Behind the Ascend Team
Build the systemsinsurance runs on.
Insurance moves trillions of dollars through fragile, outdated workflows. We’re rebuilding the financial infrastructure beneath it—carefully, correctly, and at scale.
Our MIssion
Insurance doesn’t fail loudly. It fails quietly—on spreadsheets, PDFs, and reconciliations.
The industry moves trillions of dollars, yet its most critical systems are fragmented, manual, and brittle. Small accounting errors don’t stay small—they cascade.
Ascend was built in response to that reality. Not to make insurance “feel modern,” but to rebuild the financial and accounting infrastructure it actually runs on. This work rewards people who think in systems, respect complexity, and are willing to be precise when speed would be easier. That’s the bar here.
Meet (some) Ascenders
The people who chose to take on the problem of insurance accounting — and stayed with it.
Andrew Wynn
Co-Founder, President
Andrew brings deep experience in building successful ventures, having seen firsthand how operation systems break at scale. Before Ascend, he co-founded Sheltr which he sold to Hippo Insurance, where the limits of existing infrastructure became impossible to ignore.
Praveen Chekuri
Co-Founder, CEO
Andrew brings deep experience in building successful ventures, having seen firsthand how operation systems break at scale. Before Ascend, he co-founded Sheltr which he sold to Hippo Insurance, where the limits of existing infrastructure became impossible to ignore.
Jot Ranu
Vice President, Strategy
Jot brings deep experience in building successful ventures, having seen firsthand how operation systems break at scale. Before Ascend, he co-founded Sheltr which he sold to Hippo Insurance, where the limits of existing infrastructure became impossible to ignore.
Ka Ki Fung
Engineering Manager
Ka Ki brings deep experience in building successful ventures, having seen firsthand how operation systems break at scale. Before Ascend, he co-founded Sheltr which he sold to Hippo Insurance, where the limits of existing infrastructure became impossible to ignore.
Eddie Ruvalcaba
Engineering Lead
Eddie brings deep experience in building successful ventures, having seen firsthand how operation systems break at scale. Before Ascend, he co-founded Sheltr which he sold to Hippo Insurance, where the limits of existing infrastructure became impossible to ignore.
Shyam Sivakumar
Head of Data
Shyam brings deep experience in building successful ventures, having seen firsthand how operation systems break at scale. Before Ascend, he co-founded Sheltr which he sold to Hippo Insurance, where the limits of existing infrastructure became impossible to ignore.
Together, we build Ascend with a shared belief that infrastructure work done carefully, compounds. And shortcuts eventually surface.
Our expertise isn't homegrown. It's picked from the halls of industry leaders with a track record of shipping quality products.
Life at Ascend
We take the work seriously, and we’re intentional about how people are supported while doing it.
Building infrastructure that moves real money requires focus, patience, and trust. We design our environment to support deep work, clear communication, and long-term growth — not performative hustle.
Values
How we approach work
Speed with direction is our greatest superpower; the simpler things are, the faster we can move; the faster we move, the faster we succeed.
Benefits
How we support you
• Competitive salary and equity with 401k employer match• 100% medical, dental and vision coverage for you and your dependents• 14 weeks parental leave for primary caregivers, 8 weeks for secondary
Open roles
Join us in building the financial infrastructure insurance runs on.
Don't see the right role?
Reach out
here.