Zero to Hero: Live with Woody Klemetson, the operator behind Jive ($85M) and Divvy ($2.5B)

Most of the best advice in B2B sales never reaches the people who need it. It lives in private Slack channels, late-night DMs, and the back of someone’s notebook from a quarter that nearly fell apart. Founders and sales leaders share it with each other for years. None of it ever makes it to a stage.

That’s the gap Zero to Hero is here to close.

We’re running it together with two friends who build tools for revenue teams: Supered and AskElephant. One leader. One hour. No panel, no sponsor reads, no pitch. Just the playbook they actually used, including the bad hires, the near misses, and the moves that saved the quarter.

Episode 1 is with someone whose career runs through every era of modern SaaS sales: Woody Klemetson.

Meet Woody Klemetson

Woody started out running his own marketing consultancy and a bootstrapped tech support business in Provo, Utah. Then he moved into SaaS and spent the next 17 years building sales teams, watching them break, and rebuilding them better.

The short version of his CV:

• Solutionreach, where he joined as a sales rep and worked his way up to Senior Sales Manager.
• LogMeIn, where he ran inside sales as a Director.
• Jive Communications, where he grew the team from 6 to 60 people and revenue from $20M to $85M, which set up the acquisition.
• Divvy, where he built the sales motion as VP of Sales that led to a $2.5B acquisition by Bill.com.
• Bill.com post-acquisition, where he managed 300+ people and merged two sales orgs after one of the loudest fintech deals of that cycle.

In 2023 he left to found AskElephant, an AI workflow platform for revenue teams. He’s spent the last three years pouring everything he learned about how sales orgs break (and how to fix them) into the product.

The best advice in sales leadership lives in private Slack channels and DMs between old colleagues. It never makes it to the people who need it most. That’s exactly what we’re fixing.

From the Zero to Hero manifesto

What you’ll walk away with

This isn’t a webinar where someone walks you through their highlight reel. It’s an hour with the person who actually made the decisions, told in plain English.

We’ll cover the moves Woody made at each stage, the things he wishes he’d done sooner, and the patterns that show up in every team he’s helped scale. Specifically:

• What broke at $5M that worked at $1M, and what to put in place before you cross the next revenue line.
• How to spot who can’t scale with you, and a kinder, faster way to make the call.
• When to fire the strategy, not the rep, and how to tell the difference.
• What changed at Jive to take a 6-person team to 60 without breaking the team.
• The Divvy sales motion that made a fintech in a crowded category worth $2.5B, and what would be different if Woody were building it today.
• How Woody picks AI tools now, and why most teams are still using AI to do the wrong half of the job.

Every session ends with 10 to 15 minutes of live Q&A. Bring your hardest question.

Why we’re doing this

Three companies. One shared mission: take the busywork out of selling so revenue teams can focus on customers.

• Supered is the easiest way to get your sales team to follow the process, with in-app enablement and real-time guidance that actually sticks.
• Portant is the #1 HubSpot app for sales documents. We turn your HubSpot data into beautiful, ready-to-send quotes, proposals, and contracts in seconds. 920,000+ users, 5.1M+ documents automated, and counting.
• AskElephant is AI workflow automation for revenue teams. It removes manual CRM updates, scales coaching to every call, fixes messy handoffs, and surfaces churn risk before it costs you the renewal.

We all see the same problem: revenue teams losing time, energy, and deals to admin and bad process. Zero to Hero is how we share the part you can’t buy with software, the first-hand experience of people who’ve already built (and broken) what you’re building right now.

The details

Who this is for

Founders, sales leaders, RevOps people, sales reps who want to lead a team one day, and anyone running a sales team that has crossed (or is about to cross) the point where the old way stops working.

If you’ve ever wanted to sit a 17-year sales operator down and ask, “OK, what would you do here?”, this is that hour.