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FinTech Female Fridays: Meet Founder & CEO at Penelope, Jean Kim Smart

“Freedom is a feeling. The feeling is no fear. I mean no fear!”

- Nina Simone, Singer, Writer, Activist


This quote shared by Jean Kim Smart has been inspiring her to the power of no fear. In advance of Asian American and Pacific Islander Heritage month, we at NYCFintechWomen are proud to pass the power along.


Jean Kim Smart is the CEO of Penelope, a 401(k) plan for micro-businesses and solopreneurs, which came out of stealth mode in early 2022. The idea for Penelope started right before the pandemic with the goal of helping and reaching the people who have the least amount of resources yet the biggest hurdles - the mom and pops, the true bootstrap companies. The community response has been overwhelmingly positive between a lot of demand (and state mandates) driving smaller companies to have a qualified retirement plan. The Penelope team has a goal to reach 100k companies and over a million American workers who make less than $100k and wants to help them start building the foundation for generational wealth creation.



As a newly minted startup, Jean juggles business development and is the face of the company while also head of HR, finance, legal and more. "Have huge admiration for founders - we’re on the hook for everything so there’s really no hand off at early stage. It’s hard, then hard and then harder… but would NOT change anything for the world!" Jean says.


Jean started her career at Goldman Sachs as an Analyst, then moved to consulting at Deloitte and spent the next 20 years doing corporate strategy, marketing and product at Schwab, Citigroup and UBS. "My career on Wall Street followed the expectations of Asian immigrant parents (loving but tough). It took COVID to happen for me to say, I want to start my own company." Knowing how difficult it can be to navigate personal finance and build for a strong retirement, Jean took what she knew best to build a solution (Penelope) making it easy and straight-forward for micro businesses and solopreneurs to secure their retirement for themselves, their family and their employees. Jean is proud that Penelope is more than a “retirement” or “regtech company” company but a fintech that is a “generational wealth builder company” - Penelope is creating a more inclusive world by helping create generational wealth.


Jean and Ted Benna, who's considered the father of the 401(k)

At Penelope, about 90% of the employees and partners (lawyers, creative agencies and advisors) are women, people of color and immigrants. They are a group of people who get it and have lived it. Jean describes the team as ambitious, communicative, low-ego, helpful and “get shit done” type of people. "No matter how much we grow, we want to keep our culture as humble, direct and fast as possible. We are the change agents that understand these minority small businesses! Our team culture is tight and continues to grow and evolve." She adds: "I want more and more of us to always have a point of view, use logic, good judgment and experience to execute and then pivot and change when needed. Confidence and trust is critical."


Looking back, Jean describes founding Penelope as the best and scariest thing she has ever done - "The best decision I have made has also been the hardest." But she appreciates that her core team at Chief, a women’s network group, really encouraged her to go for it, to start a company, especially at a stage where Jean had a fairly big role. And she has not looked back. "One year in, it’s the best thing. I didn’t think I ever really fit in corporate America. I also didn’t think I could do this." But now, Jean is able to create long-term impact for many people and knows why these decisions need to be made. Jean thus wishes to inspire more women to the power of no fear: "My hope is that more women, regardless of their stage in their profession, break out on their own."


More on Jean


Where you currently live: West Village, Manhattan

Living arrangement: Got lucky with a spacious apartment during COVID.

Family at home: Lives with husband (Nick), daughter (Penelope) and poodle (Zoom).

Hometown: Claremont, CA

Favorite hobby: Cooking, going to museums, and kinda sad but working.

Favorite part of your day: working with my team (all whom have met IRL a few times) kill it and figure things out moment by moment.

Favorite show to binge: Morning Show, Search Party, Emily in Paris, Billions :)


Do you have any productivity hacks? What keeps you motivated? How do you maintain a work/life balance?

First is to align my work with family obligations. My husband and I do a daily early morning walk with our dog and figure out who is going to do what (not romantic but super helpful in making sure the household runs smoothly). As for work, we are so small and take on so much - we use Slack and regular cadence throughout the day to inform each other. Probably could work on this better.


What is the most important lesson you have learned from a mistake you’ve made in the past?

Trust my instincts and guts - they are not magical, yet informed by decades of experience. Believe and make decisions faster based on my instincts.


Daily Diary


4:00 am - 5:00 am - wake up and review dev team work based in EMEA

6:30 am - walk Zoom (our dog) with my husband and logistics plan for the day

7:30 am - breakfast with family

9:00 am - 6:00 pm - work, work, work

6:00 pm - 8:00 pm - prospect/business social event or dinner with family and friends

8:00 pm - 9:00 pm - Modern Family on in background while I work

9:00 pm - 10:00 pm - talk with family and friends on the West Coast



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