customers10playbook9today9call9

Episode notes

In this episode of Executiveland, Elizabeth Freedman talks with Maia Josebachvili, Chief Revenue Officer for AI at Stripe, about what it really takes to lead at the frontier. Maia shares why authority is never handed to you and why the best leaders surround themselves with people who know more than they do. You’ll learn: Why leadership is about creating followership, not giving orders from a boardroom How to approach a role you have never done before by building the right network and team The "pin check" culture from skydiving and what it teaches us about defaulting to trust in high stakes situations Why getting to ground truth means talking to customers directly, not just reviewing data How a simple one page framework creates clarity in complex moments Maia also opens up about an early career mistake when she tried to act like what she thought a CMO should be, and why being yourself works better than fitting a mold. For more tools, insights, and strategies to lead with clarity and credibility, visit Elizabeth’s website , take the C-Suite Readiness Assessment , and

Full transcript

38 min

Transcribed and scored by The B2B Podcast Index.

Hi, and welcome to Executive Land. I'm Elizabeth Friedman, and this is where top leaders go off script to share straight talk and the unwritten playbook about life in the C-suite. For more ideas, visit East SuiteLeader.com.

Now let's dive into today's episode. Hi, everybody. Welcome back to another episode of Executive Land. And today I am thrilled because I know we are in for a fantastic conversation.

Now, she told me to call her Maya J, so I'm going to do that. But Maya, um, in just a minute, I'm going to let you introduce yourself. I, though, first want to introduce you as the chief revenue officer for AI at Stripe, which feels like an absolutely extraordinary role at an extraordinary time for AI. So you're going to tell us all about things AI at Stripe, but first, what did I miss from this introduction?

Probably lots. What else would you say? Well, first of all, thank you so much for having me. It's so great to talk about truly what is one of my favorite topics is just leadership and team building and you know how to get things done.

So yeah, today my role is Chief Revenue Officer at Stripe. I've been there for eight years now and have just been really lucky to have some incredible roles. So before this, I was the GM of our enterprise business leading product and engineering. And before that, I was in strategy operations.

I did MA. I was also our head of HR for a couple of years. So it's been a really colorful journey. And as were the chapters beforehand.

So just the very quick ones are, you know, I was one of the original team members of Greenhouse HR Tech Software and wore a bunch of hats there, including being CMO. Before that, I was founder and CEO of Urban Escapes, which is an e-commerce company I started and ended up selling out to Living Social and ran a few of the business units there. And I think the through line across all of those is I love jumping into the middle of what are the biggest opportunities and where are the best people working?

And where can you just kind of combine all of that to go make a huge impact and have a lot of fun along the way? You know, that's so interesting, Maya. I think even just where are the fun people, where are the great people, where are the best people working? It's such a good question to ask when you're exploring opportunities and when you're a talented person and have lots of choices.

I think that's the question. Well, okay, so Maya, I want to get into some of the different roles that you've played at Stripe and Elsewhere. But before we do, you know, one of the things we talk about on this podcast is it's it's executive land, right? This sort of, I don't know, place that exists, maybe only in our minds, but is the combination of these kind of unspoken behaviors or rules that happen at these senior leader levels.

And so you've been in some really pretty senior roles at Stripe. And so what happens in your perspective in executive land? Maybe what's good about it? What maybe don't they tell us in executive school that we should know?

Well, I might even reframe it. It's funny, we don't really talk or use the word executive. We talk about leaders at Stripe. And there's this image, I'm sure you've seen it, and lots of folks listening have seen it, where you have, you know, someone in the back telling people what to do, and then you have someone sort of in the front trotting the way and hoping and you know, leading people and doing things to help to create followership.

And I think one of the things about Stripe truly is that we really focus on creating leaders and developing leaders and celebrating leaders. And so I guess the thing they don't tell you, or I don't know, maybe they do tell you, is you're not just handed authority and then, and this is not just at Stripe, right? This is kind of all over. You're not just handed authority and said, okay, now you can tell everyone to do.

