I’m joining Chief!

Leah Fessler
chief.com // check it out

I am **extremely** excited to announce that I am joining Chief, based in New York, where I will be leading editorial and brand voice. Chief is a tremendously badass company, led by women I’ve long-admired, Lindsay Kaplan and Carolyn Childers. Their mission is to create the first and most-powerful professional network of women in C-suite and VP-level roles across industries. Chief recently raised $22 million co-led by General Catalyst’s Ken Chenault, the legendary former CEO of AmEx, and Inspired Capital’s Alexa von Tobel (both Ken and Alexa now hold Chief board seats).

Every career decision I’ve made is highly intentional. If I’ve been lucky enough to know you, learn from you, or engage with you as a writer, I believe I owe it to you to explain the logic behind this jump from VC and journalism to an operator role at a 🚀 (yep, that’s a flex).

Or maybe I just needed to write this out for myself. Either way, here goes it (sorry this isn’t short!):


People often ask me what, exactly, I do. It’s a good question. I don’t really know the answer.

After studying English and creative writing at Middlebury (and raging against the finance and consulting machine), it confused many of my peers when I decided to start my career in management at Bridgewater Associates, the world’s largest hedge fund.

I still resent working in financial services (some biases die hard), but culture drove me to Bridgewater. I am obsessed with truth, logic, open-minded debate, and relationships rooted in vulnerability and trust. I’m obsessed with working with smart, diverse people who challenge me to see my blindspots, explore my weaknesses, and amplify my strengths.

Bridgewater checked all these boxes. It also financially supported my future in a way other post-grad options never could have. The importance of this nest egg cannot, and should not, be understated.

Bridgewater was worth it. Making a lot of money, even if you’re not totally thrilled every minute of the day, was worth it. Crying in front of a room of strangers almost monthly was worth it.

Working at Bridgewater gave me the confidence and stability to pursue journalism, which was my life-long dream. Writing explicitly and honestly about issues others were unwilling to unpack (namely women’s experiences with hookup culture and lack of sexual pleasure) landed me a staff reporting job at Quartz. Similar to Bridgewater, I joined Quartz because of culture and growth opportunities. Then a startup (Quartz launched in 2012, and was owned by by Atlantic Media until it was acquired by Uzabase last summer), Quartz was a collective of brilliant, nerdy humans obsessed with high-quality writing, weird framings, and reimagining the future of digital media.

At Quartz, female mentors and editors (Sarah Todd, Georgia Frances King, Lauren Brown, Heather Landy, Indrani Sen, just to name a few) spotted my raw talent, excessive drive, and obsession with infusing more feminism in Quartz’s coverage. They took countless risks on me, giving me a long-leash to report on anything from the gender biases embedded in Siri and Alexa (a report that went on to influence Apple and Amazon’s reprogramming their assistants), to gender influences Slack communication, to re-writing Louis CK’s apology letter, forcing my colleagues to write “user manuals,” unpacking loud chewers at work, and promoting the correlation between powerful women and dogs.

Quartz women epitomized strong leadership, mentorship, sponsorship, and empathy. They loved me by pushing me to be better, stretch further, and rest when I went too far. They inspired me to create How We’ll Win, Quartz’s now-annual special project on gender equality at work. Leading How We’ll Win, I interviewed 50 of the world’s most-powerful women in business, 50 of the world’s most-powerful men on masculinity and feminism, dug into today’s female founder landscape, and explored the next generation of female leaders.

I never would have seen this leadership opportunity if women in power at Quartz had not listened to my ideas and advocated on my behalf. These female editors paved my future, and our readership’s understanding of gender and power.

Writing How We’ll Win exposed me to many early-stage entrepreneurs and investors (especially Arlan Hamilton and Christie Pitts), from whom I learned the basics of VC and startup culture. Having spent years raising a brow at venture and #hustle, I was surprised to find myself spiraling into a deep obsession with sourcing and analyzing early-stage VC deals, markets, and emerging technology.

I couldn’t shake the idea that seed-stage investing required nearly identical skills to reporting (it’s the same diligence, EQ, network effect, and high-to-low level analysis). Mentors like Alexia Bonastos, a brilliant journalist-turned-VC and founder of her own fund, assured me that this hypothesis was correct — that being an amazing writer and reporter is an invaluable edge in VC.

So, inspired by the female VCs (and aware how few women there are in VC), I took the leap and quit Quartz to work in venture. I didn’t have a job, but I believed in myself, my ability to learn quickly, and the deep network of progressive VCs I’d cultivated over two years of cold emails and excessive Twitter use.

It wasn’t easy. For the first time in a long time, I was behind and pretty inept. I needed to learn how to love being criticized. Otherwise, and without any fanfare, I’d sink. VC is egregiously competitive, often cliquey, and notoriously opaque in its hiring practices. A lot of opportunities seemed awesome, then fell apart at the the eleventh hour. A lot of people lived up to douchey VC stereotypes. But many more people, I’d learn with time and patience, entirely defied my expectations. They were open-minded, excited by my abnormal background, and eager to mentor and learn with me.

