How To Close Enterprise Deals in Founder-Led Sales

​As startup founders trying to sell into the enterprise, we’ve all heard these remarks before: “Great demo” then crickets, or “this is awesome but we have some other priorities right now, can we regroup in a couple of months?” We’ve also seen pilots or proof-of-concepts (POCs) that don’t lead to closed deals, difficulty getting to the right people involved, or seemingly positive conversations that don’t move the deal forward.

​The good news:  many of your lost deals were your fault.

​Many of the causes of mid-funnel deals stalling or challenges with closing deals are preventable with some basic tactics for navigating complex buyer environments.  The session will provide some immediately actionable and practical tips for diagnosing problems, keeping deals moving, and maximizing value.

​Note: This session is designed for startup founders. Space is limited, and preference will be given to early-stage founders. Final location details will be shared upon approval.

​Sponsored by Davies Ward Phillips & Vineberg.

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​Toronto Tech Week is a citywide celebration of the people building what’s next. From May 25–29, 2026, founders, investors, and builders come together for hundreds of community-led events across Toronto, connecting tens of thousands of people around Canadian tech. Torontotechweek.com.