She spent a decade building the apps that moved your money. Then she went after the part fintech kept skipping: someone to actually advise you.
Jessica Chen Riolfi runs Uprise, a fintech that does something almost quaint in an industry obsessed with frictionless taps: it gives small business owners a real financial advisor. A human one. Paired with software that handles the busywork, so the advice stays affordable instead of staying rich-people-only.
That choice - keep a person in the loop - is the whole personality of the company. Most of fintech spent the last fifteen years removing humans. Jessica spent that same stretch inside those companies, watching what got lost. Customers at Robinhood had powerful tools and nobody to tell them what to do with them. The gap kept staring back at her until she built around it.
Uprise started by handing young professionals Wall Street-level financial plans for free. It has since aimed at a harder, messier customer: the small business owner, whose personal and business money are tangled into one knot. "The small business world," Jessica says, "is one where personal and financial lives are intermingled." Untangling that knot is the product.
The company is small on purpose - around two dozen people, roughly $4.7M raised, a seed-stage outfit with San Francisco roots and a CEO who works the way she ran businesses before: customers first, ship fast, do whatever it takes.
"Financial advisory combines personal and business finances."- Jessica Chen Riolfi
Start at the beginning and the through-line is obvious only in hindsight. Jessica left Dartmouth for J.P. Morgan and the investment banking grind - the place where you learn money from the institutional side, in spreadsheets and term sheets. Then eBay and Amazon, where money meets scale and consumers. Then Harvard Business School, then the part that mattered most.
At TransferWise - now Wise - she ran Asia. Fifteen countries. The job was growing volume in markets that each had their own rules, currencies and reasons to distrust a startup with their savings. She has talked about the company's quiet radicalism: showing customers the real exchange rate and the real fees, up front, because "customers come first." Transparency as a growth strategy, not a press release.
At Earnin she was Head of Product, working on instant access to pay - fintech for people who could not wait two weeks for money they had already earned. At Robinhood she consulted on the long-term roadmap. Six companies that, between them, taught most of America how to move, invest and access money on a phone.
And the lesson she carried out the door was a kind of absence. All these tools, and still nobody to call.
Uprise has raised roughly $4.7M across its seed journey, with a $3.3M round landing in October 2024. The cap table reads like a who's-who of operators: founders and execs from Stripe, SoFi, Gusto, Robinhood and Cash App, alongside Contrary Capital, Hustle Fund, Blank Ventures and TruStage Ventures.
Show the real fees. Reveal the real rate. Minimize the cost. The growth follows from the honesty, not the other way around.
"Move fast in order to get the product out there for customers." Lean methodology, hustle culture, do whatever it takes.
Every small business owner gets a dedicated human advisor. AI handles the grunt work so the advice stays affordable.
When Uprise took on therapists as clients, the team did not flatten everyone into the same chat-bubble funnel. Therapists value the personal relationship, so Uprise leaned into video calls. It is a tiny thing. It is also the entire thesis: meet people in the format they already trust, then let the software do the rest.
Jessica calls the rollout strategy a "crawl-walk-run type of embedded approach." Don't demand a big-bang integration from a partner platform. Start small, prove it, scale with the customer. It is patient in a way that startups rarely are - and it is exactly how you'd expect someone who grew a money business across 15 cautious markets to think.
"The small business world is one where personal and financial lives are intermingled."
"Customers come first, lean methodology, and hustle culture. Do whatever it takes, and move fast to get the product out there."
"We take a crawl-walk-run type of embedded approach with our partners."
"Financial advisory combines personal and business finances."
"The small business world is one where personal and financial lives are intermingled."
J.P. Morgan, eBay, Amazon, Wise, Earnin, Robinhood - then her own company. Few founders arrive having shipped at this many fintech landmarks.
She ran a cross-border money business across 15 countries before deciding the bigger gap wasn't transactions. It was advice.
Uprise launched by giving young professionals Wall Street-level financial plans at no cost - proving demand before charging for it.
LinkedIn · Crunchbase · The Org · Financial Health Network · Products That Count · Tearsheet · Convera · Finovate · Together Digital. Facts drawn from public interviews and profiles; nothing here is inferred beyond the record.