It's actually quite the opposite. Our job so often is to talk to everybody, read all the things, and figure out where we should be going, and then paint a compelling vision that people actually want to go follow. So if I had to sum it up, I'd say it is not, you know, the sort of what you used to see in movies is like the executive behind the big boardroom. It's actually much more just like being in there with everybody and making sure that we can all do it together.

You know, it's funny you mentioned the word executive, and maybe I'll link to it in the show notes because I've had lots of conversations about this word, which some folks honestly, it just sort of repels them. It definitely conjures up this very, I would say, old school, like unmodern vision of leaders. But, you know, I think I I've always approached it from that look, end of the day, it's about, you know, those individuals that, among other things, they are in a position to have to make decisions, let's say, on behalf of a part of the organization, even the organization.

And so if we look at it through that lens, Maya, so now I think about the different types of roles, even that you've played at Stripe. And how have you been able to accomplish this? Because not only have these have been different roles, to your point, no one's just saying, hey, congratulations, welcome to the job, what can we do for you? So, how do you how have you been able to, I think, so successfully get some very big things done and over the finish line, particularly when you've had to go from one role to maybe one that is quite different in nature in some in some ways.

Yeah, I love that you said no one just hands you the job and says, okay, what do you need? Right. You know, that has maybe for others. And I'd love to hear, you know, how they did it.

Yeah, me too. Right. But look, I'll just reflect on my own experience and journey. Again, I love jumping into where's the fire, where's the big opportunity, where can I have the most impact, and where can I work with amazing people?

And generally that's usually at the frontier, right? And so when you look back, like I said, I was in the enterprise role beforehand, it was really at a moment in time when Stripe was going from we were seven lines of code for the world's most ambitious startups. We still are that, but we also now serve 50% of the Fortune 100, and we have a huge enterprise business. I started that role right in the beginning of that.

And then as AI started really taking off, I also raised my hand and said, this is so important, and I want to be at the forefront helping to figure all this out. Now, you can look on LinkedIn and it just looks like this very nice linear path, right? Where like, oh, and then cool, great, big new job. To peel back the curtain a little bit, those moments are some of the scariest of my career.

And, you know, I always think about this concentric circles. You've got at the center of your comfort zone, and then you have your stretch zone, and then you have what I like to call the uh myologic curse. Can I say oh shit zone? Of course you can.

Of course you can. And then you have the oh shit zone. Yeah. And you know, the key is you really want to be operating at the edge of your stretch zone.

But I think often what happens, just to be really real, is it's hard to like always be there and you kind of jump into the oh shit zone a little bit and you're going back and forth. And so what do you do in those moments? For me, there's a couple of tactics that have just really, really helped. I think the first one is you need an amazing network around you.

You need sponsors who believe in you and have your back who you can go to and say, Hey, I'm stuck on this one. Can we talk it out? You need an external network. I like to call it the phone a friend.

You know, I've taken many new jobs in my career. And the first thing I do whenever I do any of them is I make the list of 10 people I admire most in that role. You know, I've never been a CRO, so I called some of my favorite CROs that I admire. And I go and I learn and I ask them, what did you do that worked well?

What should I think about? What are the blind spots? That really helps. So, anyway, that's all sort of, you know, around you.

The last and probably most important piece around you is you need an exceptional team. Because if you're not the expert in that field, you know, you bring a lot of other things. You better be sure that the people who you're working with are. And so, you know, now I'm so lucky.

I have this guy, George, on my team, who's just an exceptional sales leader and deep in AI. When I was leading HR for the first time, I had this woman, Tiffany, who was just, again, this incredible recruiter and people leader. And you just need to make sure all that is around you. And then the final thing I'd say is approach it all with tremendous humility and curiosity.

Wow, Maya. And I mean, you know, the idea of sort of being at the frontier and at the edge. Um, you know, again, back to this podcast is the unwritten playbook. Okay, there really is no playbook here.

There is no playbook. There is no playbook. And, you know, particularly walking into a role that, um, while you may be coming in at that senior level and and, you know, demonstrating all those elements you described, how does one really create sort of the trust, the credibility, the reputation in the news space? And how have you personally navigated that, Maya?