Many of these VC mentors were women, and for their sponsorship and referrals I’ll be forever grateful (s/o Cat Lee, Alexia Bonatsos, Ann Miura-Ko, Tracy Chou, Monique Woodard, Anarghya Vardhana, Alex Marshall, Nashilu, Crissy Costa, Natalie Sportelli). Many were male feminists, like Nick Abouzeid and Yoni Rechtman. But my most impactful VC mentor was Will Quist, a partner at Slow Ventures. On paper, Will epitomizes almost every Silicon Valley stereotype. Besides his obsession with Patagonia and fly fishing, none of these stereotypes proved true.

While few other VCs saw benefit in hiring a journalist on the investment team, Will was actively searching for one. He was convinced that narrative expertise, concise writing (this blog post withstanding), fearless reporting, and interviewing skills were essential to intelligent investment decisions and long-term venture learnings. We immediately clicked, and I’ve spent the past six months working on contract for Will and Slow via an “experiment.”

Our work has been awesome. Will’s hypotheses were right. We’ve learned a ton, and annoyed one another just enough. My drive to stay involved in VC is stronger than ever. The founders I’ve met, worked with, or personally invested in (shout out Ethels Club, TTYL, Stix, Canopy, Projector, The Grand) have inspired me more than I ever expected. These founders are mission-driven, diversity-minded, and unwilling to compromise on quality or ethics. As my friends at Maveron would say, they’re unapologetically non-normal.

This passion for founders aside, I couldn’t see myself leaving my new path in VC for an operating role. I was privileged to be recruited to various startups, but nothing seemed right. As a journalist and investor my lens has always been breadth over depth. Focusing on one mission all day, everyday scared me. I’m unashamed to admit that.

Then I met Lindsay Kaplan and Chief. If there’s any critique I frequently face, it’s that I should probably tone it down and give more of a fuck about how I present myself. Unsurprisingly, I think that’s bullshit. When I met Lindsay, I immediately knew we’d be friends.

Not only is Lindsay a fearless, hilarious, and outspoken leader, she’s also a proven talent. Lindsay helped create and lead Casper’s brand. She was their first employee, and saw the company through its skyrocketing growth. She knows voice and brand better than anyone I’ve ever met. She has so much to teach me.

Equal in talent and character is Chief’s CEO and co-founder, Carolyn Childers. As Lindsay would say, “Carolyn is the brains of Chief, and I’m the soul.” Neither is more or less important, and the quality of humans Chief has hired and retained since last fall speaks volumes about the company’s management.

Chief’s mission and work embodies everything I believe in. If any thread ties this probably-too-long post together, it’s that I would not be where I am today without women in power putting themselves on the line to sponsor me. As important as it is to support young talent, such mentorship would never be possible if some women have not already risen.

Though I’ve never worked for an organization that’s founded or led by women, my success is indebted to the few women who — despite underrepresentation—fought for and earned their way to the top. The crazy thing is, once these women get there, they rarely find the support, community, or mentorship they need. Though the number of women in C-suite and VP level positions is gradually climbing, retention for women in these roles is stalling out.

When men reach the top, they’re bolstered by the old boys’ club they’ve long-known and loved. When women reach the top, they start to wish they never got there.

Chief is unwilling to wait for cultural change. Instead, they’re building the most-influential professional network in the world, designed exclusively by and for women who’ve reached the C-suite or VP level. From their clubhouse to their exclusive events, high-profile speakers, and landmark 10-person development cohort (which every member is placed in upon joining), Chief is creating the future of women and work.

www.chief.com

Since the 2016 election, I’ve repeated one quote (to myself and my friends) almost daily: “No force like women united.” I challenge you to find one woman who does not partially, or entirely, credit her professional success, happiness, and stability through the toughest times to her female friends, family, or colleagues. Women get the job done, and Chief is uniting them from the top down.

I am thrilled to be bringing editorial skills, brand enthusiasm, and hopefully an important voice to the Chief community. I cannot wait to learn from and grow with Carolyn, Lindsay, and the outstanding Chief team.

I’m also excited to leverage my new Chief network for continued work in the early VC ecosystem. I look forward to staying in close touch with the friends and mentors I’ve met in VC, and will continue sending you probably more deals than you’d like. I can guarantee that via Chief, there will be no shortage of top-tier female, and feminist founders.

My first day at Chief will be Monday, August 5. Please reach out and stay in touch: @LeahFessler on Twitter, and leah@chief.com

Thank you so much for your support.

Leah Fessler

Written by

Journalism, VC, early-stage startups. Thinking about gender, equality, and pugs. Formerly at Quartz, Bridgewater Associates, Middlebury. Words matter in tech.

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