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The most expensive mistake in outsourcing your tech stack | Jay Parikh (EVP CoreAI, Microsoft)

In the latest episode of Executive Function, Brett sits down with Jay Parikh, Executive Vice President of CoreAI at Microsoft.

Brett BersonhostJay Parikhguest
Aug 27, 20261h 4mWatch on YouTube ↗

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At a glance

WHAT IT’S REALLY ABOUT

Engineering leadership, speed, and vertical integration lessons from Jay Parikh

  1. Jay Parikh says engineering leadership excellence comes from combining team-building, the right-level vision, an execution cadence, relentless toil reduction, and intentional culture design.
  2. He describes scaling as a physics problem where learning loops get larger and slower, requiring constant rework of operating mechanisms to preserve speed.
  3. He argues that durable speed comes from measuring where time goes (e.g., focus time), removing headwinds, using crawl-walk-run release improvements, and structuring work around small empowered teams.
  4. He explains that customer closeness—including for infrastructure teams—creates purpose and reduces internal delays that otherwise cost market responsiveness.
  5. He outlines how he evaluated “big bets” at Facebook as cross-functional, step-function opportunities, often enabled by vertical integration for efficiency, control, and speed of end-to-end stack change.

IDEAS WORTH REMEMBERING

5 ideas

Excellent engineering leadership is a five-part system, not just “people + tech.”

He frames excellence as building the right team mix, setting a clear but appropriately abstract North Star, creating a measurable execution drumbeat, actively fighting accumulated “toil” that slows delivery, and being intentional about culture as the operating system that enables everything else.

Culture is defined by behaviors and learning loops, not posters or perks.

He describes culture less as slogans or perks and more as the hour-by-hour behaviors and ways of working that determine whether teams keep learning quickly as they get larger and more successful.

Scale naturally slows learning unless leaders actively redesign how work happens.

He argues that as companies scale, the “learning loop” expands and slows, so leaders must fight this by changing operating rhythms, right-sizing meetings, clarifying ownership (e.g., DRIs), and using just-enough process to keep teams effective.

Sustainable speed increases are engineered through mindset + system changes, not impatience alone.

He says durable speed comes from understanding the team’s assumptions, reducing unnecessary blockers, and improving cadence iteratively (crawl-walk-run), not from repeated executive edicts to pull in dates.

Small, empowered teams move fastest—so design for “work charts,” not org charts.

He emphasizes that the fastest teams are small, high-talent-density groups with context and agency, fast escalation paths, and clear ownership—plus leaders willing to correct mismatches in key roles quickly.

WORDS WORTH SAVING

5 quotes

It's never as clean in the inside as it looks from the outside, you know?

— Jay Parikh

For me, for a long time, Brett, I've, like, really focused on this, like, week-over-week progress, right?

— Jay Parikh

If you don't go back and have a culture where you are in some ways, like, fighting allergic, recognizing that this toil can't just infinitely keep accruing or kind of piling up for you, then that just is gonna slow you down, and all sorts of things spiral.

— Jay Parikh

Large teams don't ma- move fast. It's just, like, not possible to me, right?

— Jay Parikh

We spend, I think, uh, having been in lots of different teams, spend a inordinate amount of time arguing A or B.

— Jay Parikh

Five ingredients of engineering leadershipCulture as behaviors and learning loopsWhy organizations slow down at scaleMeasuring execution cadence and “focus time”Small teams, DRIs, escalation, and the “work chart”Customer closeness for infra and product teamsBig bets: step-function impact, cross-functional scope, parallel options, failure tolerance, measurable progress, and vertical integration

SPEAKERS

  • Brett Berson

    host

    Host at First Round Capital who interviews operators and leaders about building companies and teams.

  • Jay Parikh

    guest

    EVP, CoreAI at Microsoft and former Facebook engineering/infrastructure leader.

High quality AI-generated summary created from speaker-labeled transcript.

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