In this episode of Culture Uncovered, Jena Dunay sits down with Matthew Brunwasser, Head of People Ops at Coverdash, to explore what it's like to build culture at a fast-growing, tech-forward commercial insurance company serving small businesses and contractors.

Matthew shares his unconventional path into people ops — from 13+ years running restaurants and poke bars in New York City, to agency recruiting post-COVID, to head-of-people roles at Bbot (acquired by DoorDash) and Sauce — and how a direct LinkedIn message from Coverdash's CEO led him to an industry he wasn't initially passionate about, but a team he immediately connected with. The conversation dives into how Coverdash maintains an ”evolving collaboration” culture across a truly distributed workforce spanning the US, Serbia, and soon Latin America, including a core overlap window for real-time communication and heavy use of Loom videos to bridge time zones asynchronously.

The episode also covers Coverdash's benefits philosophy — built directly from employee engagement survey requests rather than guesswork — its responsible PTO policy that rewards results over face time, and an honest reflection on the challenge of building genuine personal connection across a workforce that tripled in just over a year.

What You'll Learn

• How Coverdash uses technology to modernize commercial insurance for small businesses and contractors
• How a distributed team across the US, Serbia, and soon Latin America stays collaborative despite major time zone gaps
• Why Coverdash relies heavily on Loom videos instead of long Slack threads or waiting for same-time availability
• How the company's ”responsible PTO” policy ties flexibility to performance rather than time logged
• Why Coverdash builds new benefits directly from engagement survey requests instead of guessing what employees want
• An honest look at the challenge of fostering real personal connection across a workforce that tripled in just over a year

Company Highlights

• Industry: Tech-driven commercial insurance (insurtech) for small businesses, contractors, and consultants
• Customer Base: Small businesses and independent contractors historically underserved by traditional insurance carriers
• Company Stage: 4-year-old, Series A-funded company; ~95 employees (doubled in under a year), nearing profitability
• Culture: Evolving, collaborative, and intentionally built around flexibility and trust over rigid structure
• Focus Areas: Sales and operations growth, internal tech upskilling, leadership development, and cross-timezone connection

Unique Perks & Programs

• Responsible/Flexible PTO: Performance-based time off with no cap, exemplified by a top performer who took six weeks off in a year
• Survey-Driven Benefits Rollout: New benefits (like a recently added 401(k) and match) launched directly in response to employee survey requests
• Manager Book Club: A quarterly leadership development program (recent reads include Radical Candor and Who) paired with accountability check-ins
• Internal Tech Demo Days: Regular sessions teaching non-technical employees to build and use internal tools without relying on engineering
• Strong Internal Promotion Track: Nearly all current leaders, including the lead software engineer and sales/ops team leads, were promoted from within
• Expensed Team Bonding Trips: Spontaneous, leader-initiated outings (like a golf trip for the Rochester team) without requiring prior budget approval

To learn more about Coverdash:

Careers Page (they're hiring!)
LinkedIn Page
Matthew's LinkedIn
Small Businesses looking to confirm they have the best rates and policies possible