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: STARTED FROM THE BOTTOM
Straight out of school, I was rejected by every tech company I applied to. I began working for 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.
BREAKING INTO TECH: FULL CYCLE AE
Next, I found myself at a startup in Cambridge, MA. Despite the office being in the back of a church, to me, this felt like making it to the NFL of Sales. I signed on with a $50k salary, a 40% raise from my last position. I quickly made it to the top of the leader board. The company was acquired, our VP took a new gig, and brought me along for the ride.
ACCIDENTALLY IN CHARGE: FIRST TIME LEADING
After an early shakeup, I was tapped by the CEO to run all of revenue. Sitting in the exec team meeting and presenting to the board for the first time. Great run from $0 to several million in ARR. On the way out, my CEO was well intentioned when he suggested I “wasn’t a startup guy” – that I had the ability to run big teams at Salesforce or Oracle. Hearing this stung deeply. I had other plans.
BUILDER MODE: JOINING A 10 PERSON STARTUP
I wanted to build, I didn’t want to maintain. The company was only doing $500k in ARR but I saw what it could be. With a chip on my shoulder, I wanted to prove that I could build a world-class revenue engine from scratch. I loved the product, the team, and the challenge. We had no choice to figure it out, so we did!
A CHAMPIONSHIP RUN: CRO OF THE YEAR
We built something incredible. As a revenue driven organization, our team scaled LinkSquares from $500K to $50M+ ARR with a 200-person revenue org. It was a peak ZIRP, covid-era cannonball run. Pavilion named me CRO of the Year (that guitar was the trophy)… but all good things come to an end.
FROM CRO TO CEO: STILL SOMETHING TO PROVE
From BDR to CRO in 8 years, every step of my career has been defined by steep learning curves. From my football days to the sales floor — I’ve always been obsessive about accomplishing the things I set out to do. Now comes the hardest role in tech: taking a company from $0 to $1M as a Founder CEO. No role requires more range. No challenge is bigger.
AI is a once-in-a-lifetime chance to build something truly special for the profession that gave me everything.
I’m building not just for Sellers everywhere— but to prove to myself, and to everyone watching, that we can do this.
