The Twilio transformation · 2023–2025
Cold start. No enterprise infrastructure. Twelve months later, a team closing seven figure Fortune 100 deals.
I inherited Twilio’s North America new business team selling into the Fortune 1000: 30+ product led reps, no hunting motion, no qualification discipline, and no forecast the team could trust.
Of plan, with $40M+ in ARR contracted.
Pipeline generation against target.
Enterprise revenue mix in twelve months.
Opportunity forecast accuracy, from under 50% to just above 70%, measured at day 45 of the quarter.
Rebuilt in six months. The number followed in twelve.
The first 60 days were about learning what was really happening.
By month six, the bench was rebuilt, the teams were verticalized, sellers were on site in the field with customers and partners, and a deal control playbook with real operating rigor was installed, including implementation of the Challenger Sales methodology. The rest of the operating discipline held the standard: six hard gates, AE self certification and manager sign off, the weekly cross functional Deal Walk, a new compensation plan, and a coaching cadence that reinforced it.
The results compounded over the following months. The enterprise revenue mix shifted from 25% to over 70%. Seven figure deals closed with F100 icons. Despite significant change management, plan attainment reached 126%, and $40M+ in contracted ARR followed.
Read the full Twilio transformation
In 12 months: rebuilt the AE and Director bench, verticalized the teams, got sellers in the field in front of customers and partners, multithreaded out of procurement into the line of business, and moved the entire motion upmarket. Challenger Sales methodology installed as the operating standard. Six hard gate exits. No category moves without AE self certification and manager sign off. A deal control playbook built from real gaps observed in the field, adopted into the culture so every rep ran the same way. The Deal Walk: a weekly cross functional cadence that drove the conversations that actually moved deals. A new comp plan designed to pay for the motion we wanted. A coaching cadence that raised the bar, built momentum upmarket, and made clear to everyone what great looks like.
The same operating discipline drove Zipwhip’s upmarket move: platform and systems hardening, cross functional coalition building, and an alliance strategy that won a highly competitive, regulated vertical against larger, better resourced competitors. I have also built enterprise revenue from zero at Glympse and operated at scale at AT&T Mobility.
Every stage. Every motion. The playbook adapts to where you actually are, not where you wish you were.