June 15, 2026  4:00 PM – 5:00 PM GMT+0
Mentor Office Hours

The Founder's Playbook for complex sales

Some deals change everything.

Not every win moves the needle the same way. A flagship customer, a strategic partnership, a joint venture, an acquisition — these are the deals that don't just bring in revenue. They change what's possible for your company.

But they're also the hardest to close.

Complex deals mean multiple stakeholders, long timelines, internal politics, and buying processes that have nothing to do with how good your product is. Instinct will only take you so far. At this level, founders need structure.

That's exactly what this session is about.

On June 15, Jonathan Lowenhar, Founder and General Partner at Enjoy The Work, is running a free, practical session for the Startupfest community on how to navigate complex, high-stakes sales.

You'll walk away knowing how to:

  • Identify the different types of players you’ll encounter
  • Map your customer’s buying process 
  • Move big opportunities forward without losing momentum

This is a preview of the operating frameworks taught inside the From Founder to CEO Bootcamp, coming to Montreal this July 6-7.

Presented by Enjoy The Work and Startupfest.

Founder & CEO
Enjoy the Work