We’ve spent some time on our wins and losses–and took action! Some updates to share that you may find useful or even exciting:

1. Skyp launched an MCP server so you can use Skyp right from Claude–the first of its kind. We won an Apollo hackathon with it.

2. Signals partnership launched with BirdDog to find prospects based on what actually leads to conversions.

3. LinkedIn outreach is in beta and I’ve already gotten several meetings from our thoughtful, targeted approach to this channel.

If it’s been a while, we’d love to show you. 👇️ 

Onto the newsletter!

Almost every sales organization does some version of win/loss analysis. Almost none of them change their behavior because of it.

Early on these are ad hoc. Two founders talking about why Tuesday’s demo didn’t convert. Or a founder talking with her first rep about where things went wrong.

Blame might be thrown. It might get heated. But the best organizations learn something and immediately change things–a new qualification before a demo, or a better ask at the end of the demo. Maybe a new pricing/package combo.

Early on, action is the default–almost to a fault.

Later, win/loss takes on structure. And becomes a farce. A report gets written, the findings get presented in a quarterly business review, and then the document lives in a shared folder that nobody opens again.

Meanwhile the same deals are being lost for the same reasons. The same objections are landing the same way. The same competitors are winning in the same situations.

Why most programs fail

The first failure is in who does the interviews.

When a sales rep conducts their own win/loss interviews, the answers they get are polite. Buyers don't tell the person who just lost their deal that the rep came across as unprepared, or that the pricing felt arbitrary, or that a competitor's champion did a better job navigating their internal politics. They say something reasonable and move on.

The same problem applies when interviews are conducted by customer success or account management. The relationship comes first. The truth comes second.

Real win/loss data requires independence. Someone with no stake in the outcome, no ongoing relationship to protect, and no incentive to hear a particular answer.

When you’re midsized, founders can be great for this. Prospects are willing to talk to them, and they are genuinely interested. As you grow, replicating this connection is key.

The second failure is in what gets asked.

Most win/loss interviews focus on the product — features, pricing, integrations, roadmap. These are easy to ask about and easy to report on. They're also usually not why deals are won or lost.

Deals are won or lost because of the sales process, the internal dynamics of the buying committee, the way the champion was or wasn't equipped to sell internally, and the quality of the relationship between the rep and the key stakeholders. These things are harder to ask about. They're also far more actionable.

What the interviews should actually uncover

The questions that produce useful data aren't the obvious ones.

"Why did you choose them over us?" gets you the official answer, which is usually about features or price.

Instead: "Walk me through the internal conversation. Who was involved? What were the main concerns? How did those concerns get resolved?"

"What could we have done differently?" earns a polite and diplomatic response.

Instead: "Was there a moment in the process where things shifted? What happened before that moment and after it?"

"How did you find the pricing?" will get a repeat of their last negotiating position, not the real view.

Instead: "When pricing came up internally, how did it get framed? What was the comparison point people were using?"

The goal isn't to get feedback. It's to reconstruct the buying process — to understand what the buyer was actually experiencing at each stage, what they needed that they did or didn't get, and where the deal was really won or lost.

The analysis that actually matters

Once you have the interviews, the temptation is to look for patterns in the product feedback. Competitors are beating you on feature X. Buyers want integration Y. Pricing structure Z is creating friction.

Some of that is real and worth acting on.

But the patterns that change behavior are the ones about the sales process itself.

Which reps are winning deals that others are losing and why? Not because of territory or account quality, but because of what they do differently in discovery, in champion development, in late-stage navigation?

Which deal stages are losing the most opportunities? What's happening there that isn't visible in the CRM?

Which buyer personas are converting at different rates? What does that tell you about where your ICP is actually sharp and where it's aspirational?

Which competitors are beating you in which situations? A competitor that wins when they get in early is a different problem than one that wins in a bake-off. I don’t take it personally if we arrive late to the party and don’t get picked. But if we were there at the same time–or first–that is alarming and demands attention.

These patterns don't come from a survey. They come from qualitative interviews done by someone without an axe to grind.

What to do with your win/loss learnings

It isn’t enough for the salesperson or the founder to figure out what went wrong. You have to change behavior. Three ideas, in order of difficulty.

Make sure reps are coached on the pitfalls and patterns to avoid. A lot of losses happen in early meetings–expectation setting, positioning, and even who to involve in the buying process. Make sure reps know the updated playbook. This is easy.

Update your messaging. This is far easier than updating the product or building new features. Salesforce exemplifies this–launching “headless CRM” without actually shipping a damned thing, and renaming the AppExchange “AgentExchange”. Pure messaging that will buy them 2-3 years while their product team catches up. This is still pretty easy, but takes coordination across marketing and sales.

The biggest lift is to update your strategy. Markets change and where you had PMF your win/loss may show that you’ve lost it. Should you refocus on segments where you consistently win? Niche down? Or address the losses with product? This can be harder and riskier–don’t do it too often.

Painful but necessary

Julian and I do a win/loss analysis on every deal. I personally can’t stand it, but know the medicine is good for me. There’s no blame–just curiosity. This is the hardest part.

We’ve made a lot of changes as a result, some small some big. In those three buckets:

1. Sales rep coaching. I’m the rep, so I’ve learned. This was probably the hardest for me, personally. We run our early sales meetings differently (no demos in the first meeting anymore) and I manage expectations better as we’ve learned from where we’ve lost.

2. Messaging. We just updated our messaging across the board, to move beyond founder-led-sales where we had PMF but think that Claude Code has won out, and moved upmarket. That included updating packaging and more.

3. Our strategy reflects the updated messaging (really, vice versa). By focusing on slightly larger teams and companies we’re leaning into what’s working, and leaning away from the promising sales conversations that led to a loss. At the time it wasn’t predictable–but now we see the pattern, and have heard it in win/loss discussions. Rather than fight it directly, we’ll go with the flow.

The more you can get honest answers from your win/loss program, and actually change behavior, the more likely you are to both find and maintain PMF. And the faster you will grow.