Build the systems insurance runs on.

Our San Francisco office

The Ascend team at our SF office

Focused. Supported. Well-rested.

Gabby & Amelia from ISU Steadfast 2026

Insurance moves trillions of dollars through fragile, outdated workflows. We’re rebuilding the financial infrastructure beneath it — carefully, thoughtfully, and at scale.

Our Mission

Insurance doesn’t fail loudly. It fails quietly, on spreadsheets, PDFs, and in reconciliations.

The industry moves trillions of dollars, yet its most critical systems are fragmented, manual, and brittle. Small accounting errors don’t just stay small, but 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.

Meet (some) Ascenders

The people who chose to take on the problem of insurance accounting — and stayed with it.

Praveen Chekuri

Co-Founder, CEO
Praveen brings deep technical and product engineering expertise building complex systems and leading cross-functional teams. Prior to Ascend, he co-founded an insurtech with Andrew that was acquired by Hippo Insurance. Before that, he held engineering roles at high-growth technology companies including Houseparty (acquired by Epic Games) and Instacart.

Andrew Wynn

Co-Founder, President
Andrew has over a decade of experience building technology companies that solve complex operational problems. Prior to founding two separate companies with Praveen, he worked in product management and operations roles at Looker Data Sciences (acquired by Google) and Instacart.

Jot Ranu

VP of Revenue
Jot oversees the go-to-market function at Ascend as VP of Revenue. She started her career at Parthenon (subsidiary of Ernst & Young), consulting and evaluating software companies, and then shifted into the startup world at The Athletic (acquired by New York Times), working on pricing and business analytics.

Ka Ki Fung

Engineering Manager
Ka Ki has first-hand experience scaling consumer lending products, including leading a zero-to-one credit expansion across Southeast Asia. Prior to Ascend, she held engineering leadership roles at Empower (now Tilt), where she also led product integrations for new acquisitions.

Eddie Ruvalcaba

Staff Software Engineer
Eddie combines experience with expertise with senior engineering roles at companies such as Hippo Insurance and Linkedin. He leads engineering at Ascend and has spent his career building high-impact web and mobile applications and leading cross-functional teams.

Kailyn Despotakis

Director of Agency Sales
Kailyn brings over five years of diverse sales experience across insurance, fintech, and HR sectors. At Ascend, she has partnered with agencies of all sizes from local scratch agencies to top 20 brokers and now oversees all strategic relationships as Director of Agency Sales.

Zoe Reinecke

Lead Solutions Consultant
Zoe brings experience in software implementation and platform adoption to her work at Ascend, where she helps insurance agencies automate their accounting workflows. Prior to Ascend, she led platform rollouts and adoption initiatives nationally and supported large-scale digital training programs across the US.

We build Ascend with a shared belief that infrastructure work, done carefully, compounds.

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

Choose velocity

01
Speed with direction is our greatest superpower. The simpler things are, the faster we can move; the faster we move, the faster we succeed.

Know your customer

02
Knowing and understanding our customers as both people and professionals is critical to Ascend’s success.

Own it

03
We are all owners. The greatest chance of success comes from thinking with that as our primary title.

Inspire with humility

04
Change is driven from the inside out. We have to humbly show & inspire, not tell, when there is a better way.

Give collaborative feedback

05
We win if we constantly push each other to grow and improve in a kind and compassionate way.

Benefits

How we support you

Stability

01
• 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

Perks

02
• $150/month company commuter benefits
• Covered in-office lunches
• Flexible time off (that we expect you to use!)
• Dog-friendly office

Open roles

Join us in building the financial infrastructure insurance runs on.

• Lead Customer Success Manager\ \ San Francisco, California\ \ Customer Success
• Product Marketing Manager\ \ San Francisco, California\ \ Marketing
• Product Operations Lead\ \ San Francisco, California\ \ Product
• Sales Development Representative\ \ San Francisco, CA\ \ Sales
• Senior Software Engineer\ \ San Francisco\ \ Tech
• Software Engineer\ \ San Francisco\ \ Tech
• Solutions Engineer\ \ San Francisco\ \ Tech

Don't see the right role?

Reach out to
talent@useascend.com.