Because I certainly work with leaders where honestly they get a little judged. It's like, well, you haven't had 35 years of experience. So, you know, how have you earned the right to now direct our strategy or whatever the case may be? So how do you think about that?

I mean, I come across that too. I'm not immune to it. I I'll tell you an anecdote that has really shaped who I am. So, in a my early 20s when my prefrontal cortex was maybe not as developed as you know it is today, I was a very big skydiver.

Like I'm talking 750 skydives. Skydiver, people. I just want to underscore what Maya just said. In a couple of years.

Yeah. Wow. And I learned, I mean, I but I truly learned so much from that experience. And I'll describe one part of the skydiving culture that I just loved.

So to just explain this a little bit, the way jumping works is you know, you have your parachute inside. When you pull your parachute, it's not actually like a button, it's actually this little mini parachute that's connected to your main parachute, and you pull out the mini parachute, pulls out your big parachute. Okay. Okay.

And holding all this together is this little pin, truly one inch little pin holding it together. And what what you want to do right before you jump is it's really important to make sure this pin is situated very well because you know, you can imagine you do not want this pin coming out before you're writing for your parachute to come out, right? Right. Now, you can do your own pin check in the plane, but it's actually, you know, maybe 60% as effective as if someone does it for you because it's behind you.

And so what happens, and I remember just watching this and being like, wow, is you get on a plane, and it doesn't matter who's in that airplane, you could have never met them before. You get to 10,000 feet, it's about time to jump, and then everyone just like does pinchecks on each other. And if you can just picture this, these are people you've never met before, and you are trusting your life to them to make sure that everything is okay. And it is this culture where you just default to trust at the deepest levels, and that resonated so much with me.

And I bring that into how I operate every single day, and my team knows that. I default to trust, and that's not to say that you know you naively believe in everything, right? Like you can quickly get to the other side if you're not operating with integrity or not delivering. But I think I just exude this default to trust.

I try to surround myself with people like that. Not everyone is, and that's okay. But I really think building that culture from the beginning is probably one of the most important things to do. And the other thing I'd say is I I love the concept of the whole is greater than the sum of its parts.

I think magic happens when the team comes together. Right. And so look, the first six months are always kind of hard when you're starting a new job and doing something new. But you just have to know maybe, you know what?

Maybe there's a little bit of a playbook. The one playbook I'd say is surround yourself with great people, like both in caliber of talent and in quality of human. And I think Stripe just exudes that in spades. And you will figure things out.

I love it. You know, I'm imagining just that moment where the default to trust on the airplane before you jump. And, you know, although you didn't say this explicitly, Maya, I'm just picturing like, we gotta go. There's five seconds.

You know, you can't afford to waste a minute of energy on anything other than essentially the mission and trusting others. And I feel like probably, right, that that that same mindset here of, but that's a choice, Maya, right? Of really deciding. And I'm wondering what you've learned about that along the way.

So again, you've held really some incredible roles. You've gotten to be at the frontier at Stripe in different ways. Um, but maybe what do you know now about that experience? How has your thinking evolved?

Lessons learned along the way, given where you are now, particularly leading um AI. Yeah, you know, I credit John Collison a lot for really instilling this in me, but he always talked about get to ground truth. So when I was leading Corp Dev and we were looking at companies, whether it was to invest or buy, you know, you can look at their financials and you can talk to the leadership team as much as you want. You don't really know how good the product is until you've talked to 25 customers.

And that's what we talked about as ground truth. And so sometimes even before I would talk to the team, I would go and talk to 25 customers of that company and really try to find like what is ground truth. And that has stuck with me. And so, whether it's, you know, obviously MA is one aspect, but even now, as we think about partnering with these, you know, wildly ambitious AI companies, whether it's OpenAI or anthropic or cursor, we're always searching for ground truth.

