How to be friends with sales, even as a loser PMM

Ok we’re not losers, but it really depends on your relationship with sales, especially in a small and mighty team

Often, head to head, marketing/product marketing will always lose influence against sales because they are the “machine a saucisse” (sausage-maker) of the company

And if you already lack influence, huge executive decisions like positioning and getting their input can be challenging

So today, we’re tackling the subject, especially if you’re in a new organization, trying to befriend with the cool kids 😎

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Can you be friends with Sales or are they too cool? 🤔

Sales in tech is often seen as the coolest role. Every time Zach talks about his past career, I get lost in dreaming about how cool it must have been

Chilling with the big dawgs 🐶, crushing cans of Red Bulls and Adderalls to reach quotas is SO MUCH COOLER than changing the color of the presentation deck for our upcoming webinar with 14 registrants

But to be honest, let’s just say that the roles are so different, but understanding sales priority explains a lot of why you can’t or don’t have access to their feedback yet, it starts with influence

Here are a few things Zach made us understand in 3 seasons:

Sales are driven by quota

This might sound obvious, but it’s more than just hitting numbers—it’s their whole mindset. Sales live and breathe that next deal, and everything else is secondary. As a PMM, if you're not speaking the language of "how this will help you close," it can feel like you're getting sidelined. Why? Because, quite frankly, everything that isn’t directly connected to quota is noise.

You don’t have to be a sales guru to get access to their insights, but you do need to be smart about how you approach them.

Bring a specific outcome

Salespeople don’t want vague feedback or endless research. They want something actionable. Frame the conversation around something concrete—like how to handle specific objections you've heard during win-loss analysis, or offering messaging tweaks that might give them an edge in negotiations. Show that you're offering something they can use to get closer to quota.

Approach It as a side project:

Rather than asking for big chunks of their time or a deep-dive review of your positioning work, make it easy for them to engage.

Keep it short, focus on the essentials, and build a relationship slowly. Salespeople love quick wins—so if you can provide one with minimal effort on their part, they’re more likely to keep the feedback loop open.

We’re all about sales enablement…as long as you’re not asking us to write another slide deck 🙄

Building a DIY Win-Loss program that doesn’t explode your todo list

1. Prioritize one key problem to solve

You already have a full plate, so it's essential to focus on the areas that can drive the most impact. Prioritize one key problem you want to solve. It can be pricing issues, product feature gaps, or sales process misalignment.

2. Start with 5 interviews

You don’t need to speak to every lost deal. Instead, focus on a small sample that can still provide significant insights. Start with just 5 interviews—this way, it’s manageable and doesn’t feel like another full-time project.

3. Ask targeted questions

Design a handful of questions that get straight to the core of why the deal was lost. This keeps the process efficient, and you’re still able to gather powerful insights. Always go back to the objective you have in mind.

4. Create a basic reporting template:

Whether it’s Google Sheets or Notion, use something you and your team are familiar with and categorize feedback without overcomplicating the process.

5. Share actionable insights:

Focus on 2-3 insights that sales can leverage to get quick wins that can influence changes in the sales process or product features. Stick to a schedule whether on email updates or regular meetings (2x a week with key sales members work well)

6. Repeat without overcommitting:

Set a sustainable cadence that works with your workload. Even if you conduct win-loss interviews once every quarter, the insights can still provide significant influence over time. If you conduct win-loss interviews once every quarter, it’s manageable and still feeds a ton of insights.

Now, go make some friends! 🧑🏽‍🤝‍👩🏻‍

To paraphrase my Mom when I was in 6th grade: “Common, go make some friends!“

Unfortunately, it never happened because I was already in line to be in B2B SaaS and WORSE, a theater kid 😩.

But you don’t have to be.

Just follow these guardrails to make sure that:

1. You can help sales crush it

2. You stay aware of the following guardrails

The guardrails:

Align on your win-loss analysis purpose

Build trust through listening, not judging

Work with the top sales reps

Offer to partner in sales calls

Celebrate wins, not just losses

Matthew Reeves is breaking down exactly how to identify the biggest problems and create a win-loss program that—won’t break the bank & won’t get overwhelming—in this week’s episode. If you’re tired of being the uncool PMM, time to impress the cool kids.

🎙Featured Episode:
Become Sales Best Friend with Win-Loss Analysis w/ Matthew Reeves

Matthew Reeves, CEO and co-founder of GoldPan, runs a win-loss analysis agency. In this episode, he’s showing us:

→How to build rapport with sales teams

→The complexities of positioning and messaging

→Why you need both wins and losses for good research. 

→Why information overload kills sales. 

→The nuanced value of churn analysis. 

Hear also the very unique take of Matthew that marketers are not even marketers.

Check the episode here

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