All of our Strategy articles

From Flagship Back to Fledgling: Lessons on Going Multi-Product From an Early Stripe PM

In this exclusive interview, Tara Seshan shares nine lessons from her playbooks for going multi-product, drawing on examples from both Stripe and Watershed.

How to Take Bigger, Bolder Product Bets — Lessons from Slack’s Chief Product Officer

Seasoned product leader and Slack’s CPO Noah Desai Weiss shares the three-step framework he leans on to make quality product decisions with just the right amount of risk.

How Talent Teams Can Better Weather Boom-and-Bust Cycles — Advice from Two Decades at Gem, Facebook, and Robinhood

Richard Cho has led talent acquisition teams at large tech firms for the better part of two decades. He’s collected the lessons he’s learned from operating in both hiring booms and busts, offering a thoughtful guide on how startup talent teams can do more — with less.

How to Sell Your Startup: The Complete Guide to Running an M&A Process as a Founder

As a repeat founder, Daniel Debow has successfully sold three different startups. He reveals his no-nonsense playbook for other startup founders on how to run an M&A process from top to bottom.

Annual Planning in Uncertain Times: 6 Tactics for Rethinking Your Company’s End-of-Year Exercise

We’ve combed the extensive Review archives for a timely roundup of the most unique advice for end-of-year strategic planning. Leaders like Lenny Rachitsky, Nels Gilbreth, Jeff Lawson, Annie Duke, Ravi Mehta and more share the inventive frameworks they lean on for this annual exercise.

Grit or Quit? Tactical Advice for Founders Facing Tough Company Building Decisions

Quitting is an underrated startup skill, says decision science expert, bestselling author, and former poker pro Annie Duke. She unpacks the psychology behind why it’s so hard to walk away, sharing tactical advice for all the forks in the road.

How Product Strategy Fails in the Real World — What to Avoid When Building Highly-Technical Products

Why does strategy tend to stall when the rubber hits the road? Nate Stewart, Chief Product Officer of Cockroach Labs, shares an essential guide for creating a resilient strategy that’s still standing next year.

The Tactical Guide to Making Better Decisions When Starting and Scaling Companies

The First Round team has been lucky to work with retired poker player and decision-making expert Annie Duke in a special capacity these past few years. Here, we open-source some of the advice she gives to help founders face down uncertainty and make better decisions.

23 Tactical Company Building Lessons, Learned From Scaling Stripe & Notion

From Stripe to Notion, Cristina Cordova has worked on some of the biggest products in tech. She shares tactical tidbits on what she’s learned about scaling companies and shaping your career.

Great Startups Deserve Great Brands — Build a Strong Foundation by Avoiding These Mistakes

After working with hundreds of startups on brand strategy, Arielle Jackson shares the most common early marketing missteps that founders make. From how to articulate your product benefit and clarify your company's purpose, to tips for infusing your brand with personality and making your launch announcement.