Jean Kim Smart had a workplace retirement plan from the start of her adult working life. Her parents had a grocery store, a dry cleaner and restaurants. They worked, employed people and raised a family. They had no retirement savings. The benefit that accompanied her career in finance had never become part of theirs. You could spend years studying the retirement industry and still miss the significance of that difference. Smart could find it by looking across her own family.
Her company, Penelope, grew out of that difference. She wanted small employers and their workers to have access to the kind of retirement arrangements she knew from larger organizations. The name belongs to her daughter. It puts a person at the end of a long financial calculation: someone who will inherit the consequences of decisions made years before she has to make her own.
That is a useful place to begin with Smart. Financial technology can sound as though its natural habitat is a presentation screen. Her story begins with people earning a living, trying to keep a business running, and hoping their children will have choices.
A child at the business end of the mail
Born in Korea and raised in Southern California, Smart grew up helping her parents interpret documents and do bookkeeping. A tax form arriving in a language you do not comfortably read makes a small business feel rather less small. The child who can explain the envelope becomes part of the machinery that keeps the place operating.
She grew up in Claremont. Her family’s move to the United States included a separation: her parents went ahead, leaving the three children with their grandparents in Korea before bringing them over. Smart was the eldest. Later, school made her conscious of being the only Asian child in her classroom. She learned to adjust between the American world of the school week and the Korean family world of the weekend.
Berkeley offered a different experience. At the University of California, Berkeley, where she earned a BA, she found a community of Asian students. The relief of belonging matters in her account. So does the effort of adapting before she found it. Long before she would lead a company, she had practice understanding the expectations of different rooms.
The benefit that came with the job
Her career began as an analyst at Goldman Sachs, followed by consulting at Deloitte. Charles Schwab, TD Ameritrade, Citigroup and UBS became further chapters. She worked in product, marketing and sales strategy, with a recurring focus on the services employers provide to workers. These included retirement plans and stock plans. The institutions changed; the connection between a job and a financial future kept returning.
At TD Ameritrade, her work included offer development and sales strategy from 2009 to 2015. Citi followed, with a global marketing role. From 2019 to 2021 she was a managing director and head of business strategy at UBS. Her professional world had budgets, established processes and the institutional knowledge required to make financial services work at scale.
A colleague who worked with Smart at both Schwab and TD Ameritrade has described her ability to consider the people and teams affected by a new initiative, from clients to technology and service staff. That is a particularly useful habit when a product has to travel through several hands before anyone benefits from it.
Offer development & sales strategy
Managing director
The founder chapter begins
A new route to the same customer
The question was what to do with that knowledge. Her parents’ experience gave her a reason to take it somewhere smaller. Institutional expertise is portable. Institutional economics, staffing and paperwork may need a little more persuasion.
A company named for the next generation
Smart founded Penelope in 2021. It launched publicly in January 2022, and that March announced a $2.1 million pre-seed round led by Slauson & Co. Amplify LA, Black Jays and executives from Wells Fargo, Citigroup and US Bank also participated. The announced uses were straightforward: build the self-service platform, expand the team and bring customers aboard.
The initial offering included pooled employer plans, traditional 401(k)s and solo 401(k)s. A subscription model and automated processes were intended to reduce the administrative burden. For Smart, the audience included the family businesses and individual entrepreneurs whose working lives had fewer corporate benefits attached.
There is a blunt sentence in her explanation of the company’s name: “I don’t want her to be my retirement plan.” Affection and financial obligation can become tangled across generations. Naming the business after her daughter gives its purpose an unusually direct expression. Smart wants the next generation to have something to build on.
“I don’t want her to be my retirement plan.”Jean Kim Smart, on her daughter Penelope
The paperwork is part of the product
Smart’s early descriptions of Penelope put considerable weight on simple language and an intuitive experience. She understood the customer as a busy business owner whose attention had many competing claims. A retirement plan could be worthwhile and still lose the day’s contest against payroll, orders and everything else waiting on the desk.
She also talked about financial education that connects with people’s lives. Questions about stocks and bonds, life stages and family goals mattered alongside the account itself. Making something available is only one part of making it usable. The person looking at the screen needs to understand why it belongs in their life.
The photograph of Smart with Ted Benna brings that continuity into view. A retirement product can acquire new software and a friendlier interface while remaining connected to a much older question: how does money earned today support a life that continues after the job?
The managing director who had to make the decisions
Founding changed the texture of Smart’s work. In an established organization, responsibility can move through departments. At an early company, the founder may be dealing with hiring, finance, legal questions and business development in the same day. She described the decision to start as both the best and the hardest she had made.
Women in her Chief peer group encouraged her to make the move. That support mattered at a point when she was leaving a substantial corporate role. Entrepreneurship was a new setting for experience she already possessed, with a great deal left to learn.
Her 2022 daily routine included reviewing development work from an EMEA-based team early in the morning. Later came a walk with her husband, Nick, and their poodle, Zoom, during which the couple coordinated family logistics. Even the dog walk had an agenda. Somewhere between international development and breakfast, the household still needed to work.
In a December 2022 conversation, Smart said that if she were doing something else, she might have a restaurant. She enjoyed cooking and had grown up around restaurants. She also spoke about recording her parents’ stories during visits, preserving memories of their earlier lives. Alongside building a business for the future, she was making time to keep hold of the past.
Learning to stand beside the roller coaster
In 2023, Smart talked with Jerry Colonna about the fluctuations of entrepreneurship. Their conversation addressed her sense of responsibility for the business and the additional significance of being an Asian woman in fintech. The work carried the demands of a company and the awareness that other people could see themselves in its founder.
Colonna encouraged her to return to the reason she was doing the work, and to consider the entrepreneurial roller coaster from the ground. The image has an appealing economy. A founder can recognize that events are moving up and down without treating every movement as a complete account of herself.
Smart’s reason has a family shape. It connects her parents’ working lives, her own institutional career and her daughter’s future. That connection does not simplify every business decision. It supplies a reason to keep making them.
The next move goes through the specialists
Penelope’s route has developed. Its current account of the business dates a focus on independent third-party administrators, recordkeepers and advisors to 2025. The company now describes itself as building the software infrastructure behind retirement services. The small businesses remain part of the purpose; the specialists who serve them become the immediate customers.
Smart has explained the practical attraction of licensing and embedding the platform through existing channels. Reaching small employers directly can be difficult and costly. Advisors and administrators already have relationships with them. Better tools for those specialists offer a way to extend the company’s reach.
In April 2025, Penelope announced the addition of Marcia Wagner, Kevin Crain and Lisa Kottler as senior advisors. The appointments brought expertise in retirement regulations, financial services and plan design. A month earlier, Smart had been among the women featured in Rokt’s Women’s History Month celebration on the Nasdaq Tower.
The billboard is a visible moment in a career. The software underneath a retirement service is usually less visible. Smart’s work now asks her to attend to both the people who already know how to serve a client and the infrastructure that could help them serve more.
Her story returns, finally, to the family business. A shop can support a household for years while leaving its owners with little set aside. A daughter can work inside the institutions that provide a different outcome. Smart built a company at the meeting point of those experiences. Its name keeps the next generation in the conversation.