TFT: Re-Engage with Timing, Not Nagging

Triggers, value touches, and referrals that spin the flywheel

Most “no’s” are “not now.” Timing wins what pressure can’t.

Your 90-day re-engagement rhythm keeps the flywheel turning and turns happy customers into repeat buyers and referral sources. New acquisition is 4–5× the cost of retention, so protect momentum with smart, value-first follow-ups.The right time to re-engage:

1. Know the moment (triggers)

2. Lead with value (not “just checking in”)

3. Earn referrals the right way

But first as always a small ask….

Do you know someone building something great? Do they need help re-engaging with their clients? Share this article so we can all grow a little bit.

If you have not subscribed….now is the time! Never miss another article and engage with a great community.

Knowing the Moment

You won the work and your have a satisfied customer….now what? Move on to the next? Yes. Ask for a review or testimonial? Sure. But when?

Timing is key to getting great answers and building trust with your customers. You want to make sure that their problem has been solved. You also want to ensure that you are staying ahead of future problems. There are a few moments that could drive your re-engagement, consider:

• Product launch

• Role change

• Hiring signals

• Fundraising

• Usage dips/spikes

• Renewal windows

These are also times when the customer will need to hear from you. But you want want to work on a cadence of 30, 60, or 90 day check-ins as well. These check ins are not driven by anything other then ensuring the problem you set out to solve is being solved. Consider open-ended questions like:

• Did we solve your problem?

• What value you have seen over the last 30/60/90 days?

• Would you recommend this product to others?

• What is the next problem you need to solve?

  • This one is key to keeping your product ahead of customer problems.

Finding time to re-engage with your customer ensures satisfaction. It also builds trust and loyalty.

Did You Solve the Problem

Outcomes build your revenue flywheel.

You were hired to solve a problem. Part of the reason for the follow-up (or re-engagement) is to ensure that problem was solved. Pretty simple and straight forward. As you engage with your customers you want to have two key steps in the process:

1. Naming their problem + micro-asset.

   1. This is going to be early in the process as you onboard them.

   2. Ensure agreement on the problem and assetment.

   3. Now we have a baseline to build from

2. 30/60/90 days later: relevant proof or checklist.

   1. This is validation of the work you have done.

   2. You want confirmation that you are indeed solving the customers problem.

Goal: confirm the outcome, surface the next one. Have we solved that problem? Or are we at least on the path to solving it? If “not now,” you’ve still added force without adding friction.

Turn Proof into Referrals

Now you know you have brought value to this customer and you want to build off of that. Testimonials are a great way to do that, but even better is a referral. Your current customer fresh on a problem solved going out and finding you new customers. You can consider programs like:

• “Founder’s Circle” perks/credits

• One-click referral flow

• Reward both sides

The key is you want to make it as simple as possible for your customers. Even a warm intro e-mail can be helpful. Remember they have a business to run too and it is not yours. Keep it simple for them.

Consider compositing a mini-case study for them to fill in:

Hand them a mini case to personalize:

“Since we last spoke, we [result]. If one person in your network would benefit, who comes to mind, and why?”

Action Step

Pick one trigger (e.g., usage spike/drop).

Build a 2-touch re-engagement and a one-click referral ask.

Send to 15 past leads.

Additional Readings

• Cold Calls… Why You Don’t Need Them

• From Funnels to Flywheels

• How to Attract New Customers Without Alienating Old Ones

• Seizing the Agentic AI Advantage

• The Impact of AI on Customer Success and Renewal Teams (TSIA)

Single-Page Checklist (Re-Engage)

• Choose primary trigger (funding/role change/launch/renewal)

• Draft 150-word value touch + 2-min Loom per ICP

• Schedule 2nd touch (7–10 days) with micro-proof

• Set up two-sided referral (“Founder’s Circle”)

• Track re-open, meetings, referrals, referral→SQO

• Are you looking to improve your sales process or hire your first sales professional?

• Are you a technical expert ready to transition into sales and need guidance?

If so, we’re here to help! Reach out to us with your specific challenges, and we’ll schedule a time to discuss how we can develop a customized plan to meet your goals.

Who else needs to learn this? Share this with one friend today. Thanks for your time and for Sharing!