Jaclyn Chen has a complaint about slides. For a founder raising money, this is rather like a chef developing reservations about plates. Eventually, someone expects a presentation. Chen’s response was to do the writing first: a 42-page investment memo, assembled before the fundraising deck. The document had to explain what Benepass did, why the business mattered, and how it would grow. Only then could the argument be condensed for the screen.
Her explanation is practical. Investors often write their own memos to persuade an investment committee. Giving them a considered account of the business makes that job easier. Writing also exposes the places where a narrative has outrun its evidence. A sentence has fewer places to hide than an attractive chart. Chen eventually made the deck. By then, she had already done the difficult part.
“I hate slides.”
Jaclyn Chen, on her preference for memos
The habit suits the company she co-founded. Benepass deals with the space between what a company offers its employees and what those employees can actually use. That space contains rules, spending accounts, payment systems, and plenty of opportunities for confusion. Chen has made a business out of taking those details seriously. Her subject can sound dry until you remember whose money is involved.
From Carmel to the other side of the table
Chen arrived in the United States at four with her Chinese immigrant parents. After Richmond, Virginia, the family moved to Indiana, where she grew up largely in Carmel. She remembers being organized and liking to take charge. She also edited school newspapers. Those interests offer a modest preview of the work ahead: organizing people, making sense of information, getting a message into a form someone else can follow.
Her formal route ran through the Wharton School and then finance. At Goldman Sachs and TPG Capital, she worked in businesses where analysis and financial judgment mattered. Stanford’s Graduate School of Business followed, from 2017 to 2019. The sequence looks tidy on a biography. Its usefulness lies in the change it made possible: the person who had studied businesses would start accepting responsibility for one.
The first version of Benepass emerged from experience inside large employers. A generous benefits package could still be awkward to navigate. Fischer, her eventual co-founder, has recalled sharing a house with Stanford MBA students while working on engineering projects. Chen’s experience at Teampay helped her see an opportunity to apply modern payments technology to benefits. The founding connection was personal; the problem was familiar to all three founders.
Chen, Mark Fischer, and Kabir Soorya founded Benepass in 2019. The company joined Y Combinator’s Winter 2020 batch. Its premise put different benefit programs behind a common card and app, with financial technology handling the complexity underneath. A person should be able to find and use an employer’s contribution without becoming an expert in the machinery that delivered it.
The perk has to travel
The company’s timing gave that proposition an immediate test. When work moved out of offices, familiar perks lost their familiar setting. An office lunch has a geographical limitation that a benefits brochure may neglect to mention. Employees elsewhere still needed support, but the company could no longer assume that everyone would use the same thing in the same place.
Chen’s explanation of Benepass starts with personalization. An employer can set the boundaries of a spending program while leaving individual employees room to decide what fits. A work setup, a learning opportunity, or another eligible purchase becomes an employee’s choice within those rules. The company’s responsibility includes making those rules work at the point of payment.
That distinction keeps the idea grounded. Choice requires administration. Someone must determine eligibility, recognize an allowed transaction, track the balance, and connect the result to the employer’s systems. Chen’s finance background belongs in this story because the seemingly simple experience rests on financial operations. The card is the part an employee holds. Behind it sits the work that makes the promise credible.
By December 2022, Chen was describing a wider change in the relationship between employers and employees. Companies could provide resources without prescribing the same menu for everybody. The logic is easy to follow across a distributed workforce: equal consideration does not require identical purchases. The administrative challenge is allowing that variation without asking an HR team to negotiate every choice by hand.
Useful introductions, fewer interruptions
A founder must also persuade people to buy. Chen has spoken candidly about how unfamiliar that was after a career in analysis. One early prospective customer compared her presentation to a school project. She accepted the criticism. It is an unusually serviceable founder anecdote: the presentation needed work, the customer said so, and the business still needed customers the following morning.
Her later discussions of fundraising treat persuasion as work that can be organized. On the Startup Success podcast in 2024, she explored the parallels between enterprise sales and raising venture capital, along with the preparation that makes due diligence easier. Both ask a stranger to commit to an outcome that has not happened yet. Both reward an account of the business that survives detailed questions.
Chen is equally specific about what she wants from investors afterward. In discussing MVP Ventures, she singled out introductions connected to sales and talent. Connections to senior people leaders could develop into relationships well before a large company became a customer. That requires patience. It also gives the vague word “network” a useful job description.
She appreciated help that did not produce unnecessary reporting obligations. A founder’s attention is already divided among customers, hiring, product decisions, and financing. Another meeting earns its place by accomplishing something. Her description of investor support has the same economy as the benefits idea: put the resource within reach, and reduce the work required to use it.
A company with room for different lives
Inside Benepass, flexibility has had tangible consequences. In 2022, Chen described colleagues moving closer to family or trying places they had wanted to live. A remote-first company could accommodate those decisions. She also described inviting feedback at the end of meetings and one-to-ones. The relevant management question was whether someone could do the role and contribute to company objectives.
There is discipline in that formulation. Listening to a request does not promise that every request will be approved. It does promise a conversation. Chen connected retention with opportunities to grow, managers who help employees understand their next steps, and training that makes those steps possible. The workplace she described required explicit expectations alongside room for different circumstances.
The company’s current account of itself extends that idea to the product: its employees use the same benefits platform they build for customers. That creates a direct relationship between a workplace promise and a working system. Any unnecessary friction has an audience inside the company as well as outside it. The small details are harder to dismiss when colleagues encounter them too.
Chen’s reading offers another clue to her approach. She has named Adam Grant’s Give and Take as a favorite book. In discussing her business, she has connected a giving mindset with listening to customers and understanding what would help them. The useful version of generosity requires attention. A benefit selected without that attention can remain perfectly well intended and perfectly unused.
In January 2026, Benepass announced a $40 million Series B led by Centana Growth Partners, with FoW Partners, Portage Ventures, and Threshold Ventures participating. The company reported more than 250 employer customers globally and more than 4.5 million card transactions. Its revenue had more than doubled since January 2025, according to its own figures. Those are dated measurements of a business moving into larger, more complex employers.
For Chen, that expansion keeps returning to the same practical ambition: benefits people understand, use, and value. The larger the employer, the more individual lives a single program must accommodate. Her work now includes the infrastructure and organization required to keep those choices functioning at scale. The writing, the payments, and the management decisions each carry part of that responsibility.
Her public updates suggest she still watches the small encounters between people and systems. She has considered how employees might ask an AI assistant about unused commuter funds rather than opening an app. That is a product question with a very human starting point: people want an answer before they want another interface. Elsewhere, she has described a less technical change of scene, moving from an industry gathering to a Backstreet Boys concert at the Sphere. Even a founder interested in administrative detail can find other uses for an evening.
There is a pleasing continuity between the school newspaper editor and the executive who prefers a memo. Both jobs ask someone to decide what matters, put it in order, and make it intelligible to another person. Chen has given that instinct a financial form. Somewhere beyond the funding announcements and board meetings, an employee tries to use a benefit. The transaction is small. It is also the point.