Career Design, Resilience & the Run Your Race Philosophy

All right, Indy, I'm super excited to have you on this show. I was just looking at your LinkedIn profile again, and honestly, on paper, it looks like the dream career for anyone — not just the logos you've accumulated, but the places you worked in the world, the roles you had at different inflection points, joining companies at high-growth stage, pre-IPO, going to IPO. You've done it all. So the first question I want to ask, going straight into it, is: on paper it looks amazing. In real life, how was the experience? Has it been as fulfilling as it looks on paper?

Yeah, I love that you're starting with that question. I would say — what is that answer? — it's complicated, right? I think on paper, and this is true for so many people, everybody is on the up and to the right, logo after logo, the whole trajectory. And I think you owe it to yourself from a career standpoint to be very purposeful and design your career. There's no doubt that some of the moves I made were based on whatever plan I had at the time to keep learning and growing. I made a couple of transitions — I was a management consultant out of college, went to business school, then wanted to get into marketing. In marketing I had the opportunity to work at big companies, startups, scaleups, and each time it was with different learning objectives or professional goals in mind.

To answer your question — so many of us feel like our careers look like a straight line up and to the right, but it's anything but. It's very curvy, there are ups and downs. So to answer the second part of your question: no doubt there have been some bumps along the road. You learn both from your successes and your failures. There are a lot of things that peppered my experience at both levels — success and failures — and you learn from them. You course correct, you adjust.

At the end of the day, I always go back to this notion that your career only belongs to you. If you don't make the right choices or take the right learnings at some point in time, you might wake up one day and realize you're well along a path you never intended to be on. I've always thought about my career as something I want to actively direct — not just be a participant in, but design myself. A lot of people look at folks like us on a piece of paper and it seems like it's on the up and to the right and straight and narrow — but it obviously has its bumps and ups and downs.

What have been your most exciting personal growth experiences? When I look through the list — Salesforce, Box, MuleSoft, Google, WeWork, Matterport, Canva — it just keeps going. Where have you learned the most, in these different roles? Whether it was the type of company, the role, the stage you joined — where did you grow the most and why?

For me, I think it comes down to a couple of areas. Every place you go, you learn and pick something up. But if I were to think about the things I learned as a marketer — I think about our craft a lot in marketing. No doubt, Salesforce was a great place to start my journey as a product marketer because I can count on my hand the number of companies where product marketing really has the juice and the ability to shape the narrative. Salesforce, bar none — outside of maybe Apple — is one of those companies where product marketing comes in with a strong view and leads both the messaging and the narrative in the market. I feel very lucky to have started my marketing career there. That's on craft.

I have this three-dimensional filter that I look at when thinking about different companies and experiences. The first filter is product. The second is culture. The third is execution. Salesforce — I talked about craft — that's execution. On the product level, most recently Canva has stood out in my mind as a product company where the product is so darn good. They're obviously evolving a lot with everything happening with agentic AI, and I think they're navigating that very gracefully. But at the end of the day, your product is your calling card in the software business. If you don't have a great product, there's no amount of marketing that's going to mask those gaps down the road. Having that ethos for what makes a good product and a good first-time user experience — that's something I've learned is super important, because your marketing, your narrative is only going to be as good as the product itself.

Culturally, I've learned a lot from all the companies I've been at. Without naming names, there are some companies that from the outside looking in seem like they have great cultures — that's not always the case. When you define culture, what I've learned both as an early employee and as a leader is that you can have all the mission statements in the world, all the ping pong tables, all the kombucha on tap — but culture has to match something deeper.

I think of messaging as the outward facing piece, and brand as the promise you make to your customers — it has to be consistent no matter what. The best brands do that: Apple, Coca-Cola, Nike. Culture is the other side of that coin. Culture in my mind is the promise you make to your employees, your collaborators, your partners. Saying: what you see from us is always what you're going to get. There are going to be ups and downs, wartime and peacetime, but culture is like the internal brand and the promise you're making to your employees. I've seen companies where everyone thinks they have a great culture and they don't, and companies where people think it seems boring but the culture is awesome — and that's sometimes what keeps you there.

What are the moments that were the most difficult for you? Because on paper you don't see the struggles, the challenges, the pivots. What are the biggest challenges you've had to deal with behind the scenes, and how did you pivot out of that?

I think of a few. Maybe I'll give you two examples — one on the professional side and another that hits closer to home, but the lessons are equally valid. On the professional front: 2019. I like to call it the year of the Lord. That's when I joined WeWork, which was on a complete tear. For those who may not remember, WeWork was on an absolute meteoric rise, poised to go public. And then almost overnight, investor sentiment soured on the company. We filed our S1. Unfortunately, for many reasons, it was not super well-received. A lot of that fell on us, and a lot of it was people realizing that there was so much money being thrown into this category and asking whether the business was really as viable as it seemed.

There were many things above my pay grade that I had no control over. But overnight I had people I had to let know their jobs were going to be vacated — we were literally running out of money to pay people, so the company had to structure massive layoffs. My CMO and I were across those motions and had to make really tough decisions. And then eventually those decisions were made on our behalf — both my CMO and I were part of a massive layoff of around 3,500 people, a lot of them from the Bay Area who had left really amazing jobs to join this rocket ship.

At the end of the day, I don't regret that episode. You often learn more from your failures than your successes. I don't know that I would do anything really differently. What it did teach me is that it's all about the grace with which you navigate those things. A lot of people were rightfully upset about what happened. For me, I hadn't been there long enough to have equity — I didn't have any at the end of the day because I hadn't made it past the whole year. But there were some people who had already made very important financial decisions based on what they thought the outcome would look like.

