Client Case Study
Gareth Ouellette
Director of Product Management at Twilio
Before & After
Gareth was overconfident, relying on his deep experience and aptitude to carry him through interviews, and struggled to acknowledge that something fundamental needed to change even as he repeatedly fell short at the final stage.
Gareth opened himself up to honest self-assessment, became comfortable with being uncomfortable, and fully committed to the coaching process — recognizing that excellence, not just aptitude, was required to land the role.
Gareth initially relied on a single internal contact to refer him into the process at Twilio, which he recognized was not sufficient on its own.
Gareth proactively expanded his network inside and around the company — reaching out to multiple current and former employees — to gain a wide range of perspectives and build broader internal support before and during the process.
Gareth had a broad set of stories mapped to competencies but they were not tailored enough; he was getting caught off guard by certain interview formats and could not close at the final round, finishing as a runner-up in multiple processes.
Gareth practiced intensively with coaches multiple times per week, perfected one precise, highly tailored story per key topic, and was able to deliver narratives that directly answered what interviewers needed to hear — ultimately landing the offer at Twilio.
Gareth was participating in many long interview processes (6–8–10 weeks each) but converting none to offers, spreading his effort without the focus or deep preparation needed to close at the final stage.
Gareth became highly selective, deeply researched his target company's business dynamics, competitive landscape, and go-to-market, and prepared a full product strategy before even meeting the hiring manager — turning his effort toward quality over quantity.
Gareth was earning a certain level of compensation at his previous company but had not yet secured a role that matched both his passion and his financial expectations.
Gareth landed the Director of Product Management role at Twilio with a significant compensation bump from his previous position, at a stable public company with strong total compensation.
“Trust the process, fully commit, stay open to journey ahead”
— Gareth Ouellette, Director of Product Management at Twilio
Gareth Ouellette's Story
This accomplished product leader was getting interviews but was struggling to make it past the final rounds. Gareth is a Director of Product Management at his dream company, Twilio.
He participated in the Product Leader Blueprint program and learned a lot of approaches as a Product Leader, especially in strategy and communication. For many reasons, he separated from his company and started looking for new roles. He gets into many final rounds but the final rounds don't go as well. He gets many 'silver medals' and even gets to #2 out of 2,000 people.
He enrolls in the Intentional Job Search and sees some success. He really commits to the Intentional Job Search Program, jumps into the program and throws himself into refining his narrative and fine-tuning his interviews. He got feedback from coaches on his stories and his interviews until he is confident he can kill it!
Gareth showcases his skills and passion in his latest interviews, builds a custom product strategy leveraging his past experience and learnings from the program, lands two offers, and accepts Twilio - a dream offer - with a massive compensation increase.
If Gareth's story sounds familiar…
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