How to Automate Failed Payment Recovery

CATEGORY:

Sales

Offering flexible payment plans is a smart move for online coaches and service providers. They make your offers more accessible, give clients financial ease, and create consistent cash flow for your business.

In case you need a refresher, multi-payment plans are a win-win:

  • Lower the barrier to entry without lowering the value
  • Let clients pay in smaller, digestible increments
  • Create consistent monthly cash flow
  • Align with values like accessibility and inclusivity
  • Often boost your overall revenue compared to pay-in-full only

But (there’s always a but, right?) — failed payments.

Cue the awkward tension, like realizing you’ve been ‘on camera’ during that Zoom masterclass — bumbling around, eating your lunch, and fixing your messy bun for the class to enjoy.

The Hidden Tax of Payment Plans: Chasing Down Invoices

When a client’s card declines, it feels like a fun mix of awkward and frustrating. Do you:

A) Pretend it didn’t happen and hope they notice? B) Overthink every word in a follow-up email? C) Throw a full-blown internal tantrum about being a “bill collector”?

Good news — you don’t have to pick.

The reality? Failed payments are common, expected, and 100% solvable (without sacrificing your energy or vibe).

Our Old Way (Spoiler: It Wasn’t Cute)

Once upon a time, at The Social Bungalow, we handled failed payments like this:

  • Email #1: Sweet and hopeful
  • Silence
  • Email #2: Supportive, a little firmer
  • Awkward explanation or no reply
  • Email #3: Gently direct
  • Ghosted (again)

It was time-consuming, emotionally draining, and honestly? A little too much like chasing people down for gas money.

The New Way (Automation Meets Boundaries)

Here’s how we upgraded — and increased recovered payments by 120%.

Step 1: Automatic Reminder (Day 1)

A pre-written, automated email is sent via our checkout software (we use ThriveCart) as soon as a payment fails.

Most of the time? It’s a simple card update situation and resolves itself immediately.

Step 2: Enter the Follow-Up Workflow (Day 2)

If payment is still outstanding after 48 hours:

  • A Zapier automation tags the client into two places: a tracking spreadsheet and an ActiveCampaign email automation.
  • They enter a 3-email sequence, spaced 60 hours apart:
    • Email 1: Heads Up! + How Can We Help?
    • Email 2: We Tried Again, Let’s Chat
    • Email 3: We’ll Be Revoking Access in 24 Hours (but we’re here if you’d like to resume)
  • Once the payment goes through, they’re automatically removed from the sequence.

No awkward manual follow-ups required.

Step 3: Internal Tracking

A simple spreadsheet logs overdue payments, helping us:

  • Spot patterns
  • Refine payment plan structures if needed
  • Reach out personally if repeat issues arise

Why This Works (Without Feeling Gross)

This system is about:

  • Respectfully reminding clients without shame
  • Protecting your energy
  • Creating clear, compassionate boundaries

It’s structure without sacrificing the client relationship.

And since implementing this? We’ve recovered 120% more payments without turning into part-time debt collectors.

Pro Tips for Smooth Payment Plans

  • Always outline payment terms clearly (contract, client handbook — you choose)
  • Automate what you can, but stay human in your touchpoints
  • Consider early payoff options for clients who want to clear their balance after getting results

Remember, you didn’t build an online business to spend your time chasing credit card declines.

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Hi, I'm shannon!

Founder of The Social Bungalow & Online Business Strategist Helping Creatives and Coaching Entrepreneurs 'Make It' Since 2018

From climbing the corporate ladder to full-time serial entrepreneur and 7-figure business builder, I’m here to share the strategies that make entrepreneurship and small business growth feel doable (and dare I say, fun). Grab a seat, get comfy, and let's make this the year your small business goes big!

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