Yesterday I was talking to a founder who runs a medical transportation company. They provide vans, drivers, and logistics for nursing homes and hospitals.
Here’s his problem: the sales cycle is a beast. You spend months wooing a prospect, working the RFPs, sitting through endless meetings — and if they finally come back and say “no,” you’re screwed. All that time, all that energy… gone.
So he asked me: “Should we create a smaller product, so when they say no to the full package, we don’t lose the relationship altogether? or is it just a distraction?”
I love that question because it’s not just about his business. It’s a problem that haunts anyone selling big-ticket products with long sales cycles.
Enterprise SaaS. B2B services. Healthcare, finance, logistics.
If the deal’s all-or-nothing, you’re playing Russian roulette with your pipeline.
That’s why I coach founders on building what I call the 3R Framework for Downsells: Reframe, Reduce, Recover.
Here’s the framework I gave him:
Reframe: Position the Offer to Lower the Barrier
The first step is shifting how the customer sees your product.
Big contracts feel like big risks; politically, financially, emotionally.
The job is to lower the barrier.
For example, take KISSmetrics. Early on, prospects thought it meant ripping out Google Analytics. That was terrifying. So they reframed it: KISSmetrics works alongside GA. It’s a side-car, a ride-or-die.
Conversion rates jumped once buyers realized it wasn’t an all-or-nothing switch.
Same principle applies here. My founder’s big promise was: “We’ll handle your entire transportation program.” But what his customers really feared was getting dinged on a Medicare score b/c one of their patients missed a single dialysis appointment.
That’s the pain point.
If he reframes around that — “we’ll make sure your critical patients never miss a ride” — suddenly the ask feels smaller, safer, and easier to buy.
You can even reframe your trial. Call it a “paid pilot” instead of a proof-of-concept. The wording alone signals commitment and makes it easier for the buyer to sell internally.
Reduce: Strip Away Scope, Not Value
Once you’ve reframed the problem, cut the scope without cutting the value.
Ways to reduce:
Volume: Instead of 100 rides a week, offer 10 for emergencies.
Time: Run a 90-day pilot instead of demanding a 3-year contract.
Scope: Handle compliance and dispatch, let them keep their drivers.
Risk: Offer overflow capacity they only pay for if used.
This is exactly what many SaaS companies do with tiered products or pilots.
Jason Lemkin says “bet on yourself and deliver the service the way the customer is most comfortable with.”
Big companies often expect new vendors to prove themselves, so don’t think of a smaller deal as a step down — it may just be the only way in.
For my founder, we landed on an “overflow” package. Elderly care facilities wouldn’t need to overhaul everything. They’d just call him when flu season spiked or a snowstorm hit and they didn’t have drivers to cover the volume.
Lower commitment, high relevance.
Recover: Salvage the “No”
Even if the big deal falls apart, a downsell lets you salvage the relationship.
Here’s what happens when you don’t: Gartner shows uncertain buyers are 30% less likely to sign any deal, and 40% less likely to sign a big one.
That’s a lot of lost pipeline just because there’s no middle option.
Here’s what happens when you do offer one:
You keep a light contract that keeps your logo on their books.
You create a case study that makes the next buyer less scared.
You build trust inside the org, which makes upsell conversations easier.
I’ve seen this play out over and over.
A startup pitches a massive solution, gets rejected, then comes back with a smaller pilot.
Months later, that “pilot” crushes and evolves into a full contract because the value was proven.
For my founder, that might mean a hospital says “no” to full outsourcing but “yes” to a standby contract for overflow rides.
Not glamorous. Not huge. But it keeps the door open, and that’s the point.
The Bigger Point
The danger is inventing a cheap, distracting product that takes you off mission.
The opportunity is designing a downsell that’s an entry ramp.
It makes the first sale easier.
It proves your value faster.
It keeps you in the room when bigger budgets show up.
That’s how you survive long sales cycles without bleeding out.
Reframe. Reduce. Recover.
Don’t always think about things in the most binary way (“win or lose”), instead it could just be about getting your foot in the door or nothing at all.
If you liked this blog post, you might enjoy this other one on the 5 founder questions I answered this past week.
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