And so I love talking to the frontline leaders and frontline team to talk about what they are seeing. I spend so much time talking to our customers all the time to just hear what's working well, but really importantly, where do your friction points? I need to know those. And so I think the best leaders I've observed are the ones who are able to play full stack.

They can do the leadership thing, they can do the vision, but you have to be able to get into the right level of details, you know, pick and choose where you do it and get to the ground truth. Yeah. Yeah. You know, I love that.

And to me, it's um related to that idea of where where are the challenges and the problems that we see and being able to just sort of see that in a way where either it's bringing that back into the organization so that we can, of course, address those. But I'm curious about that aspect, maybe, Maya, of your role. Because I was just talking to an organization and the analogy we were using was training for a marathon. And, you know, I think about I live here in Boston, Boston's got a big hill.

Hill training has to be part of the training. Yeah. Um, because inevitably we're gonna hit a hill. So, how do we train in the non-hill moments, if you will?

How do we just become that much better when challenges come up as they do? And I'd love to get your take on this because again, sometimes, right, we're gonna run into these issues, but how do we help each other so that when those moments come, it's not, you know, five alarm, fire, stress, chaos. We say stuff we don't mean, whatever the case may be. It's such a good question.

And everyone's on their own journey figuring this out. I'll give you my tips. I think one is I talked about the phone of friend before. It's just so helpful to have people you can call.

And sometimes it's actually to get deep advice. Sometimes you just need the safe space to vent. And I am so grateful for so many wonderful leaders at Stripe where I can do both with them because you need to put your own oxygen mask on first before you help others, right? So, like having those people who can also be your oxygen mask is one.

It's funny you talk about marathon training. I I think you know, this is a big part of my life. And I have found that a non-negotiable for me is sleep and exercise. And when you talk about training for those big things that will happen at work, I actually think it also means training yourself to be able to handle all of those.

And so I have learned over time that, you know, my aura ring is one of my favorite things. I've learned over time that I've got to get the sleep and I have to get the exercise in. Because if I don't, I'm gonna be a worse person than a worse version of myself. And I'm not gonna show up for my team and the people around me and our customers in a way that they need me to.

Yeah. So, you know, is it? I don't know if it's training for the fire, so much as it is like training yourself to be able and having the system around you to handle when stuff hits the van. But I do think you really need to always be preparing for those surge moments because they will happen all the time.

Absolutely. And, you know, you think about the more senior you get, and depending on the part of the organization or business you're running, those hills can have quite a quite an incline, right? And so all of the things we do on a regular basis to sort of prepare and practice for those moments, if you will, Myer, be ready for them. I'm curious, from your vantage point, if there are other kind of natural areas we would look to to almost know either these are the things to proactively intentionally consider so we're ready, or that we want to be developing in ourselves and in others.

And I'll give you just one example that comes up a lot in the work I do because we're talking about very senior leaders in big roles. One of the things I noticed that they do so well is I'll say a little more yes than no. Yes, meaning, how could this work? How might we try if we were to do this?

And half the time, how could we? Counter to that is the here's why that won't work, Maya. We've tried that before, you know, that kind of energy. And so I see that ability to be a little more yes and no is maybe one example of, hey, that's gonna be one of those behaviors that's really gonna help us when those hills come.

But I'd love to get your take on that. I love that, the the more yes then no. And I think it actually, again, goes back to the people. Yeah.

If you have the people who can do it and who and you believe in them to do it, they will move mountains for you. One of my favorite exercises to do whenever it's either forming a new team or going into planning, is you get everybody around the table. And I call it the post-it exercise. I mean, I literally have post-its everywhere.

And and the prompts can be a little bit different, right? Let's say you're going into yearly planning. I say, okay, what do we want to be able to say at the end of next year? Like what would make us say this was a stellar year?

Or you could do it, you know, if it's a project and you're kind of trying to figure out all the options, and everyone writes one thing for each idea you have, it goes on the post-it note. And you know, you have quiet time up front. And then you all take turns going up to the whiteboard and putting your post-its up, and you end up clustering them because you see those different themes. And to me, that is just creating the space and the energy to dream really, really big.

