The Journey: #30 Renewals by Design

Let’s get one thing straight: Renewals don’t just happen.

They’re not a due date. Not a Salesforce stage. Not a task on your CSM’s to-do list.

They are the culmination of everything that came before. And yet, most companies treat them like a standalone motion instead of the result of strategic orchestration.

I’ve seen this mistake play out too many times. Reactive. Rushed. Riddled with guesswork.

Having run renewals at 5 different companies, I’ve seen them done really well and really poorly.

The Renewal That Almost Wasn't

At one company, the Account Management team owned renewals. Intentions were solid—but the process? Not so much. No centralized tracking. No accountability. Just a lot of assumptions.

One day, about three weeks from a critical six-figure renewal with a marquee logo, I realized I hadn’t seen an update. So I asked the AM about it.

Their response? “Oh, I forgot to follow up. I’ll do that now.”

WHAT?!

This wasn’t a renewal that was just going to roll in. We needed buy-in, likely some negotiation, and a tight execution plan. Because of the lack of process, tracking, and ownership, the deal slipped by nearly 60 days.

We eventually closed it, but it was way too close for comfort.

That was the moment I knew: Renewals must be designed, not assumed.

What Good Renewal Design Looks Like

Every company’s renewal motion is different but the best ones follow the same four principles:

1. Backplan from the Renewal

Don’t start with “When is it due?” Start with:

• When should we begin the conversation?

• What proof points do we need?

• Who needs to be involved?

Reverse-engineer from success → decision → signature

2. Segment the Strategy

One-size-fits-all doesn’t work.

• Low ARR / Low Complexity: Automated email, 90-day reminder, online quote.

• Mid-Market: CSM-led convo, health + ROI review, start 120 days out.

• Enterprise: Multi-threaded strategy, exec alignment, procurement—start 6+ months out.

Each segment needs its own timeline, team, and playbook.

3. Build Triggers, Not Tasks

Tasks get skipped. Triggers create action.

Examples:

• 180 days out → kickoff renewal prep

• Drop in usage 90 days out → trigger risk alert

• New stakeholder appears → exec sponsor play initiates

4. Decouple Renewal from Relationship

The renewal conversation should never be the first time you talk about value.

It should be the final confirmation that value has been delivered.

If you’re saving your best data for a QBR or renewal call, you’re already behind.

Smart Renewal Design is Proactive, Predictable, and Personalized

Stop asking: “Who owns the renewal?”

Start asking: “What system ensures nothing falls through the cracks?”

What you can do this week:

1. Map your renewal journey backward

2. Define separate processes for Enterprise vs SMB

3. Audit your CRM for missing renewal triggers

4. Document what “ready for renewal” really looks like

Don’t Leave Renewals to Luck

If your renewal motion feels chaotic, last-minute, or inconsistent, it’s not because your team isn’t trying. It’s because the process wasn’t built to scale, adapt, and win.

The truth is: You don’t need a miracle to retain your customers. You need a plan. Design it. Test it. Own it.

Because in Customer Success, retention isn’t a goal, it’s an outcome of great design.