From Burnout to Balance: How a Former CEO/CPO Built a Thriving Portfolio Career After Corporate Exhaustion, With Kristin Chen

What was your path into product management?

My journey into product management takes me back to LinkedIn, my first tech job. Prior to that, I worked at Franklin Templeton Investments doing economic research before transitioning to tech to work on data and analytics.

At LinkedIn, I was on the insights team where half our time was spent working with LinkedIn's largest clients and top sales teams, creating narratives about leveraging LinkedIn's data for hiring, sales, marketing, or learning. The other part of my job involved building internal tools for sales teams using our data.

I built some very popular internal tools—one called the relationship mapping tool and another called Decision Maker. When these had internal success, we'd work with the product team to implement them into Sales Navigator or the Talent Insights product. That's when I realized, "Hey, I'm good at this, and it's fun. I want to be the one scaling these products."

I gave myself about six months to one year to transition. I talked to all the product managers I knew at LinkedIn and outside LinkedIn, plus cross-functional partners. I asked about the best and worst PMs they worked with because I truly didn't know what product was and wanted to make sure it was the right fit.

I started interviewing and got rejected from many places. I failed a lot of interviews but got better each time. Some people told me I'd never make the transition, but others were encouraging. My mentor at LinkedIn, Nitin Julka, said my data analytics background was close enough to product—you need to be data-driven.

Six months into my journey, a friend referred me to Twitch. There happened to be a role in the developer experience team needing someone to build insights products. Ironically, I had been frustrated thinking my insights background was holding me back, but it's what helped me get the role. I joined Twitch as a senior product manager because of my expertise in the insights function.

Later, I moved to Pinterest from 2019 to 2020 to help build out the foundation for the creator platform. I worked at the intersection of how Pinners could interact with creators—launching reactions, owning the following feed, creator recommendations, comments, tries, and also building creator tools.

What made you want to transition from climbing the corporate ladder to owning your own path?

Transparently, I'm a big workaholic. My managers always said I was pushing myself toward burnout, but I was stubborn. After back-to-back roles as CEO at TopGG and CPO at MetaTheory, I'd never worked so hard or so many hours in my life. It was a high-pressure environment—exciting, building, shipping—but I was truly burnt out.

I realized my leadership style wasn't matching with the rest of the executive team at my last startup. I was also the only female executive as a CPO, which was difficult in the combined Web3 and gaming industries. I also realized that while I loved games, adding the money aspect of Web3 took the fun out of gaming for me. I just wasn't super passionate about the space.

Separately, my mom was going through a major health challenge—a tumor the size of a tennis ball in her pancreas. While that wasn't the main reason I left, it woke me up. I realized I wasn't present with my family. I was always checking Slack, even on vacation. I wasn't happy and had lost my passion for the problem space.

Initially, I thought I'd take 2-3 years off and do nothing, but I started going crazy and felt extreme guilt (immigrant parents—"How can you not work? What is vacation?"). Then organically, after posting on LinkedIn that I'd left, I started getting inbound requests. When I told people I couldn't work full-time, founders said, "We'd still love to work with you in any capacity. How about as a product advisor? How about fractional?"

So I fell into it for the first six months. My sister, a designer, made me a website on Squarespace despite my resistance and imposter syndrome. I'd always had inbound for career coaching since I used to work at Cornell's Career Services and at LinkedIn. In October 2023, I posted about my services on LinkedIn, Twitter, and Instagram as an experiment, and now it's been almost two years.

What does a typical day look like for you as a startup advisor/fractional CPO and coach?

My days vary greatly! I balance a bucket of clients where I'm either doing startup advising work or more hands-on fractional CPO work, typically with pre-seed to Series A startups. This involves working directly with founders and team members on anything a CPO would do.

This could include helping with fundraising decks, preparing for board meetings, conducting hands-on user research, giving feedback on product strategy, designing hiring processes, facilitating offsites, prioritizing roadmaps—literally anything a CPO would do.

I also balance executive coaching with clients from various career levels—from high school students to CEO/CPO level executives—and across functions like design, analytics, operations, marketing, and engineering. This might involve helping with active negotiation, deciding between offers, beginning a job search journey, professional brand makeovers, interview preparation, or developing elevator pitches.

The fun part is owning my time and schedule. My goal has been not to work full-time and to carve out time for my health. Yesterday, for example, I had a morning meeting with a career coaching client, went to my aerial yoga class, had lunch with a friend at Google, then came back and did more work for one of the startups.

The challenge is definitely the context switching—as a PM there's already a lot, but now there's even more!

What have you had to learn v.s. unlearn in this journey?

The biggest challenge is being more arm's length now. As a CPO, CEO, or director of product, I led teams with direct reports. Now I'm more of a coach and mentor to the founder and team members. I've had to learn where I can add the most impact and leverage since I'm not working with them full-time.

I had to unlearn being "all in." I was used to living and breathing one company 24/7, always checking Slack. Now I have different clients and need to determine where I can add the most value. I couldn't have the same anxiety about being all-in as before—it wasn't healthy for this new phase of my portfolio career.

Negotiation is different too. With each new client, I need to align upfront on exactly what I'll do, how many hours we'll devote, and what the engagement looks like. The legal aspects, taxes, and accounting were all new to me—just part of being a small business owner.

I also discovered that my relationship with each CEO is different. Some say, "I trust you, do whatever you want, imagine the team is reporting to you," while others need me to run things by them. Finding the right fit with each founder and their style is crucial.

Bonus Question: What's your favorite clothing brand?

For athleisure and athletic wear, I love VUORI—the fabrics are amazing! They also have an outlet in Livermore that I wish I'd known about sooner. I also love prAna.

For other clothes, I love Staud. They have great pieces that are borderline business casual, vacation wear, or what I'd call "creative corporate"—professional but not too corporate, a bit edgy but not extreme. I always get compliments on their pieces. Frame is another brand I love for denim and other clothing.

With style and fashion, I've been able to take more risks because places like Pinterest, gaming, and Web3 companies are more fashion-forward and casual compared to when I worked in finance wearing Theory suits. Now, working for myself, I can be more fun with my style or match what the client expects.

Spicy Question: Do you feel like the fractional executive path is only for people who have financially "made it"? Or is it viable for people still climbing career ladders?

I believe anyone can do this with the right mindset and work, but you need risk tolerance. It's very different working for yourself versus having a steady paycheck, insurance, and 401k matching. I pay for my own health insurance now, which made me appreciate the benefits and stability of corporate life.

It depends on where you are in your career, how much risk you're willing to take, and if you're ready to put yourself out there and invest in your personal brand. If you're going to quit your job to do this, yes, you should have financial stability. I had saved enough to not work for a couple of years and wasn't expecting to immediately replace my CPO salary.

Some people come in with that expectation, but that's likely not what will happen. When you go off on your own, it takes time to build up, find product-market fit, figure out your offerings and pricing. I only started feeling comfortable a year in.

For those earlier in their careers, I've seen people offer consulting or create mini agencies. The tricky part is making sure your employer is okay with it if you're not fully leaving. I've seen horror stories where people took on advisory roles without reporting them and got fired when the company found out.

Having financial stability helps because you won't have consistent cash flow. You need a bigger emergency fund, especially if you're supporting a family or have a mortgage. I always encourage people to run an experiment first—test out advising before fully committing to see if you like the context switching and client work.

Investing in your professional brand is crucial. Many of my clients came from talks I've given, podcasts I've been on, or networking. I still get inquiries from a podcast I did with Chloe Shih several years ago! Don't be afraid to put yourself out there—you can't get to the top without some haters, but so many more people will celebrate and support you.