Pasito Secures $21M in Series A for AI-Driven Group Health Workspace

There is a moment in every industry when the noise drops and the signal steps forward. Benefits has been overdue for that moment. Too many PDFs, too many handoffs, too many hours burned translating human needs into spreadsheet theater. Then Pasito shows up, not loud, not desperate, just precise. Built in New York, founded in May 2021, and engineered around the idea that work should actually work, Pasito just closed a $21M Series A and the timing feels less like luck and more like inevitability.

This round was led by Insight Partners, with participation from Y Combinator and MTech Capital, plus returning believers Core Innovation Capital, Segal Ventures, FiDi Ventures, and Susan Ehrlich. When Alexandra Lundin, VP at Insight Partners, Aaron Epstein, Group Partner at Y Combinator, and Brian McLoughlin, Partner at MTech Capital, line up behind a company, it is not because the deck was pretty. It is because the infrastructure underneath the industry is cracked and someone finally brought the tools instead of another memo.

Pauline Roteta, CFA, CFP®, did not come at this from theory. She came from BlackRock, from portfolio pressure, from watching a family member burn hours trying to make sense of benefits that were supposed to help, not confuse. That frustration became Pasito, alongside founders Julie Scotland and Ignacio Ampuero, building an AI-native workspace that turns unstructured chaos into a single operating environment across health, life, and retirement benefits. Sales, quoting, enrollment, support, claims, all talking to each other like adults.

The results read less like hype and more like math. 50x ARR growth in 12 months. Deployments across thousands of employers. 45% higher supplemental elections. 44% of non-contributing employees starting retirement contributions within 6 months. 2x HSA elections with 80% higher contributions. Families saving over $1.2K on medical expenses. Employers with 1,000 people cutting up to $1M in wasted spend. That is not a slogan. That is leverage.

Under the hood, Pasito’s agentic AI converts plan documents and census data into a unified data layer with 98% accuracy, while the industry averages 74%. It plugs into over 200 payroll systems like ADP, Workday, and UKG, speaks Spanish, texts employees when it matters, and keeps everything HIPAA compliant and SOC 2 certified. This is not AI for demos. This is AI clocking in every day.

Partnerships with Reliance Matrix, New York Life Group Benefit Solutions, and Sun Life U.S. are not logos, they are signals. Signals that carriers, brokers, advisors, and employers are done babysitting broken workflows. With this capital, Pasito is scaling engineering, expanding automation, and letting customers build their own agents inside the workspace. Less swivel chair. More clarity. Fewer benefits headaches. More people actually using what they are offered.