About

Colin Dowling

Founder, RAINCLOUD
  • SVP Revenue @ Alembic — Pre-Seed to $145M Series B
  • VP Global Enterprise Sales @ GoDaddy (NYSE: GDDY)
  • VP Channel Sales @ Liquid Web
  • 2x Founder
  • Texas-based, part-time Canadian.
  • Darth Vader. Barry Bonds. Red Bull Racing. Astros Baseball.
Colin Dowling, Founder of RAINCLOUD

When I was younger I played a lot of poker. At casinos, with friends, online. And I learned a universal truth most poker players understand: I can't remember the biggest pots I ever won, but I remember with excruciating detail every bad beat I ever suffered.

In the last 25 years of B2B selling, I've won some incredible deals — including GoDaddy's largest-ever enterprise contract, WP Engine's first five-figure monthly hosting contract, and Alembic's first true enterprise deal. And still, the details I remember most clearly are the deals I didn't win. The ones where I felt blindsided at the finish line. Where I had the verbal approval for an order form that never came. The ones where I later learned a deal I had committed to the board had gone to a competitor.

Sell for long enough and your own "bad beats" start to stack up. If you've made it this far, they probably already have.

I don't believe the best product wins. I believe the best salesperson does. And when I lost a deal I took it personally — the other person with a seat at the table outsold me.

The better salesperson won.

Each time I wondered: what could I have done differently? What should I have known? What could I have known? How could I better stack the deck in my favor for the next deal, and the next, and the next...

RAINCLOUD exists to give B2B sales leaders and their teams the exact intelligence they need to win more deals.

I built RAINCLOUD for me long ago and I've seen it work for me, my teams, and my clients.

If you think your team's close rates should be higher, if marking something "closed lost" stings, or if you're tired of being haunted by the deals you know you should have won — we should talk.

Not ready for that? Start with our ROI Calculator to understand the impact RAINCLOUD can have on your team and your business.

Colin Dowling, Principal @ RAINCLOUD — Founded 2018