You probably do treat most of your oldest, longest lived customers far worse than a new prospect. As crazy as that sounds at some level.
We’ve talked enough about our really, really rough experience with old, dated Adobe Marketo for marketing automation. They broke our unsubscribe link for weeks. Then they blamed us. Then they blamed Beehiiv (which we don’t use). Then they blamed Salesforce. Then they forced us into multiple calls with no resolution.
About as bad an experience as you can get out of a B2B vendor.
So bad, we just vibe coded our own unsubscribe experience in Replit in an afternoon. Built and shipped a replacement for a core feature of a $60K+/year product, because the vendor couldn’t or wouldn’t fix their own CAN-SPAM violation.
But honestly? It’s worse than that.
I Was One of Marketo’s First 10 Customers. In 2006.
The founders sold me personally. In our office. I was one of their very first ten paying customers, before anyone had heard of them.
Since then, we’ve used Marketo across 3 different legal entities. We took a break for a few years when Mailchimp was all we needed. Then we came back. All-in-all, a 20-year customer relationship.
And what did 20 years of loyalty get us in 2026?
Years of price increases. And zero help when we actually needed it.
Just blame. Blame the integration. Blame Salesforce. Blame Beehiiv (again, we don’t use it). Blame “something you’re doing.” Never a fix. Never an ETA. Never a ticket owner. Never a “we’ll get back to you Friday.”
For a CAN-SPAM violation on the most basic feature an email marketing platform has.
Marketo Isn’t Unique
They’re just the most extreme example of a pattern running through almost every pre-AI era B2B company right now:
We bend over backwards to get new customers. We onboard them with white glove care. We spin up Forward Deployed Engineers. We send the CEO into the sales cycle. We do custom integrations on the house. We give the new logo whatever they need to close.
And then we abandon them.
We move the customer success rep to a new account. We auto-renew the contract. We push 8-10% price increases every cycle. We ship them new “AI bundles” they didn’t ask for. We make support harder to reach. We tell them to file a ticket.
And when something actually breaks, like a CAN-SPAM violation? We blame their integrations.
The 20-Year Tax
A new customer at SaaStr gets pitched, demoed, courted, and onboarded with care. Maybe a steak dinner. Definitely a Slack channel.
A 20-year customer at SaaStr AI gets a renewal email, a price increase, and a support queue. The CSM rotates every 14 months. Nobody who originally sold us is still at the company. Nobody remembers we were a case study. Nobody remembers we sent them dozens of referral logos. Nobody remembers anything.
That’s the 20-year tax. The longer you stay, the worse you get treated. Because new customers have leverage. They haven’t signed yet. Old customers have already signed, already integrated, already trained their team, already wired the data flows. So they get squeezed.
For a long time this worked. Switching costs were high. Building the alternative yourself was impossible. So vendors got away with it.
That math has flipped.
The Switching Cost Equation Is Collapsing
When Claude is this good, and Replit (or Cursor, or Lovable, or whatever you use) can ship production code in an afternoon, the switching cost side of the equation collapses entirely.
Customers don’t even need to find a new vendor. They can just build the specific thing the incumbent is failing at.
A team of 3 humans plus some AI agents shipped a working unsubscribe handler in a few hours. Five years ago that story doesn’t happen. You’d wait in the Marketo queue. You’d pay an agency $300/hour to maybe build a workaround over a few weeks. The workaround is trivial now. Claude plus Replit plus an afternoon.
Multiply that across every legacy B2B product. Every annoying limitation. Every dated UX. Every API that hasn’t shipped a meaningful update since 2019. Customers can patch around all of it now. And every patch they ship is one more reason they don’t need to renew.
What This Means for Founders
If you’re running a B2B company at any scale:
- Do your 5+ year customers get the same treatment as your new logos? Not a renewal email. Actual treatment. Does anyone on your team know who they are, what they bought, why they stayed, who their champion is, and what they need next?
- Does your support queue treat ARR equally? Or do new accounts get fast lanes while loyal customers wait three days for someone to blame their integrations?
- Does your pricing reflect the relationship? A 20-year customer paying more than a brand-new logo for the same product is a sign you’ve stopped competing for them and started taxing them.
- Are price increases doing the work that net new logos used to do? This is the Chief Price Raising Officer trap. When growth slows, the path of least resistance is squeezing the base. It works for 2 to 4 quarters. Then you wake up and realize your best long-term customers are quietly building replacements.
- When something breaks, who owns it? A 20-year customer should not have to escalate to engineering, get on three calls, and be told “it must be something you’re doing.” That’s not a support process. That’s a churn engine.
The Real Problem Is Organizational
The reason Marketo can’t fix the unsubscribe link isn’t really technical. It’s organizational. The product team isn’t investing in the platform. Support is a cost center being shrunk. Engineering is allocated to AI features for the new logo deck. Nobody is incentivized to care about a 20-year customer’s broken core feature, because that customer’s renewal is just a number in a forecast.
The new logo, on the other hand? That gets a war room.
The gap between how you treat a new logo and how you treat a 10-year customer has gotten so wide that the 10-year customers are noticing. And they have the tools to do something about it now.
Flip it. Treat your 20-year customer like a brand-new $1M ACV deal. Pick up the phone when their unsubscribe link breaks. Send the CTO. Send the founder. Fix it in 24 hours and apologize.
Because if you don’t, they’re not going to file a churn risk ticket. They’re just going to vibe code the fix themselves. And then they’re going to write the post.
Treat the Loyal Like the New. In Fact, Treat Them Life Their Total Lifetime Value.
The best customers you have are the ones who’ve been with you for 5, 10, 20 years. They’ve referred you logos. They’ve spec’d your features. They’ve defended you in the Slack channels you don’t see.
You owe them more than a price increase and a support queue. You owe them at least the level of care you give a stranger you’re trying to close.
Otherwise, they’ll just build the fix themselves. We did.
