Engineering Leadership Interviews in the AI Era

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Engineering Leadership Interviews in the AI Era

Hosted by Sherveen Mashayekhi

Thu, Oct 23, 2025

9:00 PM UTC (30 minutes)

Virtual (Zoom)

Free to join

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AI Fluency Bootcamp

Sherveen Mashayekhi

View syllabus

Thu, Oct 23, 2025

9:00 PM UTC (30 minutes)

Virtual (Zoom)

Free to join

Invite your network

Go deeper with a course

AI Fluency Bootcamp

Sherveen Mashayekhi

View syllabus

What you'll learn

Prove you can lead an AI-era engineering org

It's not just familiarity with Cursor. So much has changed in team design, platform architecture, and AI tooling.

Demonstrate your executive presence and leadership

It's the most competitive time in engineering leadership ever. You have to demonstrate seniority and cross-fx care.

Storytelling to prove your readiness for the future

So much of engineering leadership is now about upskilling teams, building new platforms, and being future-forward.

Why this topic matters

Director, VP, and C-level engineering leadership interviews are hard. You have to showcase the right combination of soft skills, technical savvy, cross-functional capability -- now, with added AI modalities to de-risk an engineering org's legacy code + behavior, and a more sensitive set of capital markets for R&D. Let's dig in!

You'll learn from

Sherveen Mashayekhi

Founder & CEO @ Free Agency, AI Product Leader & Investor

Sherveen has been an AI product leader and founder in tech for over a decade, but more importantly, is a long-time obsessive about startups.

He's a first adopter of AI tools and sits in exclusive circles of founders + venture capitalists building the cutting edge of applied AI products. As the founder and CEO of Free Agency (backed by investors like Maveron, Bloomberg Beta, Kevin Durant, and Kygo), he now helps tech professionals navigate the modern hiring landscape.

Since 2019, clients of Free Agency have won over $400M in job offers and landed at top companies like OpenAI, Amazon, American Express, Stripe, YouTube, Netflix, and hundreds more.

He's the host of three shows + podcasts about early stage tech: The Feedback Loop, Three Course Founders, and The Sherveen Show, where he talks multiple times a week with the most exciting technologists, CEOs, and investors building the future.

See more: https://youtube.com/@sherveenshow

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