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How to be friends with sales, even as a loser PMM
BOOM! Roasted. Ok you're not really a loser đ
The Loserâs Circle
Ok weâre 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 âmachine a saucisseâ (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, weâre tackling the subject, especially if youâre in a new organization, trying to befriend with the cool kids đ
Welcome to the next episode of Dying 4 Influence. The weekly newsletter for misunderstood B2B product marketers.
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Can you be friends with Sales or are they too cool? đ€
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 đ¶, 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, letâs just say that the roles are so different, but understanding sales priority explains a lot of why you canât or donât 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 itâs more than just hitting numbersâitâs 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 isnât directly connected to quota is noise.
You donât 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 donât want vague feedback or endless research. They want something actionable. Frame the conversation around something concreteâlike 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 winsâso if you can provide one with minimal effort on their part, theyâre more likely to keep the feedback loop open.
Weâre all about sales enablementâŠas long as youâre not asking us to write another slide deck đ
I swear, I WILL END UP LOSING IT
Building a DIY Win-Loss program that doesnât 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 donât need to speak to every lost deal. Instead, focus on a small sample that can still provide significant insights. Start with just 5 interviewsâthis way, itâs manageable and doesnât 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 youâre still able to gather powerful insights. Always go back to the objective you have in mind.
4. Create a basic reporting template:
Whether itâs 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, itâs manageable and still feeds a ton of insights.
Now, go make some friends! đ§đœâđ€âđ©đ»â
To paraphrase my Mom when I was in 6th grade: âCommon, go make some friends!â
Unfortunately, it never happened because I was already in line to be in B2B SaaS and WORSE, a theater kid đ©.
But you donât have to be.
Just follow these guardrails to make sure that:
You can help sales crush it
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 thatâwonât break the bank & wonât get overwhelmingâin this weekâs episode. If youâre tired of being the uncool PMM, time to impress the cool kids.
đFeatured Episode:
Become Sales Best Friend with Win-Loss Analysis w/ Matthew Reeves
Episode 35 with Matthew Reeves
Matthew Reeves, CEO and co-founder of GoldPan, runs a win-loss analysis agency. In this episode, heâs showing us:
âHow to build rapport with sales teams
âThe complexities of positioning and messaging
âWhy you need both wins and losses for good research.
âWhy information overload kills sales.
âThe 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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Thatâs all weâve got for this week. If we made you smile (or did that weird thing when you donât fully laugh but air goes out of your nose), please pay it back by telling us on the 2-sec survey below đ
See you next Friday,
Gab, Eric, and Zach
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