Latest / Closing the Deal with Fexingo: Sales, Negotiation, and Revenue Conversations for Operators / The Sales Rep Who Won by Asking to Be Second-Choiced
Transcript
- Lucas: So there's a sales rep I've been following — let's call her Sarah. She's at a mid-market SaaS company, selling a project management tool into financial services. And she's up against a deal that should be dead. Luna: Dead how? No budget, no urgency, or she just got outmaneuvered? Lucas: Worse. The prospect — a mid-sized hedge fund — had already picked a vendor. They were in final contract review with a bigger, more established competitor. Sarah's company wasn't even formally rejected; they were just... ignored. The evaluation cycle had moved on without her. Luna: So she's late to the party and the party's basically over. What does she do? Lucas: She asks for something almost nobody asks for: she asks to be the second choice. Luna: Second choice? Like, 'Hey, if your first pick falls through, call me'? That's not a close — that's a consolation prize. Lucas: Right, but she didn't frame it as a consolation. She said something like, 'I know you're leaning toward Vendor X. I respect that. But if for any reason that deal doesn't close — price, implementation, legal — I'd like you to have a fully baked alternative ready to go. Let me be your fallback, and I'll make sure you're not starting from scratch.' Luna: And the buyer said yes to that? Lucas: Surprisingly often, yes. Because it's low risk for the buyer. They're not committing to anything. And Sarah positioned it as a service to them — protecting them from a disruption if the primary deal falls apart. Luna: Okay, so she gets a second meeting. But then what? She's still the underdog. Lucas: That's where the real strategy kicked in. She didn't just sit back and wait. She asked for a detailed walkthrough of what the incumbent proposed — scope, pricing, implementation timeline. And she mapped every single gap. Not just features, but things like onboarding support, data migration, compliance certifications. Luna: And she found gaps? Lucas: Several. The incumbent's implementation timeline was 12 weeks. Sarah's company could do it in 6. The incumbent had a separate charge for data migration; Sarah bundled it. And the incumbent's compliance docs were still pending a SOC 2 renewal; Sarah's were current. Small things individually, but together they made a compelling case. Luna: But the buyer had already chosen — weren't they biased to overlook those gaps? Lucas: Some were. But here's the key: the buyer's internal champion for the incumbent had to go to their boss and justify the choice. And the boss, being a fiduciary, asked, 'Are we sure this is the best fit?' That opened the door for Sarah to present her comparison document — not as a sales pitch, but as a 'here's what you should know if you go with the fallback.' Luna: So she's leveraging the fact that the buyer's own procurement process demands a justification. Smart. Lucas: Exactly. And then — this is the part I love — the incumbent's deal hit a snag. Their legal team couldn't agree on a data-processing addendum. The deal stalled. And suddenly the buyer's team is looking at Sarah's fully baked alternative, which is ready to go. Luna: So the second choice becomes the first choice by default? Lucas: Not by default — by preparation. Sarah had already done the work: she had a signed NDA, a draft contract, a proposed timeline, and references ready. When the incumbent stumbled, she could close in two weeks. The buyer later told her, 'If we had to start over with another vendor, we'd have lost a quarter.' Luna: There's a lesson there about being ready for opportunities that don't look like opportunities. Lucas: And about asking for a position that feels weaker but actually gives you a structured pathway into the deal. You're not fighting to be first; you're fighting to be the only viable alternative. Luna: I want to pause on that, because it's counterintuitive. Most reps would say, 'If I'm not the first choice, I'm out.' Sarah said, 'If I can't be first, let me be second.' And she turned second into a win. Lucas: Yeah. And it's not just about being patient. It's about creating a contingency plan for the buyer that they didn't know they needed. You're reducing their risk. And in enterprise sales, risk reduction often beats feature advantage. Luna: Let's talk about the numbers. What was the deal size? Lucas: About $450,000 annual recurring revenue, with a three-year contract. So north of $1.3 million total contract value. Not life-changing for a big firm, but for Sarah's company — which was doing about $15 million ARR at the time — it was a significant win. Luna: And how did her manager react? I can imagine some sales leaders saying, 'Why are you wasting time on a lost deal?' Lucas: Her manager was skeptical at first. But Sarah framed the second-choice play as a low-cost experiment. She said, 'Give me two weeks and one more meeting. If it doesn't