What I learned is: one, as a professional, never think of a high-flying startup as a meal ticket. If anything, the equity is a lottery ticket. And two, you can't take these things personally. It's not your fault that maybe the company goes belly up. I think what I realized — and it took some of my close collaborators a little while to absorb this — is that your job is not your identity. It's so tempting, and Silicon Valley and the tech sector are so guilty of this: they give you a T-shirt, stickers, you're part of the family, you're part of the winning team — until you're not. I should never tie my identity to my job. Think about careers as "what's the dream work I'm going to do?" as opposed to "what's the dream company and the dream job?" Because titles and companies go. But if you can keep your head high on the craft — what you've done, the accomplishments — those speak for themselves.

One of the things I did when I knew things were going south — I had a team of 30 people, eight or nine direct reports — I had a leadership training while the ship was going down. I told them: there's a lot of ambiguity right now, but I want to help you make the right decisions for your career. If you want a recommendation and are looking for another job right now, do it. I'm not going to hold it personally against you. I'm here to support you. I want you to manage your energy. In times like this, people thrash — the negative energy consumes them. I've learned as a professional that you need to manage both the charge of your energy — positive versus negative — and the amount you have. If you're dealing with negative energy and low energy, you're going to burn out.

The last thing — and this hits home — is that life also happens around you. You can never take your health for granted. I lost my father in 2017. He had a great life, he was getting there in terms of age. People grieve in different ways. My brother grieved immediately. For me it took a little bit longer to hit home. And in many ways that affected how I thought about my career from that point on. I realized very quickly that life is short, and at least you want to live life on your own terms. I think that's probably what led me to the path I'm experimenting with now — this fractional advisory type of work — where I felt I owed it to myself to take some more risks. About a year after my father passed away, I left the creature comforts of Google for WeWork. I was thinking that was the right move at the time — and it was. I don't regret it. But sometimes, both professionally and personally, things are going to happen to you that will affect how you choose to live your life or your career after that. What doesn't kill you makes you stronger. And sometimes it forces you to focus even more than before.

What advice do you have for founders in this age of AI where everyone's shipping something, it's getting very noisy, there's a lot of talk about the end of B2B SaaS and everything else? What advice do you have for people who are looking to launch their business, their startup, their impact in the world, navigating through this very innovative and transformative time?

I would go back to what I've learned about running. My motto is: run your race. I think it's applicable to both your personal life and your professional life. At the end of the day, all these entrepreneurs, all of us as business people — our careers are going to evolve and our success is going to look and feel very different from person to person. In a marathon, I'm not going to be the first one to finish and I'm not going to be the last one — but I'm still crossing the same finish line on my terms.

The advice I'd have for founders navigating this era is that there's just so much noise and commotion around you. It's very tempting. FOMO's never been bigger than it is right now. People are saying, "Anthropic is launching five features every day — I need to do that too." I don't know that you need to do that. As long as you keep your focus on what you're doing and can be deliberate but incremental in building what you want your business and product to look and feel like — speed is obviously of the essence, but don't rush into the market and try to copy something you're doing out of a trend or FUD or FOMO. Sometimes I'll be running and I see somebody who looks way older than me and is much faster, and I think: they're built different and I'm built different. I'm going to honor my own pace and what I want to do, because at the end of the day I have a goal, and if I can execute on my plan and get to where I am, nobody's going to take that away from me.

Comparison is a thief of joy. Focus is going to help you nail what you need to do and know how you're going to do it. Don't succumb to FOMO. Believe in your conviction. Solve the problem that fascinates you as opposed to the problem you think the market wants. If you do something that fascinates you, there's a very high chance you're the only one as passionate about it as anybody else — and that fascination and passion is going to show in your work. Don't go too slow, don't go too fast. Be purposeful in what you're doing. That's how I approach my marathon training. That's how I approach my work. Over time I've seen that pay off. It also helps with not getting ahead of yourself, not burning out. And then on the other hand, it leads to more purposeful and impactful work.

What immediately resonated for me about Full Stack CEO — other than the chance to work again with you — was what you said about managing your energy. All these incubators and associations are always about "go go go, hustle harder." The orientation you have around saying that entrepreneurship is also like a sport — you're building a team, you're at the wheel, and the energy you have is the energy you give — that coach mentality is going to be really important. I really believe you can only do your best work if you manage that energy and are in the right frame of mind.

It makes zero sense to me that I spend more time charging my iPhone than I think about when I should go to bed. I always try to balance what's giving me energy and how I replenish it to make sure I can go back to my craft and give 110%. As a runner, I'm seeing more and more that what I've learned from running is mirroring how I want to show up professionally.

Throughout my work I've been lucky to be working on products and initiatives that always had a component where I'd end up speaking to tons of entrepreneurs and startups. At Salesforce on the ground floor of the AppExchange, the companies who wanted to build on my platform were sometimes tiny one- or two-person startups. I always had an affinity for working with those communities, because what I really derive satisfaction from is being able to help steer pieces of a company's strategy, their go-to-market approach, and be a multiplier. When those companies found product-market fit, they took off. That has been a through line of my career — whenever you can work on a business where your function exists to have a multiplier effect on others, that's always something I've been super energized about.

If you want to reach me, there are two ways. One is through the Full Stack CEO channels. I also have my own newsletter called The Remarketables — I'm revisiting some of the greatest marketing launches in modern history and deconstructing the playbooks behind them. It's almost like a passion project, but it makes sense in what I want to do. The inspiration comes from podcasts like Acquired — but as a practitioner who's now spent 20 years in marketing, I have the headspace to look back on some of these things I've admired from afar and think about what must have gone through the minds of the people who executed them. And then you can also find me on LinkedIn, or at indysen.com.