Q&A With Cercle AI’s COO Ashley Finch on How to “Lean In”

Ashley Finch is the COO of a women’s healthcare AI start-up, Cercle AI. Before taking this leap, she held leadership roles at Meta and Lean In, where she worked closely with her former mentor and boss, Sheryl Sandberg.

Her journey is one of bold choices. She turned down an executive role at Google—one of the most powerful tech companies in the world—to take on the uncertainty of a startup that she describes as dream role, driven by a deeply personal mission and her own health challenges.

“I also spent years working for Sheryl Sandberg telling women all around the world to Lean In and do the thing(s) you would do if you weren’t afraid. The Google vs. Cercle decision was my “why not now” Lean In moment,” says Ashley Finch. 

Find out more about her bravest moments, her biggest challenges, and invaluable advice for female leaders. 

What inspired you to join Cercle as their COO?

Throughout my career, I’ve worked for companies that leveraged data and insights to drive positive change. From my agency and consulting days at Burson-Marseller and McKinsey & Company to my time at Lean In and Meta, leveraging data to drive positive change (in both companies and the world at large) has been a driving force behind each organization.

Along comes Cercle AI and my introduction to Juan Carlos Riveiro, Cercle’s CEO and founder, who was on a search for the company’s first COO. Cercle is all about transforming healthcare data at scale into insights that will improve the entire women’s healthcare ecosystem and provide more personalized care to women. Women spend 25% more time in “poor health” than men and research to improve women’s health is massively underfunded.

I was completely energized by Cercle’s goal to produce richer data for women’s healthcare companies – and I strongly believe the work we are doing to unlock insights will improve access to women’s healthcare, drive research into conditions that disproportionately impact women – and ultimately lead to better health outcomes for women.

Beyond the mission, I joined our CEO & founding team at Cercle because it checked all of the critical boxes on people, product, and scope. The start-up was run by a world-class and experienced bench of successful founders – and was also backed by a former mentor and boss, Sheryl Sandberg, and other incredible investors. The Cercle products and their impact on the women’s health industry deeply resonated with me and my own fertility journey. And I was hungry to gain the experience of operating a 0 to 1 business from the ground up.

All of that together made this a dream “next” role.

What is the bravest thing you’ve done while on your journey? 

Personally, the bravest thing I’ve ever done is to go through 12 IVF cycles over the course of 3 years to have my two kids. I was fortunate enough to be at a company at the time (Meta) that helped cover many of the costs and that is unfortunately a luxury not afforded to almost all women experiencing infertility.

My infertility — and all the resulting ups and downs that came with it — is equally my greatest gift and greatest challenge in life.

After leaving my role at Meta, I had the decision of joining Google for an incredible executive role on their Strategy & Operations team or joining Cercle as COO. Obviously both were incredible opportunities but I went for the role that came with higher risk, less financial security, and 100x the ambiguity and uncertainty.

One of my fellow Board members and a close colleague at Cercle is Amy Jo Martin. Amy is a NYT best-selling author and has built a media brand and movement around the simple question of “Why Not Now?” She believes the world will be a better place if more people ask themselves what they would do now (removing all constraints) — and then take the actions to go do it. I also spent years working for Sheryl Sandberg telling women all around the world to Lean In and do the thing(s) you would do if you weren’t afraid. The Google vs. Cercle decision was my “why not now” Lean In moment. Why not go be a COO of an AI start up now (even though it’s something you’ve never done…in a new industry…with completely unknown outcomes)!

What is a non-negotiable in your routine that keeps you focused?

1. Quality time with my family

2. Sleep – I rarely get fewer than 7 hours, and usually more!

Working out has always been more of a chore for me than a non-negotiable — and I envy people who just love it. But staying healthy and strong is obviously so important (and helpful for focus and stress, too!) so I have found ways to integrate cardio and strength-building workouts into my routine.

The context shifting from COO to “mom” mode is challenging, and it’s a part of my daily routine I am still figuring out. Like so many working moms, I go from daytime work intensity “GO” mode to evening “let’s play trains and dolls” and parent/toddler negotiation mode. I need to be better at going off of Slack and my laptop in the evenings but boundary-setting in early stage start-ups (particularly with a remote, international team) is a work in progress for me.

What has been your biggest challenge while on this journey? 

The biggest challenge for me as a start-up COO has been staying clear-headed and steady despite the massive ups and downs of seed stage companies. Building companies from 0 to 1 is really, really hard. Some days feel existential (who are we, what are we building, where are we going) and other days feel completely exhilarating (a huge customer is delighted, we close a big deal, we learn and grow as a team).

Mental mantras have been really powerful for me. Saying things like: “doing this matters for women everywhere” “I am learning and growing so much” “Nothing is permanent”. Mantras like this help build my own resilience so that I can weather the storms of start-up COO life more effectively.

I’m also in the process of building out a team that is so incredible to work with and that I learn from every day. If you are surrounded (even virtually) by people who you care about, it makes all the challenges feel lighter and easier to navigate.

And having a true partner at home has also been critical in navigating the ups and downs.

What advice would you give to other female leaders and entrepreneurs?  

I love lists so here are my top 5.

1. Don’t borrow trouble from the future. I say this to myself, my family and my team several times every week. Focus on what you can control now. I love the quote “if it’s out of your hands, it deserves freedom from your mind too.”

2. Similar to 1, I wear a necklace every day that says “un pied devant l’autre”, or “one foot in front of the other” in french. It’s my constant reminder to focus on the next thing in front of me and take it one day at a time, one step at a time, one decision at a time…

3. I think of myself as a generalist and an operator, but for years I was navigating the trade off of being a generalist vs. a specialist. There are pros and cons to being a generalist — and I always encourage leaders to make this choice deliberately and earlier on around the mid-level manager level. The book Range by David Epstein is an excellent read for people debating the “generalist” vs. “domain expert” trade offs.

4. I always encourage leaders to flex throughout their careers between different types of roles and/or organizations. I’ve worked at early stage start-ups with fewer than 10 people and large, global public companies with 100,000. My toolkit as an operator can now take the best from both worlds.

5. Most female leaders know this but it’s always a good reminder to look at the data on women’s leadership. The numbers aren’t moving. We are earning the majority of college degrees (~60%) but still, only make up 11% of Fortune 500 CEOs. And if you look at promotion rates across companies, women are 20% less likely than men to get promoted AT THE FIRST promotion (from entry level to manager). As leaders, we need to make sure we’re aware of these macro trends and how they might take shape in our own organizations. Is the playing field level when it comes to pay, promotions, and hiring within our own companies? Data is power and we all need to be looking at the data and having these conversations in our own organizations.

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