I grew up in Ireland, where the kind of aggressive, hard-close selling that American sales culture tends to celebrate would feel almost rude. In the U.S., selling is part of everyday life. Everyone has been sold to, most people have sold something at some point, and the expectation that a salesperson will push for a decision is baked into how commerce works.
In parts of Europe, particularly where I’m from, cold calling and pushing for the close can feel almost taboo. So when I entered SaaS and cybersecurity sales, I leaned hard into what felt natural: building relationships.
I would build incredible rapport with prospects. I’d know their kids’ names, understand their business inside and out, and be on weekly calls during extended POCs, sometimes back-to-back, and half the time those calls weren’t even about the solution.
The problem was that when it came time to ask for the business, I felt like I was disrupting something I’d carefully built. I had become so entrenched in the relationship that introducing a closing moment felt transactional.
So instead of fixing the real issue, I created a workaround.
The Good Cop/Bad Cop Phase
Early in my career, when it was time to move a deal forward, I would make myself unavailable—a trade show, a travel conflict, a vague scheduling issue. My team lead would then step in to do what I wouldn’t: push for a decision. We fell into a good cop/bad cop dynamic that, while effective, was a workaround for my discomfort with the closing conversation.
It worked. Deals closed. Revenue came in. And I felt genuinely uncomfortable about it, because it revealed something about my own process that I hadn’t fixed.
I had built exceptional relationships with these prospects. I knew their businesses, their teams, and their pressures, but I checked out when it came time to ask for a commitment. As a sales leader, this was a problem I couldn’t ignore.
The good cop/bad cop approach was a symptom of a deeper issue: I had mentally separated the close from the rest of the relationship. By treating it as a distinct, high-stakes moment rather than a natural next step, the close felt transactional even when the relationship wasn’t. Fixing this required rethinking the entire arc of the sales conversation.
The Real Shift: Starting the Close Earlier
The breakthrough didn’t come from learning a better closing line or a new objection-handling framework. It came from realizing that the close isn’t a conversation you have at the end of the sales cycle. It’s a thread you weave throughout.
Once genuine value is established and the prospect understands what changes for their business if they move forward, the conversation about budget, packaging, and commitment is a natural extension of that value discussion, not a jarring pivot into commercial territory.
Once we’ve aligned on need and outcome, I move toward something practical and collaborative with questions like:
- Do you see this fitting into a core package, or are you thinking about a more comprehensive build-out?
- How many clients would you put on this in the first 90 days?
- How does that forecast as you grow your base over the next year?
These questions normalize budget discussions, frame commitment as collaborative, and surface misalignment on scope and investment before it becomes a last-minute objection.
When a quote causes the energy in the room to shift, it’s almost always because the budget was never anchored to value early in the process. The prospect was excited about the solution, but received a number that felt disconnected from the conversation.
This isn’t an objection problem. It’s a sequencing problem. The only way to make uncomfortable conversations comfortable is to have them early and openly.
Why the MSP Channel Demands This Approach
In enterprise SaaS, you can sometimes get away with more transactional pressure. Budget cycles, procurement timelines, and competitive dynamics can create genuine urgency that a well-timed push can capitalize on. The MSP channel doesn’t work that way.
MSPs talk to each other constantly. If you force a deal that wasn’t ready, and a customer goes live feeling pushed into something before they were operationally prepared for it, that story travels through the peer groups, the Slack channels, and the conference hallways where your next 20 prospects are already forming opinions about you.
That’s why the philosophy from my last post, “it’s not if, it’s when,” is more than a patience strategy. It’s a reputation strategy. When you tell a prospect who isn’t quite ready, “I appreciate where you are in your journey. Let’s stay close and revisit when the timing makes sense,” and then you follow through on that, something happens. The prospect doesn’t forget.
When they’re ready, when the budget aligns, and internal priorities shift, they call you first. Not because you had the best deck, but because you were the person who respected where they were instead of trying to drag them somewhere they weren’t.
Closing in this channel is about creating clarity together, not extracting a commitment. When the buyer feels like they’re making a decision with you rather than being talked into a decision by you, the close is clean, the onboarding is smoother, and the retention is better. All of that compounds over time.
What Closing Should Actually Feel Like
When you’ve built the relationship, sequenced the conversation correctly, anchored budget expectations to value early, and aligned on packaging and scope as part of the process, the final step isn’t dramatic. The buyer has been part of building the decision throughout. They’re not being asked to commit to something new. They’re being asked to formalize something they’ve already been working toward together.
The moment I knew my process had genuinely shifted was when prospects started ending calls with “Alright, what’s next?” They weren’t waiting to be asked. They’d already decided. No good cop needed. No bad cop needed. No manufacturing urgency from a trade show I suddenly needed to attend.
Just a process that had been pointing clearly in one direction from the beginning, built on a relationship that made the decision feel obvious rather than forced. That’s teachable and scalable. And in a channel built on reputation, it’s the only kind of closing that actually holds.
But even with the right hire, the right relationships, and a clean closing process in place, there’s one more piece that determines whether all of it produces predictable results. That’s what we’ll dig into next blog. Stay tuned!
If you want to build the scaffolding for the kind of process I’ve described here, the GTM Academy Sales Kit includes pipeline qualification tools, objection-handling resources, and sales process frameworks designed for cybersecurity sales. It gives your whole team a shared foundation to work from.
To your growth and success,
Shane