Latest / Closing the Deal with Fexingo: Sales, Negotiation, and Revenue Conversations for Operators / How One Sales Rep Won by Asking for a Pilot Program
Transcript
- Lucas: Let me tell you about a rep named Jenna who sold enterprise CRM software. She had a target account — 400 employees, about 90 sales reps, three different CRMs already in use. The VP of Sales was skeptical of yet another platform. Jenna didn't push for a full rollout. Luna: So what did she do? She asked for something smaller? Lucas: Exactly. She asked for a 30-day pilot with exactly one team — the VP's own team of eight people. No contract, no upfront payment, just a test. If it didn't work, she'd walk away. The VP agreed, mainly because the ask was so low-risk. Luna: But wasn't Jenna taking a huge risk? Eight reps might not love the software, and then she's out. Lucas: She was confident in the product, sure, but more importantly, she understood the psychology. By making the entry step tiny, she got the VP to start the relationship. Once the team used it and saw results — 15 percent more leads logged in the first week — switching costs set in. The VP's own reps started asking why the whole company wasn't on it. Luna: Classic foot-in-the-door. First a small yes, then a bigger one. Lucas: Exactly. Jenna also made sure the pilot had a clear success metric. She worked with the team lead to define what 'good' looked like — number of leads tracked, time saved per rep. That made it easy to justify expanding after the 30 days. Luna: But what if the pilot had failed? Doesn't that sometimes just give the buyer a free trial and they walk away? Lucas: Sure, that happens. But Jenna only pursued a pilot when she knew the product would outperform. She pre-qualified the buyer — if their process was too messy or they lacked executive support, she wouldn't offer a pilot. It's not a tactic for every deal. Luna: So it's about reducing risk for the buyer, not giving away free value. Lucas: Exactly. And the interesting thing is, after the pilot, the VP didn't just buy for his team. He championed the expansion internally. Jenna had turned a skeptical buyer into an internal advocate — all because she asked for the smallest possible yes first. Luna: It reminds me of the classic 'yes ladder' in negotiation. Start so low that 'no' feels awkward. Lucas: Right. And psychologically, once the buyer commits to the pilot, they start to justify their own decision. They root for the pilot to succeed because it validates their choice. Jenna didn't have to sell them later — they sold themselves. Luna: That's powerful. And if you've ever negotiated a deal where a pilot saved the day, you know how valuable this approach can be. Lucas: Honestly, if today's episode was worth a coffee to you, you can find us at buymeacoffee dot com slash fexingo. That link keeps the show ad-free and independent. Luna: Yeah, listener support really does help us keep episodes like this coming. So thanks for thinking of us. Lucas: Back to Jenna. After the pilot, she didn't just ask for the full company rollout. She first asked the VP to present the pilot results to the other sales directors. That created peer pressure and data-driven buy-in. Luna: So she used the pilot evidence to let others sell for her. Lucas: Exactly. The VP showed a 20 percent increase in pipeline coverage during the pilot. The other directors wanted in. Jenna closed a seven-figure deal within two quarters — and the pilot cost her almost nothing. Luna: What about the risk of a pilot dragging on? Some buyers will just keep extending the trial. Lucas: She built a timeline upfront. Day 21, they'd review results. Day 30, the pilot ends unless there's a signed agreement to expand. No extensions. That urgency prevents stagnation. Luna: So the key is to structure the pilot with a clear end date and escalation path. Lucas: Exactly. Jenna's story shows that asking for less can get you more. The smallest possible commitment is often the gateway to the biggest deals. Luna: And it requires reps to be confident enough in their product to let it speak for itself. Lucas: That's the bottom line. Next time you're stuck in a negotiation where the buyer hesitates, think about what the smallest 'yes' could look like. It might just be a pilot.