And so it even takes it one step back from how you were talking about it. Like, it's not even about like, will this work or not? You start with like, where do we want to be? Okay, and then we figure out how to get there, right?

Because if that's what we all agree is our vision, then we will figure it out because that's our job. Our job is to go do great things. Agreed. Absolutely.

And so, hey Maya, I mean, only blame yourself for this question because I want to know what would be on the Maya post-it notes. And so curious how you're thinking about this. You're in this incredible role, big, big vision plans for all things AI. So it's a year from now.

What would make this a stellar year for Stripe, for you? What have you and the team been talking about? Yeah, it is such an incredible, exciting time out there. I am just in awe and admire what all of these AI founders are working on on one side of it.

And then also what all these large brands and retailers are doing to completely reimagine how they do things in this new age of AI. And I'm so lucky that I get to. Work with both of those groups of people. Yes.

I view we're building Stripe is building economic infrastructure for AI. Our job is to help them all thrive in this new era. So the AI company's success is our success, and the Fortune 100 company's success is our success, and the millions of other customers we have. When they succeed, we succeed.

So when I look at what a great year looks like for us, all these AI companies are really trying to grow and to navigate the global expansion. There's a lot of new gnarly types of fraud that they're hitting. Monetization has completely evolved. Like how you price for AI is so different than how you used to price for, you know, standard SaaS subscriptions.

We're here to help them figure that out. And so to me, success is that we've helped all of our wonderful customers succeed in their worlds. And then on the flip side, you know, I'll give one example, but agenda commerce has really turned retail on its head. It's 25% of people now are using LLMs for shopping, and that number's going up so fast.

Just I was at a big retail conference recently speaking, and we asked who is working on an agenda commerce strategy here in the audience. We had a thousand people in the audience. And we did like the the um the voting thing. 85% of people in the audience were working on some kind of agenda commerce strategy.

Wow. But this is like a shift from brick and mortar to e-commerce, from websites to mobile. I mean, honestly, it's probably even a bigger shift than that. And so, how do we help all of these brands and companies like urban outfitters and free people, anthropology, Etsy?

We're talking to all these guys and trying to help them navigate. Well, we're all navigating. How do we do this successfully? I mean, it's incredible.

Well, so we'll have you back on the podcast, you know, and hear all about how you and the team at Stripe, of course, accomplished this, Maya. Um, I know you're also doing this though in any number of other forms, including Dartmouth at the Incredible School, your alma mater, and of course, you're you're on the board of trustees at Dartmouth. And so want to talk to you about that maybe in two ways. And of course, we want to understand a little bit about just kind of what is the role you're playing there.

But also, Maya, I think it's just the ways in which you've approached your career, that you've really thought about how do you be part of these wonderful sort of opportunities and environments with great people. And I really believe people are listening thinking, how do I do that? And so maybe talk to us about sort of how you think about that. And maybe I'm gonna say my is my secrets to career success.

I don't know if I would call it success, but I'm having fun. I will say that. So the Dartmouth experience has been just like one of the most humbling and rewarding experiences that I've ever had, truly. It's an institution I care so deeply about, and to be able to give back in such a profound way means the world to me.

We have this unbelievable precedent. I mean, you want to talk leadership? See on Bilock is really paving the way for I think how higher education needs to evolve. And in many ways, my job as a trustee is to help support her vision and make sure Dartmouth is set up, you know, it's a it's an enduring 200-plus year institution.

What do the next 200 years look like and how do we think about that? And one of the questions we're really grappling with is how does higher education need to evolve right now, especially in the AI era? I mean, there's so many other things, but from my vantage point, I'll talk about AI. AI is redefining what work looks like.

You can just take the role of a software engineer. It is unrecognizable today than what it was a year and a half ago. And that's just one role, right? Like you wouldn't dare dream of coding without a Claude Code today.

I'm vibe coding apps with my seven and eight-year-old right now. Wow. It's it's just night and day. And so then the question that really poses is well, like, how does higher education need to evolve for this for this new era?

