Meet the team
Most GTM AI is built by people who’ve never carried a quota—too complex and dependent on a GTM engineer. We’re building tools sellers love to use
Steve Travaglini is the founder and CEO of Winrate. Named Pavilion’s CRO of the Year in 2023, Steve went from BDR to CRO in just eight years, earning a reputation for building elite sales teams and scaling with precision.
Most recently, Steve served as Chief Revenue Officer at LinkSquares, an AI first player in Legal Tech SaaS. He designed and led the GTM strategy that propelled the business from $500K to $50M in under five years.
Steve’s mission is to lead the sales profession into the AI era with technology that is grounded in the very human way sellers think, work, and win.
board + advisors
Kyle York is a Board Director at Winrate and the Co-Founder and CEO of York IE, the firm that led Winrate’s pre-seed round. A lifelong builder and operator, Kyle has spent his career scaling B2B technology companies.
Kyle York is a Board Director at Winrate and the Co-Founder and CEO of York IE, the firm that led Winrate’s pre-seed round. A lifelong builder and operator, Kyle has spent his career scaling B2B technology companies.
Prior to founding York IE, Kyle served as Chief Revenue Officer at Dyn, where he helped grow revenue from $3 million to over $100 million before its acquisition by Oracle. At Oracle, he led product strategy for Oracle Cloud Infrastructure and helped shape the company’s approach to developer-centric cloud services.
Kyle brings deep experience as both an investor and operator, and plays an active role in guiding Winrate’s long-term vision, product strategy, and market expansion.
David Cancel is one of the most respected product founders in SaaS. He built and scaled Drift into a category-defining platform, leading it through a $1B+ acquisition by Vista Equity Partners.
David Cancel is one of the most respected product founders in SaaS. He built and scaled Drift into a category-defining platform, leading it through a $1B+ acquisition by Vista Equity Partners.
Before Drift, he rebuilt HubSpot’s product from the ground up as Chief Product Officer, helping shape the company’s trajectory through IPO.
As an independent board member at Winrate, David brings world-class product insight, operational rigor, and founder-level empathy. His influence helps shape not just what we build — but how we think, lead, and grow.
Manny Medina
Advisor, WinrateFounder & CEO, Paid.ai
Founder & former CEO, Outreach Connect on linkedin
Manny Medina is the Founder and CEO of Paid, the business engine transforming how AI agents are monetized. Previously, he co-founded and led Outreach from startup to $4.4 billion valuation, growing it to 6,000 customers, 800 employees, and $250 million in annual recurring revenue. At Paid, Manny is pioneering the financial infrastructure for the AI agent economy after recognizing that traditional SaaS pricing models (charging per seat or per user) simply don’t work when one employee can run dozens of agents or agents operate autonomously. Having secured €10 million in pre-seed funding led by EQT Ventures with participation from Sequoia Capital, he’s building the platform that ensures AI agents get paid profitably.
Manny Medina is the Founder and CEO of Paid, the business engine transforming how AI agents are monetized. Previously, he co-founded and led Outreach from startup to $4.4 billion valuation, growing it to 6,000 customers, 800 employees, and $250 million in annual recurring revenue. At Paid, Manny is pioneering the financial infrastructure for the AI agent economy after recognizing that traditional SaaS pricing models (charging per seat or per user) simply don’t work when one employee can run dozens of agents or agents operate autonomously. Having secured €10 million in pre-seed funding led by EQT Ventures with participation from Sequoia Capital, he’s building the platform that ensures AI agents get paid profitably.
A BDR to CRO Turned Founder
The BDR Days: Cold Calling & Climbing
Straight out of school, dialing for dollars at a family-owned staffing firm. Thousands of cold calls, tons of rejections, and moments of doubt. Something clicked—I was named rookie of the year and opened their first new office in a decade.
The Big Break: Getting My Shot
Next, I found myself as a Full-Cycle AE at Backupify – I finally broke into tech sales, making a splash with my big-league, $50k salary. Then the company was acquired, my mentor split, and brought me along for the ride.
The Leadership Call: Stepping Up
Sitting in the exec team meetings and presenting to the board for the first time. Great run from $0 to several million in ARR. On the way out, my CEO suggested I “wasn’t a startup guy”—that I’d be perfect running large teams at Salesforce or Oracle. I had other plans.
Taking a Risk: Betting on Myself
I took a big risk joining a 10-person startup doing only $500K in ARR. With a bit of a chip on my shoulder, I wanted to prove that I could build a world-class revenue engine from scratch. The team was gritty, budgets were tight, but we had to figure it out. So we did!
The Championship Run: CRO of the Year
Scaled LinkSquares from $500K to $50M+ ARR with a 200-person revenue org. Pavilion named me CRO of the Year. We’d built something extraordinary… but all good things must come to an end.
From CRO to CEO: Breaking Free
Sales was the vehicle I used to change my life. Now I’m building Winrate to help sellers do the same. AI is a once-in-a-lifetime opportunity to empower salespeople, not replace them. We’re keeping humans at the center where they belong.
