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Founder at Dusted
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):
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