Do you have to be in pain to put Win/Loss Analysis to good use?

I’d say no, not at all.

I recently looked over the list of small and mid-size technology companies we engaged with this year. For more than half, it was opportunity—not pain—that motivated their interest in Win/Loss Analysis.

These companies want to play better offense, building on their success by pushing into a new frontier. That new frontier can be literal, new market territory, or figurative, a new level of sales and marketing performance in the current markets.

3 Types of New Frontier Opportunities

These three opportunities were the most common motivators I heard this year:

  • Faster expansion into a new market. Here the goal is better insight into a new type of buyer, whether it’s a new vertical, market segment, or geography. In a recent case, for a startup expanding from healthcare into legal, progress was being slowed by uncertainty and internal debate about pain points and differentiation in the new vertical. But individual visions and anecdotes were no match for buyer interviews and a Win/Loss Analysis of that data.
  • Finding competitive advantage. Factual, up-to-date competitive insight is one of the most common reasons companies consider win/loss, and this year was no different. In these cases, we talk about opportunities to take market share from weak competitors — a CRP to cannibalize their customer base or search advertising to pull buyers at new accounts into bakeoffs. The converse presents another opportunity — to shore up against a stronger competitor and the threat of lost revenue.
  • Accelerating in the current market. Recently, a sales leader told me he wants to “win deals faster” in order to win more with the same setup and reduce the cost of sale. For companies like this one, accelerating deals is a bigger priority than improving win rate; their win rates are already “exceptionally high.”

Begin With The Best

If there are opportunities like these in your business, remember a good Win/Loss Analysis is deep and focused. Twenty buyer interviews is a good baseline size in most cases. But interviewing twenty buyers in the current market won’t also yield insight for faster growth in a new one.

My advice is to invest six weeks to complete a Win/Loss Analysis of the most attractive opportunity, then move to the next best.

As a former product manager, I find this is an appealing design for a Win/Loss program because it spreads and balances the opportunities around the lean agile Build-Measure-Learn feedback loop. While marketing, sales, and product Build on the learnings about one opportunity, the preceding one’s impact is being Measured, and we’re using win/loss to Learn about the next one.

How do you want to play better offense next year?