Move beyond founder-led sales — and set up the next revenue leader to win.
When helps employers take care of departing employees, moving them off COBRA into better-fit coverage. The product was working and a Series A was underway. But go-to-market still ran through the founders, without a documented sales process, a clear ideal customer profile, or reporting leadership could rely on.
The founders knew they needed a full-time revenue leader. They also knew a strong one wouldn't sign up for a cleanup project. The goal was to build the structure first, so the right CRO could step in, take the baton, and keep it running.
Audit first, build the structure, then hand over the baton.
It started with a four-week GTM audit of When's strategy, sales, marketing, RevOps, technology, and brand. Jess then stepped in as interim revenue leader — running weekly sales and pipeline meetings, coaching the team, and presenting to the board — while building the structure underneath.
Process & RevOps
Documented the ideal customer profile and sales process, and rebuilt HubSpot around clean data, consistent deal stages, and pipeline reporting leadership could trust.
Pipeline engines
Launched account-based marketing on 200 named accounts, onboarded and activated several strategic partnerships, formalized the marketing strategy and performance reporting, and wrote When's first customer case studies.
The right leader
Recruited When's first CRO and a RevOps & Sales Enablement Lead, then co-piloted the transition so the motion kept running without the founders.
What changed for the business.
- Took the founders out of the middle of every deal with a documented ideal customer profile, sales process, and playbook the team could run.
- Gave leadership numbers they could trust: a rebuilt HubSpot with consistent deal stages and pipeline reporting ready for the board.
- Built a pipeline worth managing: $20M+ in new pipeline created across direct sales and partners.
- Opened a partner channel: onboarded and activated several strategic partnerships that started producing enterprise opportunities within weeks.
- Focused sales on the accounts most likely to buy with ABM on 200 named accounts and buying-signal alerts in Slack and HubSpot, powered by ABM Intel.
- Sped up buying decisions with social proof: wrote When's first customer case studies and took reviews from zero to 12.
- Gave marketing a plan and a scoreboard: a formalized marketing strategy and performance reporting tied to pipeline.
- Made When easier for buyers to find: organic search traffic up 176% over six months.
- Recruited the leader to run it: the structure in place helped attract Brook West as When's first-ever CRO, alongside a RevOps & Sales Enablement Lead.
- A clean handoff: Brook started June 1 with the foundation already running, and Jess co-piloted the transition.
