I spent three weeks building a sales play for selling into the financial services vertical. I researched the industry. I identified pain points. I built buyer personas. I created talk tracks. I designed discovery questions specific to financial services buyers.
I presented it to the sales team. They said it looked great. I put it in our shared drive. I sent the link in Slack.
Three months later, I asked reps how the financial services play was working. They looked at me blankly. "What play?"
I checked the Google Doc. Three views. Two of them were me.
That failure taught me what I should have known from the start: Sales plays fail when you build them in isolation. They succeed when you build them with the people who have to use them.
Why Most Sales Plays Sit Unused
The financial services play failed for the same reason most sales plays fail: I built it based on what I thought reps needed instead of asking what would actually help them sell.
I made assumptions:
- Reps needed industry-specific talk tracks (they didn't—they needed help identifying qualified prospects)
- Reps needed detailed buyer personas (they didn't—they already knew who to sell to)
- Reps needed discovery questions (they didn't—they needed objection responses for common pushback)
The play I built solved problems reps didn't have. Meanwhile, the actual problems they faced in financial services deals—long sales cycles, procurement bureaucracy, security objections—went unaddressed.
I learned this when I sat in on a financial services deal six months later. The rep was getting hammered on security compliance questions. After the call, I asked: "Did you use the sales play?"
He said: "I looked at it once. It had great stuff about the industry, but nothing about how to handle these security objections. So I just figured it out myself."
That's the moment I realized: reps don't need industry context. They need scripts for the moments when they get stuck.
What a Sales Play Actually Does
Most PMMs think sales plays are strategic documents. We include:
- Market context
- Buyer personas
- Value propositions
- Competitive positioning
- Success stories
This information is useful for PMMs. It's not useful for reps in the middle of a deal.
Reps need plays for a different reason: to know what to do next when they're stuck.
A rep is in a deal. The prospect raises an objection the rep hasn't heard before. The deal stalls. The rep doesn't know how to move it forward.
In that moment, they need one thing: a script that tells them exactly what to say or do next.
The plays that work are the ones that provide that script. Everything else is noise.
I learned this by watching our most successful sales play—one I didn't build. A senior rep created it on his own after closing three deals in a new use case.
The entire play was one Google Doc with four sections:
Trigger: How to identify prospects who have this problem Opening message: The cold email that got responses Discovery questions: The five questions that surface urgency Objection responses: Scripts for the three objections every prospect raises
That's it. No market context. No buyer personas. No positioning strategy.
And reps used it constantly. Because it told them exactly what to do at each stage of the deal.
How to Build a Play That Gets Used
When I rebuilt our sales play process, I started with a different question. Not "What should reps know about this market?" but "Where do reps get stuck in these deals?"
I identified a new opportunity: selling to companies who just raised a Series A. These companies suddenly have budget and need to professionalize their operations. Perfect timing to buy our product.
Instead of researching and writing a play myself, I called three reps who'd recently closed Series A deals and asked:
"How did you find these opportunities?"
"What did you say in your first message that got a response?"
"What questions did you ask that revealed urgency?"
"What objections came up and how did you handle them?"
I took notes. Then I called three reps who'd lost Series A deals and asked the same questions.
The difference between the won deals and lost deals revealed exactly what the play needed to include.
Won deals: Reps targeted companies within 30 days of funding announcement. Lost deals: Reps waited 60+ days when the prospect was already talking to competitors.
Won deals: Reps opened with "Congrats on your funding. Most Series A companies we work with face [specific challenge]. Is that on your radar?" Lost deals: Reps sent generic "checking in" messages.
Won deals: Reps asked "What's the first thing your investors want to see improved?" to surface urgency. Lost deals: Reps asked about features and capabilities.
Won deals: Reps handled the "we're not ready yet" objection by saying "That's what everyone says right after funding. The companies that start now are the ones who have their systems in place when they start scaling." Lost deals: Reps accepted the objection at face value.
I didn't need to research or theorize. The reps who were already winning these deals had figured out what worked. I just needed to document it.
Building the Play With Reps, Not For Them
Here's what I did differently the second time:
Instead of writing the play myself, I scheduled a 90-minute working session with the five reps who'd closed Series A deals.
I put their winning patterns on a screen:
- Target companies within 30 days of funding
- Open with specific challenge
- Ask about investor expectations
- Handle "not ready" objection with peer proof
Then I said: "Let's turn this into a play you'd actually use. What else do you need?"
The conversation that followed created the play:
Rep 1: "I need a list of where to find funding announcements."
We added: "Monitor Crunchbase alerts, TechCrunch funding roundups, and LinkedIn 'congrats on the funding' posts."
Rep 2: "That opening message is good but I need three variations for different roles—CEO, VP Ops, Head of Revenue."
We wrote three message templates together on the call.
Rep 3: "The 'not ready' objection comes up every single time. I need more ammunition."
We workshopped three different responses based on what had worked in actual deals.
Rep 4: "What about when they say they're already looking at competitors?"
We added a section on competitive positioning specific to the post-funding context.
By the end of the session, we had a complete play. But more importantly, we had five reps who felt ownership of it because they'd built it together.
When I documented it and shared it with the team, those five reps evangelized it. "You should use this—it's working really well." That peer endorsement is worth more than any training I could run.
What the Play Actually Looked Like
The final Series A play was four pages. Here's the structure:
Who This Is For Companies that raised Series A funding in the last 30 days. Targeting CEO, VP Operations, or Head of Revenue.
