Growing average deal size substantially without slowing the sales cycle down — proof that expansion doesn't have to cost velocity.
Warmly was closing deals reliably, but at the smaller end of its market. The company had made the strategic call to move upmarket into Mid-Market and Enterprise accounts — but the existing outbound motion, discovery process, and positioning were still calibrated for smaller, simpler buying committees.
I self-sourced a pipeline of Mid-Market and Enterprise opportunities through a combination of LinkedIn outreach, cold calling, and personalized outbound, rather than waiting on inbound to catch up to the new target segment.
I owned the full sales cycle for these larger, more complex deals — prospecting and discovery through demo, negotiation, and hand-off to Customer Success — adapting the discovery and demo approach to match how larger buying committees actually evaluate and decide.
I ranked among the top Mid-Market/Enterprise AEs company-wide, and helped grow average deal size substantially while holding sales cycle length steady — evidence that the upmarket motion could scale without adding friction. Warmly went on to enter an agreement to be acquired by HubSpot in 2026.
This is the exact gap a lot of post-PMF companies hit: the product has outgrown the sales motion. The fix isn't just "sell to bigger companies" — it's rebuilding discovery, positioning, and pricing so the motion can actually support the deals the product is capable of winning.