The Question Nobody Asks
Want to displace an incumbent vendor? Stop pitching and ask: "What would it take for you to move over to us? What problem could we completely solve for you, so you would switch?"
Most reps send competitive battlecards. Most CROs lean on G2 grids. None of that addresses why a customer would rip out a system their team already uses.
Switching costs more than the pricing conversation reveals: migration, retraining, re-integrating, buying out the remaining term, and the political risk to whoever championed the incumbent. Being 20% better does not clear that bar. Customers move when something is actively broken and their current vendor will not fix it.
Why Direct Questions Work
Ask a specific question with no pitch attached and you usually get a specific answer within a day. People like talking about problems their current vendor ignores. An email that does not ask for a meeting is the easiest reply they will send that week.
You get one of four answers:
1. Something you already do well. The gap is now one demo and a migration plan. Most reps never find out they were already the answer.
2. Something on your roadmap. You have a design partner with a logo and a ship date. That is roadmap input with revenue attached.
3. Something you will never build. Walk away. You just saved two quarters chasing an account that was never going to close.
4. Nothing, or "a lower price." No real pain. They are using your quote to negotiate 15% off from the incumbent.
Three of those make you money. The fourth saves you a year.
The Email
Do not overthink it:
Subject: One question
Hi [Name],
You are on [Competitor] and if it is all running perfectly just ignore this.
But if not, what are the top issues? The top gaps we can fill at [Us]. We have gotten hundreds of customers to move over by solving problems like [X, Y and Z].
What is the one problem we would have to solve 100% to make it worth switching?
If we can, we will do it for you.
No calendar link. No deck. You are asking for a reply, which is far smaller than asking for a meeting.
Close the Switch
Getting the answer is half of it. Five things separate teams that close switchers from teams that just collect intel:
1. Go hyper-tailored. Come back with three to four specific ways you solve their problem, for their business, in their workflow. If they have to figure out what is better, you lost.
2. Offer to do all the work. The migration, implementation, integrations, data mapping, onboarding. Every one of those is a reason to say "not this quarter." Take them off the table explicitly.
3. Build collateral for the switch. A page that makes it obvious why changing is worth it. The bar for a switch is far higher than the bar for a first purchase.
4. Do buy-out deals. If they are nine months into a two-year contract, give them fifteen months free and sign them for a year after that. Zoom did this constantly against WebEx.
5. Get executive sponsorship. A founder-to-VP email gets read at a rate no SDR sequence will hit and gets a more honest answer, because they know you can actually do something about what they say.
Pick twenty accounts sitting on a competitor. Send twenty versions of that email. Do it once a quarter. That is an afternoon of work and it will teach you more about your competitive position than any analyst report.
Jason Lemkin is the founder of SaaStr and former CEO of EchoSign, acquired by Adobe. SaaStr Fund has backed companies including Salesloft, Pipedrive, and Talkdesk.