Our AI-ML PM Masterclass, PM Community Meetup, growth insights for Sr Product Leaders, hot jobs from my network & more!

Author

Priyanka Upadhyay
January 08, 2026

Piper & I enjoying redwood forest trails

👋 If you’re new to this newsletter - Welcome!

What’s new from Coach Pri?

As we get into 2026, I’ve been thinking less about goals 🎯 — and more about where I can create the most meaningful impact. 📈

For 2026, I’m anchoring my decisions around three words: Energy, Innovation, and Unlearning. They’ve become a filter for how I spend my time and who I choose to work with.

That reflection led me to rethink this newsletter as well. Going forward, I’ll be sharing insights, strategies, and resources to help with the most pressing challenges I see senior product leaders navigating today —

  • Operating in ambiguity,

  • Making high-stakes tradeoffs,

  • Stepping into a leadership role without the right tools, skills & resources,

  • Influencing without authority, and many more!

    I’m intentionally narrowing my focus in 2026 - to dedicate my time and energy to experienced product leaders, where I consistently see the fastest and deepest impact.

This aligns with the mission I set out for 2.5 years ago when I started Product-with-Pri…

“Enable product managers to grow into senior leadership, so more women and diverse voices are represented at the top”!

If this more focused format feels more useful than my earlier ones, feel free to reply with “better” — I’d genuinely appreciate the signal.

P.S. - If you DO find this newsletter useful, could you please move it out of your Promotions folder/tab in Google, and into your inbox, so you don’t miss any upcoming masterclasses, events, or insights? Thank you!

Upcoming Events

I’m hosting an AI-ML PM Interview Masterclass on Friday, Jan 23, focused on how senior AI PMs are actually evaluated — beyond demos, buzzwords, or surface-level model knowledge.

This session is designed for Senior to Director-level PMs preparing for AI/ML roles who want to clearly articulate judgment, tradeoffs, and end-to-end product thinking in interviews.

Two ways to join:

  • Virtual - Friday Jan 23rd (12–1 pm PT) — Free
    We’ll cover:

    • How AI PM interviews differ at senior levels

    • What interviewers listen for when assessing judgment and clarity

    • A few key strategies to stand out in AI PM Interviews

    • BONUS 🎁: My AI PM Interview Question Bank for practice

      👉 Register here

  • In-Person - Friday Jan 23rd (5:30–8 pm PT, San Jose) — $50
    A deeper, interactive session with:

    • Live discussion, Q & A and real interview examples

    • Key Strategies to stand out as a Sr AI PM in interviews, and on-the job!

    • Networking with other senior level PMs + refreshments

    • Exclusive insights from a client who recently landed a Sr. AI PM job!

    • BONUS 🎁: My custom storytelling framework/template with examples

      👉 Register here before we’re full!

P.S. If you’re local and can make it, I recommend the in-person experience.

PM Insight of the week

💪 Decision ownership matters more than scope ownership.

In lean, AI-driven teams, senior PMs are valued less for the size of their roadmap and more for the quality of decisions they personally own — especially under ambiguity and incomplete data.

How this shows up on the job:

If you want to show up as a strong product leader, don’t wait for perfect clarity. Make decisions with the data you have, name the tradeoffs out loud, and help the team move forward.

Waiting for full certainty often costs momentum — and influence. I see this pattern often, especially with women. A familiar example? Re-reading and re-writing the same email (sometimes with multiple ChatGPT iterations 😅) before hitting send.

Ask yourself: What would change if I trusted my judgment a bit sooner? Or, is this decision worth fussing over?

How this shows up in interviews:

Interviewers listen for the same signal: the decisions you owned, trade-offs you made, how you rallied others & aligned them to your vision, and how your judgment shaped outcomes. Leading only with scope or execution can undersell your impact.

Who’s hiring (job posts from my network)

Curated list of live roles from hiring managers & recruiters in my network:

  • Quizlet – Hiring a Sr. PM, Search & Recommendations → HM Post

  • Opportun (Fintech) – Hiring a Principa PM, Gen AI adoption → HM Post

  • Atlassian – Hiring a Principal PM, Growth & Engagement → Recruiter’s Post

  • Amazon – Hiring a Principal PM, AWS Security → Recruiter Post

  • Gusto - Hiring a Principal PM, Gusto Pro, focused on payroll/accounting for small businesses → Linkedin Post

  • NBC Universal – Hiring a Principal PM, Ads & Experience, NYC → HM Post

  • Measured – Hiring a Principal AI PM, Austin, TX → HM Post

  • Twilio – Hiring a Sr. Principal PM, AI - Remote → Linkedin Post

  • Disney – Hiring a Principal PM, Disney+ → Linkedin Post

  • Microsoft –

    • Hiring a Principal PM, Core AI Platforms → HM Post

    • Hiring a Principal PM, Ads Measurement, Seattle → HM Post

    • Hiring a Principal PM, AI, Developer Experience & Platform Reliability → HM Post

    📍 More roles? Check out trueup.io/jobs.

Ready to operate at the next level in 2026?

If the trends above resonated — and you’re feeling the pressure to operate at a higher level, whether in your current role or your next one — here’s the most impactful way to work with me right now:

A VIRTUAL, 8-week group coaching experience for Senior, Principal, and Director-level PMs who want to grow with clarity and confidence. Limited to 10 spots only.

This is not a one-size-fits-all, cookie-cutter program.

PM Level-Up is a high-touch coaching experience with 1:1 coaching, small-group sessions, community support from other Senior Product Leaders, mindset and wellness work, and guest AMAs with PM and AI leaders — designed for senior product leaders who want meaningful, practical growth.

This is for experienced product leaders who want to strengthen AI PM skills for real-world leadership and interviews, prepare for promotion, expanded scope, or a thoughtful career move, or strengthen their on-the-job skills, and show up as impactful leaders.

I’ve worked with 40+ Senior Product Leaders (Sr PM → Director) at top tech companies across the U.S. (Amazon, Netflix, Stripe, Google, Meta, Adobe, Cisco, and more), and several high growth startups, who’ve expanded scope, moved to the next level, strengthened compensation, and — most importantly — built confidence in showing up as the leaders they want to be.

  1. Not ready to work with me yet ? I got you covered!

  • If you want a clearer view of your current strengths and growth areas, I’ve created a PM Skills Assessment Test (aka, an in-depth quiz 😉 ) used by experienced product leaders to assess judgment, product thinking, and leadership fundamentals.

  • It reflects real on-the-job PM skills — and often surfaces where strong PMs struggle to translate that work into influence, leadership presence, or next-level roles.

One of the patterns I see most often with strong senior PMs is this: growth doesn’t stall because of lack of ability — it stalls because decisions get deferred.

Whether it’s stepping into bigger scope, sharpening how you show up as a leader, or preparing for what’s next, momentum usually comes from making a clear call and moving forward — not waiting for perfect timing.

If 2026 is a year where you want to operate with more clarity, confidence, and intention, this is a good moment to act on that.

Here’s to a year of thoughtful decisions and meaningful impact,
— Coach Pri 💛