And the thing that we keep coming back to is, you know, Dartmouth's secret sauce, Dartmouth's focus is really on preparing the next generation of leaders and teaching people how to think, not what to think. This is, you know, Sion's so great at this. I think that's more important than ever in the age of AI because you have every answer at your fingertips today, right? So, and and arguably higher ed was never just about knowledge transfer, but it's certainly not today when knowledge is everywhere.

And so, one thing we've been talking a lot about is what do great leaders do and exhibit? They can have the uncomfortable conversations. They're adaptable, they're continuously learning. They're the ones who are picking up the new tools, they're the ones who have empathy and great collaboration and communication skills.

Like those are the things that make great leaders. And so it's been really fun to be on the journey with Sion and the rest of the board and the amazing faculty on how do we help continue to cultivate that in this next generation because it's more important than ever. You know, I love that, Maya. And I think that idea of how we can help people think, right?

What does that look like? And I tend to operate on the other end. What does how does that translate to the senior leader population? And maybe an example that we already discussed, that kind of it's more yes than no.

It's the there is no playbook because so much of this is frontier and new. Um at that senior level, that you know, really we're running companies, we're running divisions, what else has changed? And even if I go back to when you joined Stripe in 2018 to now, more from the how we need to think, yeah. What else has evolved in your view?

One thing I'm really leaning into is what is the life cycle of product development look like? And what does you know the buzzword of prod go-to-market interlock mean? And again, I just feel so lucky. I work with this incredible partner on the product engineering side, Kevin.

And something he and I are really working through is how do we bring these ideas to life now and bring them to our customers? So you think olden days, product and engine builds the thing, obviously in collaboration with user feedback, but you build it, you put it through new product introduction, whatever your process is, and then the sale field goes sells it. Things are moving so fast, you don't have those cycles anymore. It all needs to be one fluid thing.

And so, so much of what we're doing is we just it feels like one team. We act as one team, you know, with product, engineering, marketing, sales, our solutions architects, and we're and our customers, by the way. And so we are actively building at the same time that we're working with our customers, you know, we always do the the playbook that we're starting to build right now that I really like is we align on our first 10 hero users who are the design partners who will give us the best feedback, and we work with them really closely.

And it's all of us together feeding back the feedback to help iterate and build what they really need. So I think that's like actually a pretty fundamental structural shift in how companies are evolving and building products and helping their customers be successful. You know, it really goes back to sort of where we started the conversation. It is not an executive sequestered away in an office, I don't know, cooking up ideas and like barking out orders.

True integration. And I mean, what you're describing to me is just a whole different level of how we actually have to partner and collaborate, listen, be curious, right? Ask those questions. Um what else has evolved, if anything, that you're seeing, Maya?

Because I think we want to help people understand sort of what does it mean to be? I'll call it the modern executive. I'll be vulnerable here. So, you know, I mentioned I was one of the early folks, first employee at Greenhouse.

I had started as VP of Strategy and VP of people in that role. And at one point we had a leadership transition, and our CEO and the board said, you know, you've been doing so much of the marketing work already. Why don't you come and step in as at the time it was interim CMO, ended up staying as CMO? And this is arguably one of the first times I had jumped at a larger company and jumped into a role that I had never done before.

Now, it felt great, and again, back to sponsors, it felt great to have the boards backing and my CEOs backing. You know who didn't have my back or didn't believe in it is most of the company. And why would they, right? I had not been in marketing before, and they weren't in the back room having the conversations and seeing, you know, what I was doing on the marketing front.

And so there was a lot of pushback about whether I was the right person. What did I do? Well, I was like, all right, well, what do CMOs do? They wear, and this is very outdated now.

I was like, well, they wear pencil skirts and good heels, and they're usually, you know, dressed to the nines. Of course, of course they do. I like completely changed my wardrobe and started, you know, acting the part of what I thought was a CMO. And how do you think that went?

Completely backfired. It got worse, right? They were like, really? Now she's trying too hard.

