Competitive War Gaming

Assign teams to deeply understand competitors, then present findings in a competitive summit

Annie Pearl
Behind the scenes of Calendly's rapid growth

Competitive War Gaming

"On some sort of time interval, sometimes it's been quarterly, we'll have assigned people into groups for the quarter to own a competitor. And their job is to essentially spend a lot of time immersing themselves into the product of the competitor, really trying to think through the lens of, do a SWAT analysis, really try to think through the lens of where's this competitor going and how Calendly only think about that." - Annie Pearl

What It Is

Competitive War Gaming is a structured process where cross-functional groups are assigned to "own" specific competitors, deeply research them over a quarter, and then present their findings in a competitive summit (the "war gaming day").

The approach solves the problem of competitive intelligence being either nobody's job or everybody's job. Instead of expecting every PM to track every competitor (impractical) or having no one track competitors (dangerous), the work is distributed and then consolidated.

How It Works

The Quarterly Cycle:

Phase 1: Assignment (Week 1)

  • Identify key competitors to track (3-6 typically)
  • Form cross-functional groups (2-4 people each)
  • Each group is assigned one competitor to "own"

Phase 2: Immersion (Weeks 2-10)

  • Groups deeply use the competitor's product
  • Document features, pricing, positioning
  • Conduct SWOT analysis
  • Research company strategy, funding, hiring signals
  • Analyze: Where is this competitor going?

Phase 3: War Gaming Day (Week 11-12)

  • All groups present their findings
  • Include prizes and gamification
  • Structured Q&A and discussion
  • Capture insights for strategic planning

What Each Team Produces:

Deliverable Purpose
Product deep-dive What can they do? How does it work?
SWOT analysis Strengths, weaknesses, opportunities, threats
Strategic projection Where are they headed? What bets are they making?
Implications for us What should we do differently?

How to Apply It

  1. Select competitors strategically:

    • Direct competitors (obvious)
    • Emerging players (less obvious)
    • Adjacent products that could expand (important)
    • Platform plays that could commoditize you (critical)

  2. Form diverse groups:

    • Mix PMs, designers, engineers, go-to-market
    • Different perspectives yield richer analysis
    • Groups of 2-4 keep work distributed

  3. Provide structure without rigidity:

    • Give a template/framework for analysis
    • But let groups adapt to their competitor
    • The best insights often come from unexpected angles

  4. Make war gaming day engaging:

    • Time-boxed presentations
    • Prizes for best insights (not just best presentation)
    • Capture action items explicitly
    • Make it fun—this is collective learning

  5. Feed insights back to strategy:

    • Don't let the work disappear
    • Update competitive positioning docs
    • Inform roadmap priorities
    • Revisit at next planning cycle

When to Use It

  • When your market has active competitors worth tracking
  • When competitive knowledge is inconsistent across the team
  • When you want to build strategic thinking capability
  • When decisions are being made without competitive context

Cadence recommendations:

  • Quarterly: Fast-moving markets
  • Semi-annually: Stable markets
  • Ad-hoc: When major competitive changes occur

Source

  • Guest: Annie Pearl
  • Episode: "Behind the scenes of Calendly's rapid growth"
  • Key Discussion: (00:48:12) - Describing competitive war gaming process
  • YouTube: Watch on YouTube

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