Twilio Foundry: Win-Loss Insights into Pre-Sales ABM that Accelerated Enterprise Deals

This case study was created from an episode of the Product Marketing Adventures Podcast. It has been adapted into Dusted's case study format to preserve and showcase the guest's real-world experience. Written to preserve the voice of the true author, Brandon Penn.

I joined Twilio in 2017 on the solution marketing team during the company’s push to move upmarket and crack enterprise after going public. Twilio is a suite of communication APIs for SMS, email, voice, and more that companies embed into their products. My focus was competitive intelligence and win-loss analysis: digging into CRM data, interviewing customers who chose us, and—more importantly—those who didn’t, to understand why we were winning and losing deals as we scaled enterprise go-to-market.

The data showed losses to competitors in various verticals, but the number-one reason we lost deals was the status quo—prospects simply deciding not to move forward. They couldn’t grasp the full ROI impact of Twilio or where to start building across the API suite and how to extract value from different use cases. Enterprise sales cycles regularly ran six months or longer, and sales needed better ways to handle both competitive and “do nothing” objections while showing a clear path from first use case to expansion.

We stayed customer-obsessed—wearing the customer’s shoes—and went beyond CRM fields by speaking directly with prospects and customers. From those themes I partnered with product marketing to build battle cards, objection-handling materials, and tighter positioning. That work evolved into Foundry, our special-ops pre-sales program. We ran three core motions tailored by company size, industry, and digital-transformation goals (crawl-walk-run):

• “Art of the possible” / dreaming sessions that white-boarded the customer journey in their own words.
• Illustrated storyboards (via an in-house illustrator) that showed the end-to-end experience, then technical blueprints mapping how Twilio APIs connected to their existing CRM, ERP, and other systems so developers (or our expert-services team) could start building immediately.
• ROI and economic analyses that quantified impact.

Sales could submit an internal ticket to pull Foundry into deals; we also surfaced the program on the enterprise landing page and armed reps with customer social proof after closed-won deals. Everything was hyper-personalized—often delivered as 60-page decks with ongoing check-ins.

We built the ROI calculators in Microsoft Excel (preferred for macros) and Google Sheets, using benchmark data aggregated from customer stories and case studies on cost savings, time savings, and efficiency gains by industry and company size. Calculators lived in our CMS so reps could copy and tailor them live; complex analyses came back to the core team. Storyboards and technical blueprints were created with an illustrator and then handed to expert services or the customer’s developers. Later the messaging ROI calculator was productized on Twilio.com as a self-serve lead-gen tool. Enablement and an internal ticketing process let the global sales and SE teams engage Foundry at the right moments.

Once we armed reps with the storyboards, technical blueprints, and ROI analyses, sales cycles accelerated and we saw clear deal expansion as prospects understood how to start tomorrow and adopt additional use cases over time. Enterprise velocity improved on cycles that previously stretched six months or longer. The ROI calculator that began as pure sales enablement became a lasting growth channel that continues to drive valuable leads. Foundry itself remained a core part of how the Twilio enterprise team sells (later rebranded as the executive engagement program), complete with customer social proof that reps routinely drop into decks.