move, I'll drop it.' The manager agreed because the opportunity cost was low — she wasn't neglecting other deals. She was reprioritizing a dead pipeline entry. Luna: So there's a time-boxing element too. She didn't chase it indefinitely. Lucas: Right. She set a specific checkpoint. After the first meeting as second choice, she'd evaluate whether the buyer was genuinely open or just being polite. If it was politeness, she'd walk. But she got signals — the buyer asked detailed questions, introduced her to the legal team, shared the incumbent's proposal — that told her there was real interest. Luna: What about the incumbent? Did they ever catch wind of what was happening? Lucas: Probably. But by the time they realized Sarah was a threat, the legal snag had already stalled their deal. And the buyer's team had already built a relationship with Sarah. The incumbent tried to match her pricing and timeline, but they couldn't compress their implementation — it was a product limitation, not a negotiation point. Luna: So the second-choice strategy works best when you have a genuine operational advantage, not just a cheaper price. Lucas: Absolutely. If the only difference is price, the incumbent can usually match or at least narrow the gap. But if you have a structural advantage — faster deployment, better compliance, stronger support — you can differentiate even as the second pick. Luna: I'm thinking about the psychology on the buyer side. When someone asks to be second choice, it signals confidence. It says, 'I know I'm good enough that if the first option fails, I'm the obvious next call.' That's a powerful subtext. Lucas: It also signals humility. The rep isn't demanding to be first. They're acknowledging the buyer's process. And buyers appreciate that — especially when they're dealing with pushy salespeople. Sarah told me that several buyers said, 'You're the only rep who ever asked to be second. Everyone else either gives up or gets aggressive.' Luna: That's a differentiator in itself. So what's the takeaway for reps listening? How do you actually execute this? Step one: identify a deal where you're clearly not the frontrunner but still have a relationship. Lucas: Step two: ask for the second-choice role explicitly. Use language like, 'I'd love to be your contingency plan. If anything changes, you'll have a ready alternative.' Step three: do the work to make that contingency real — draft a contract, prepare implementation docs, get legal pre-approved internally. Luna: And step four: don't wait passively. Stay engaged. Check in periodically without being annoying. Send relevant content. The goal is to be top of mind when — not if — the primary deal hits a bump. Lucas: Exactly. And one more thing: this tactic works best in deals with multiple stakeholders. If there's only one decision-maker, the second-choice play is harder because there's less internal friction to exploit. But in complex B2B sales with procurement, legal, and end-users, there's almost always a point where the incumbent stumbles. Luna: Sarah's story is a good reminder that 'no' doesn't always mean no. Sometimes it means 'not right now' or 'I've already chosen, but I'm open to being wrong.' Lucas: And that's the core of it. The second-choice ask reframes rejection as a deferred decision. It keeps the door open without forcing the buyer to reverse their initial choice. That's a subtle but powerful shift. Luna: If today was actually useful to you, the way these stay ad-free is listener support — buy me a coffee dot com slash fexingo. Lucas: Yeah, that's right. A small gesture goes a long way in keeping the conversation going. Luna: So back to Sarah — she closed the deal in the end. But I'm curious: did she ever use the second-choice tactic again? Lucas: She did. She told me she's used it three more times since, and two of those turned into wins. The one that didn't work was a deal where the incumbent's contract was already signed — no contingency clause, no out. But in the two that closed, the pattern was the same: the incumbent hit a roadblock, and Sarah was ready. Luna: So the success rate isn't 100 percent, but the cost of trying is almost zero. That's a bet worth taking. Lucas: Right. And it changes the way you think about pipeline management. Instead of writing off deals where you're not the frontrunner, you categorize them as 'active second-choice opportunities.' That gives you a structured way to nurture them without wasting energy. Luna: I like that reframing. It turns a loss into a strategic position. Next time I'm in a competitive deal, I'm going to remember Sarah's approach. Lucas: Same here. The second-choice play is one of those counterintuitive tactics that only works if you're confident enough to ask for less — and then deliver more. Luna: Alright, that's a wrap for this episode. Thanks for listening. Lucas: And if you have a story about a deal you won from a losing position, we'd love to hear it. Reach out to us at Fexingo.