Every year, PMMs walk into a room full of salespeople and deliver a competitive session that checks every box. Thorough slides. Updated battlecards. Feature comparison grids. A Q&A at the end where nobody asks questions because everyone is just waiting for lunch.
Then the session ends, and nothing changes. Reps still lose to the same competitors. They still freeze when a prospect mentions the alternative. They still pull up the battlecard wrong, or not at all.
Competitive sessions should be designed to transfer confidence.
What Competitive Sessions Usually Look Like
A PMM opens with a competitive overview slide. “There are four main competitors. Let’s go through each one.” They walk through a feature comparison matrix that no rep will ever reference in a live call. They share win/loss data in aggregate. They explain the differentiation in abstract terms (“we’re more AI-native” or “we have deeper integrations”). They end with a leave-behind that’s essentially the slides reformatted as a PDF.
The session is informative and completely useless in the moment a rep needs it.
I built a competitive session at Kustomer for our SKO starting from one question: what do reps need to feel in this room? The answer was confidence. Momentum. The feeling that they could walk into a deal against Zendesk or Salesforce and win it. Everything about the format followed from there.
The Shift: Less Informing, More Hyping
The structure I landed on does four things differently.
Opens with a win story. I pick one competitive deal from the previous quarter. A real one, with a real rep. I bring that rep up to briefly tell the story of how they won. Two minutes. The moment the deal turned. Then I build the session around what made that moment possible.
This works because it’s concrete. “We beat Zendesk at a 1,500-seat deal in Q3 because we could show ROI at the AI layer and they couldn’t” is something a rep can hold onto. It also signals that winning is normal. The opener reframes the room: we are not studying competitors because they are scary. We are studying them because we win.
Runs roleplay. The middle of the session is structured as objection scenarios. I present the top three competitive objections we see in deals — out loud, in character. “Your prospect just said: ‘We’ve been a Zendesk shop for six years and my CTO loves them. Why would I move?’ You have 90 seconds. Go.” Reps pair up. They practice the answer while the room listens. I give feedback in real time.
Being uncomfortable in the session is better than being unprepared in the deal.
Changes the leave-behind. We still do battlecards, but the format changed. What reps walk out with is a one-page competitive quick reference designed for a browser tab. Three sections: the one sentence that reframes the evaluation criteria, the two objections they will definitely hear, and the three proof points that close the comparison down. Something they will actually open in the five minutes before a call.
The PDF battlecard still exists. It lives in the sales portal.
Ends with a prediction. The close of the session is forward-leaning. “Here is where I think the competitive landscape moves in the next two quarters. Here is what we are building that will matter. Here is the one thing I want you to internalize before you leave.” Reps leave feeling briefed on what comes next.
Why Showmanship Is Not Optional
The delivery matters as much as the content.
You are competing for attention in a room full of people who have been in sessions all day. AEs are thinking about their pipeline, their quotas, the deal they need to close before end of quarter. If your session does not grab them in the first five minutes, you have lost them for the rest of it.
Showmanship is about respecting what you are asking of them. You are asking reps to rewire how they handle some of the highest-stakes conversations in their professional lives. That deserves energy. It deserves conviction. It deserves a PMM who has clearly thought hard about what is going to land in this specific room, on this specific day, for this specific team.
I have done this two ways that stuck.
One session I built at Kustomer was themed around The Office. I used clips from the show to anchor each competitive scenario. A Dwight clip before the objection handling drill. A Jim moment to illustrate staying cool under pressure. The room was laughing, and then immediately doing hard roleplay work. The theme made the content land differently because people were leaning in before I even got to the substance.
Another session used basketball plays. I drew up actual plays on a whiteboard the way a coach would in a timeout, assigning each competitive move a play name the team could call in a deal. Instead of “use the positioning flip on the Zendesk objection,” they could just call the play. It converts information into instinct.
What to Actually Build Before the Session
Three things I prepare that never make it into the slides.
- A cheat sheet on the room. Who are the top performers? Which AEs have won competitive deals recently? Which ones are skeptical? I know who I am calling on for roleplay. I know whose win story I am opening with.
- A “so what” for each competitor. One sentence that is the entire point — the one thing I want every rep to be able to say if a prospect asks “how are you different from [X]?” That sentence drives everything else. If I cannot write it cleanly, my positioning is not sharp enough yet.
- A feedback loop. Fifteen minutes after the session, I send a three-question survey. What was most useful? What was missing? What will you actually use? The answers tell me what to fix for next time and what enablement to build in the weeks after, while the momentum is still there.
The Test
A good competitive session passes one test: can a rep, one week later, handle a live competitive objection better than they could before you walked into that room?