Why They Buy Now Post-funding, companies need to professionalize operations to show investors progress. They have budget but limited time. They're overwhelmed with vendor pitches so you need to stand out.
How to Find Them
- Crunchbase funding alerts
- TechCrunch funding roundup (published Wednesdays)
- LinkedIn posts (search "congratulations" + "Series A")
- Your network's portfolio companies
Opening Message (3 Variations)
For CEO: "Congrats on your Series A! I work with a lot of post-funding companies and the #1 challenge they mention is [specific problem]. Is that on your radar as you scale? Worth a 15-min conversation?"
For VP Ops: "Saw you just raised a Series A—congrats. Most VP Ops we work with are getting pressure to professionalize [area] now that there's investor scrutiny. Sound familiar? Happy to share what's worked for others."
For Head of Revenue: "Congrats on the funding. Series A is usually when revenue leaders start feeling the pain of [specific problem]. Seeing that yet? I can share what [similar company] did."
Discovery Questions
- "What's the first thing your investors want to see improved?" (surfaces priorities)
- "What systems are you outgrowing fastest?" (reveals pain)
- "What's your timeline for getting [area] professionalized?" (tests urgency)
- "What happens if this isn't in place by [next fundraising milestone]?" (creates consequence)
Common Objections & Responses
"We're not ready yet—we just raised funding." "That's what every company says right after funding. But the companies that start now are the ones who have systems in place when they start scaling. [Customer X] waited 6 months and ended up in scramble mode. [Customer Y] started immediately and it was running smoothly by the time they needed it."
"We're already looking at competitors." "Smart—you should evaluate options. What's most important to you: fast implementation or comprehensive features? Most post-Series A companies prioritize speed because they need wins fast. That's where we differentiate."
"We don't have budget allocated for this." "You just raised $10M+ so budget usually isn't the blocker—it's prioritization. If this doesn't get prioritized in the next 90 days, what's the consequence? Will investors start asking questions you can't answer?"
Proof Points
- "[Company A] implemented in 3 weeks post-Series A and showed 30% improvement in [metric] by their next board meeting"
- "[Company B] switched from [competitor] after 6 months of slow implementation—we got them live in 4 weeks"
- "[Company C] used this to prove operational maturity during Series B fundraising"
Success Metrics Target: 40% response rate on outreach, 25% of responses convert to demo, 20% close rate.
That's the entire play. Notice what's not in it: no market sizing, no detailed buyer personas, no competitive battle cards. Just the scripts reps need at each stage.
How We Knew It Was Working
Two weeks after launching the play, I checked usage. Not by tracking document views—by listening to calls.
I pulled Gong recordings of reps talking to Series A companies. Were they using the opening messages? Were they asking the discovery questions? Were they handling objections with the scripted responses?
In the first two weeks, 8 reps used the play. Six of them got demos scheduled. That's 75% success rate.
More importantly, reps were adapting the play based on what worked. One rep modified the CEO opening message to mention a specific investor: "Saw Sequoia led your round—we work with a lot of their portfolio companies on [problem]."
That variation worked even better. I added it to the play.
Another rep found that asking "What's your investors' #1 concern right now?" got better responses than our original discovery question. I swapped it in.
The play became a living document. Reps used it, improved it, and shared what worked. That's when I knew it was succeeding.
The Plays That Don't Need Building
Here's what I learned after building 12 sales plays: most of them don't need to exist.
Reps only need plays for situations where they consistently get stuck. If reps are already winning deals in a segment without a formal play, don't build one. You'll just create documentation nobody needs.
Before building a play, I now ask:
Are reps struggling to close deals in this segment? If yes, a play might help. If they're already closing, leave it alone.
Is there a pattern to why they're losing? If reps lose for different reasons every time, a play won't help. If they lose for the same reason repeatedly, a play can address it.
Do reps ask for help with this? If reps are asking "How do I handle X objection in these deals?" that's a signal they need a play. If they're not asking, they don't.
I've stopped building plays proactively. I only build them when reps signal they're stuck and I see patterns in what's working versus what's not.
The Biggest Mistake PMMs Make With Sales Plays
The mistake I made—and still see PMMs make—is treating sales plays like strategic documents instead of tactical scripts.
We want to demonstrate our market intelligence. We want to show we understand the buyer. We want to prove we've done research.
So we build comprehensive documents with market analysis, buyer personas, and strategic positioning.
And reps ignore them because none of that helps in the moment when a prospect says "How do you compare to [competitor]?" or "We don't have budget right now."
The plays that work answer one question: "What do I say next?"
If your play doesn't answer that question clearly and quickly, reps won't use it.
Start With One Play
If you've never built a sales play before, start with one. Not five plays for five different segments—one play for one specific situation where reps are stuck.
Find the pattern:
- Pull three won deals and three lost deals in that situation
- Interview the reps: what worked in wins? what went wrong in losses?
- Document the pattern: how to identify these opps, what to say to get meetings, what questions reveal urgency, what objections to expect
Build it with reps in a working session. Don't write it in isolation and present it finished.
Test it with three reps for two weeks. See if they use it. See if it improves their results.
Iterate based on what works. Add successful variations. Remove what doesn't get used.
That's a sales play. Not a strategy document. Not a research project. A tactical script that helps reps know what to say when they're stuck.
Build that and reps will use it. Build anything else and it'll sit in a shared drive gathering dust.