Winning the Game, 3 Ways to Beat The Competition by Nick Butler

“On the kickoff call with Acme, when we asked ‘Why did you select Jiminny?’ The answer was clear - Nick has provided a high level of service. He’s been very responsive throughout their selection process, answering all questions and overall setting the standard high for what customers can expect of Jiminny. They felt, when in direct comparison with Gong, that with Jiminny they were ‘in good hands.’”

- Customer Success Director, Jiminny

That feedback stuck with me. Not because it was flattering, but because it reinforced something I deeply believe: how you run a trial is often the reason you win or lose the deal.

The majority of sales cycles involve some sort of trial or proof of concept (PoC).

In theory, this should be the moment of truth where your product shines. In reality? This is where most reps take a step back and begin to lose the deal before the trial has even begun.

They assume the heavy lifting is done. They hand it off to CS. They send a follow-up email, maybe schedule a wrap-up call, and hope for the best.

Meanwhile, their competitor is embedding themselves in the customer’s Slack channel, running enablement, and showing up in every meeting like a product expert who knows their business.

Guess who’s winning that deal?

At Jiminny, we sell to revenue teams, some of the most skeptical and sophisticated buyers on the planet. Our tech helps them improve conversations and drive outcomes, so if I don’t nail the trial, I am the case study for what not to do.

Here are three things I do in every trial to beat the competition and stay in control, beyond the obvious stuff like setting clear next steps and defining decision criteria (I’m assuming you know that already!)

1. Become a product expert and stop outsourcing your value

You can’t add value in a trial if you don’t deeply understand your product.

I made a decision early on to become a master of the platform. Not just to know the high-level benefits, but to be able to troubleshoot configs, answer in-depth questions, and lead product demos without calling in backup.

It changes the conversation. Customers see you not just as a seller, but as a guide. You’re no longer a middleman, you’re someone who understands the problem and the solution.

Don’t get me wrong, I still work closely with our Solutions team. But when I show up with answers instead of questions, they’re a force multiplier, not a crutch.

2. Own the trial, do not shirk responsibility

Too many AEs treat a trial like a baton handoff: “Here you go, CS! Let me know how it turns out.”

I don’t let go of the wheel.

I’m involved in every part of the trial journey. That includes:

Technical setup - working directly with IT or Rev Ops to ensure a clean launch

Enablement sessions - often running these myself, tailored to different user groups

Mid-trial check-ins - surfacing usage insights, re-aligning on goals, removing blockers

This means I stay ahead of objections, confusion, or disengagement, because I’m in the room when those things bubble up.

3. Make communication frictionless

One of the biggest trial killers? Slow, fragmented communication.

A quick question turns into a 3-day email thread. Users get stuck and stay stuck. Internal champions can’t move fast enough to get support.

To avoid that, I always ask if we can spin up a shared Slack or MS Teams channel.

Now, they can ping me directly, or loop in a new stakeholder and we get to resolution in minutes, not days.

Final Thought: Trials Don’t Win Themselves

A trial is not a free pass to close. It’s a high-stakes audition and your competitors are working just as hard to land the role.

By owning the process, embedding yourself in the customer’s world, and showing up like a partner (not just a rep), you earn trust and the deal.