And it was just a tremendous lesson in you can't be, or you can't try to be what you think others think you should be, and try to fit some mold. You just go back to all the things I was saying before is build a great team around you, get to ground truth, really focus on your end customer, and just get through the muck, and then it'll work. And you know, the the end of the story is really wonderful. I ended up having a wonderful couple of years doing that, built an incredible team, and I think we really made a dent in that world.

But it was really a great first lesson in just stick to what you know. And some things never got a style, like be customer obsessed, work with wonderful people, really focus on where you're trying to go and what's the vision. And those things will always, always keep working. Well, Maya, listen, you know, again, we talk about how to be successful and navigate at these senior levels.

And before we go, I'd love to get some guidance from you. Picture those listening that want to be able to influence someone like you, that maybe report to someone like you. And you've talked about how you give trust first. But what are some other things that you have noticed that work well and maybe that erode trust, whether we're talking about you or that you've you've seen in a broader way?

A leader's job is to create clarity and context for people and make a couple of very high-stakes decisions. And so the best thing you can do to support your leaders, and I think about this with you know, Patrick and John and Will and Tyler and Eileen and the leaders I support is how do I help create the most clarity for them so that I can be one input in their, you know, whole map of what they're trying to create clarity with. And so what I really value when folks bring to me is just whether it's some gnarly situation or some decision that has to be made, did you lay it out as clearly as possible and with the context you need?

And so I'll just give like a really simple framework I really like. Oftentimes, when you're stuck in these really tough situations that you have to make a decision on, there is no right to answer. And and it's certainly not obvious because if it was obvious, it wouldn't have, you know, bubbled all the way up. What it really means is there's a couple of options and there's some pros and cons, and we need to be really thoughtful about which downsides are we willing to take and are there mitigations we could do.

And so I love like a really simple one pager that has at the top here's the situation, here's what's happening, here's the simple context, and and I'm gonna be very tactical here, but like bullets over paragraphs. And the reason I say that is in a paragraph, you can kind of you know get a little long-winded. If it's a bullet, it's like each sentence needs to state something very helpful for you to understand. So you set the context up front, and then you say, get very clear.

Here's the decision we need. In one sentence, what is the actual decision? Who are the decision makers? This is actually one of my favorite questions to ask is who's the decider?

And so often it's unclear in that the swirl is actually less like what should we do? But it's like it down. That's true. And so we actually I helped institute a straight um what we call rapid, and any framework is fine.

The point is you put down who's the D and who needs to agree, who's the A. And then you say, here's our three options, or two or four, and here's the pros and cons to each of them. And all of a sudden, you've just framed out this very complex situation in one page, and it's still a hard decision to make, but at least now you're clear. What do I need to know?

What decision do we have to make? Who's the decider? And what are the pros and cons to the three different options we have? And that to me is just a very simplistic but very clarifying way to help move organizations forward.

You know, I want, I mean, we got to record and like play that back again and again, Maya, because I'll tell you when you talk about how do we create that context and clarity, but also how do we help others think in this day and age? I mean, you've just given us, I think, just such a beautiful way to do that. And so, Maya, on that note, we will say this before we go, anything else that you want to make sure people know about what life is like, I'll call in executive land. What did we leave out of the conversation that we also want to make sure to underscore before we wrap up?

I think we touched on all of it. Look, if I had to boil it down to one thing, it's it's being a leader is hard. We all know that. So if you're going to do it, make sure you're working on important problems that you care about with people that you respect and you admire and you learn from and you have fun with.

If you can nail those, you can get through the tough parts. So that that's my guiding light always. I love it. Maya, that is like the perfect note for us to end on.

Thank you. And uh, we'll have you back. Good luck with the posted notes, and we can't wait to talk to you next time. Thank you.

Thanks, Elizabeth. It was so great. Well, that's all for today in Executive Land. Thanks for listening.

And if you're looking for more, check out my website, eSuiteLeader.com, where you'll see all kinds of free resources and take the free executive readiness assessment. It shows you exactly where you're strong and where to focus next in your own leadership. And don't forget, subscribe to this podcast so you never miss an episode.

I'll see you next time in Executive Plan.

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