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2 Tips + 2 Takeaways From Our Win/Loss Webinar with Nick Siddoway and Brad Rosen

For the third installment of our new Win/Loss Wednesdays series, we had the pleasure of chatting with Brad Rosen, President at Sales Assembly, and Nick Siddoway, President & CRO at TruVoice from Corporate Visions.


By the end of the conversation — which was primarily focused on using win/loss insights to improve sales team performance — Nick and Brad had shared several tips and takeaways with the audience.

Our two favorite tips:

  • If win/loss is a new initiative at your company, start by sharing insights from wins and no decisions – hold off on losses.
  • Don’t bring recommendations to your executive team unless they’re based on feedback from at least 15% of your deal universe.

Our two favorite takeaways:

  • Better to have the best player than the best hand.
  • Price is always a factor, but it’s seldom THE factor.

Tip: If win/loss is a new initiative at your company, start by sharing insights from wins and no decisions – hold off on losses.

Win/loss doesn’t work unless your sales reps have bought into it. If they don’t change their behavior in the ways you need them to, the program is pointless.

One reason it can be difficult to earn buy-in is because, at first, many sales reps are intimidated by win/loss – they’re afraid that they’ll be called out for losing deals they should have won.

Nick and Brad suggest easing this fear by kicking off your win/loss program with insights exclusively from won deals and no decisions. Once the sales team realizes that win/loss is their friend – not their foe – you can begin sharing insights from lost deals, too.

Tip: Don’t bring recommendations to your executive team unless they’re based on feedback from at least 15% of your deal universe.

Your “deal universe” is comprised of all the buyers who could potentially give you actionable win/loss insights. Typically, these are buyers who have made a purchase decision in the past 30-120 days.

In Nick’s experience, when you bring recommendations to the executive team, at least one person in the room will push back and ask, “How big was your sample size?”

To avoid losing your credibility, Nick says all recommendations should be based on feedback from at least 15% of your deal universe – if not more.

Takeaway: Better to have the best player than the best hand.

A 2009 study of 103 million online poker games found that the player with the best hand only wins 12% of the time, which suggests that success in poker is 88% skill and 12% luck.

Nick cited this study during the webinar to make a point: Even if a buyer thinks your product is inferior to the competition – even if you’re not holding the best hand at the table – you can still win the deal on the merits of your sales experience – you can still win the game with skill. In fact, it’s often better to have a skilled seller than a perfect product.

What this means for you: Do you want your product team to use your win/loss insights to build cool new features? Of course – but that takes a long time, and the impact won’t necessarily be huge. You can get quick wins for your program today by using your insights to upskill sellers.

Takeaway: Price is always a factor, but it’s seldom THE factor.

If you’ve ever bought software, you know how uncomfortable it is when the seller who lost the deal asks you why you went with their competitor.

It’s so uncomfortable, in fact, that many buyers will lie and say “I made my decision based on price” just because it’s the easiest and least awkward way to end the conversation.

But as Brad pointed out during the webinar – and as he often reminds the sales reps he coaches – it’s never really about price.

Do buyers take price into consideration? Of course. But if a seller does their job – if they clearly demonstrate the ROI of the product they’re selling – then the buyer will most likely feel OK about whatever price they’re quoted. They’ll feel motivated to find the necessary budget.

In other words: When a buyer says “I made my decision based on price,” what they’re really saying is “I didn’t see enough value in your product to justify the price."

It’s not about price – it’s about a sales experience that showcases value effectively.

What this means for you: When a sales rep tells you they lost a deal because of price, take it with a grain of salt. Try to get on the phone with the buyer and dig deeper into their decision-making process. You’ll probably find that the seller made mistakes throughout the sales process – mistakes that everyone on the team can learn from.

Every day is Win/Loss Wednesday

Click here to watch the recording of our conversation with Nick and Brad. Click here to watch our webinar with Scott Frost, where he shared tips for getting your executive team to buy into win/loss. Click here to watch our webinar with Jayde Phillips, where she shared tips for sharing win/loss insights with stakeholders across your company.

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Conor Bond
Conor Bond is on the marketing team at Crayon. If, for whatever reason, you were to rip his headphones off his head and put them on yourself, you’d probably hear Weakened Friends or Charli XCX.
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