In this episode, I’m joined by two tech veterans, Garrett Rice (former Apple) and Philippe Cailloux (former Head of Product Design at Adobe), co-founders of Callings.ai—a platform that’s rethinking how we search for jobs in the AI era. We dive into how the traditional job-hunting process is broken, what’s wrong with the resume as we know it, and how AI can help job seekers know themselves better, stand out, and land more meaningful work.

💡 Key Takeaways:

• Why resumes and job portals are built for companies, not candidates—and how that’s failing job seekers.

• The origin story of Callings.ai and how Garrett & Philippe used their own job hunt frustration to build a new solution.

• How AI can help users reflect, self-brand, and generate tailored applications at scale.

• The importance of personal intention and identity in an increasingly automated hiring world.

• The philosophical and practical shift from “spray and pray” to focused, purposeful job searching.

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🎓 What You’ll Learn:

• How AI is changing the job search process

• The flaws of applicant tracking systems (ATS)

• How to use personal branding to stand out

• Why self-awareness matters more than ever

• The role of LLMs in reimagining career platforms

👤 About the Guests:

Garrett Rice is a former Apple executive and startup operator with deep expertise in technology, product, and business building. Garrett is a

leader with a 25-year record of shipping innovative products, developing meaningful partnerships, designing effective processes and leading dynamic teams. Experience with startups, medium and large companies. Love building things and solving problems to make customers happy and companies better.

https://www.linkedin.com/in/garrettrice/

Philippe Cailloux has 20+ Years of Experience, he engaged in emerging technology product strategy and design, leading teams to develop products appreciated by a global user base (hundreds of millions).

He has led product design at Adobe and several other companies, and brings a unique lens to merging user-centric design with cutting-edge AI.

https://www.linkedin.com/in/cailloux/

Together, they co-founded Callings.ai, a platform focused on empowering job seekers—not employers—with AI-driven tools to navigate the modern hiring landscape.

https://callings.ai/

Episode Highlights:

⏱️ [00:04:20] – Why traditional job search tools ignore the candidate’s experience

⏱️ [00:08:40] – Building tools out of frustration: the founding story of Callings.ai

⏱️ [00:16:00] – Resume ≠ identity: how AI helps uncover the real value behind your past roles

⏱️ [00:27:30] – The “My Insights” feature and how AI personalizes the career journey

⏱️ [00:34:50] – LLMs as enablers: using tech to accelerate self-discovery, not replace it

⏱️ [00:45:00] – The role of purpose, personal branding, and the future of work

⏱️ [01:03:00] – Will AI lead to one-person unicorns? The myth, the reality, and the nuance