The playbook that worked

1. Services to product
   Use consulting revenue (Price Intelligently) to fund software. Launch ProfitWell Metrics as a free analytics product. That freemium wedge created broad distribution and trust, which later made it easier to upsell revenue products. Metrics is still offered free.

2. Own an audience
   ProfitWell did not rely on ads alone. They built a media engine, the Recur Network, with shows like Pricing Page Teardown and Protect the Hustle. It gave them persistent reach, lowered CAC, and sustained thought leadership around pricing and retention.

3. Monetize the pain
   The revenue products mapped to subscription pain points: Retain for failed‑payment recovery and dunning, Recognized for revenue recognition, and the original Price Intelligently services. Retain aligned monetization directly with recovered revenue.

The outcome

In May 2022, Paddle acquired ProfitWell for $200M in cash and equity and integrated the products into its SaaS revenue platform. Patrick became Paddle’s Chief Strategy Officer after the deal.

In 2024, Paddle divested Price Intelligently to SBI. Metrics and Retain remain within Paddle.

Why the ProfitWell story still matters

Payment failures are persistent. Involuntary churn from failed renewals is still one of the highest ROI problems to fix in subscriptions. Modern billing stacks such as Stripe and Paddle now ship machine‑learning powered smart retries out of the box. That raises the bar for standalone tools and shifts the battleground to precision: classification of failure reasons, retry timing, messaging, and fallback funding sources.

Paddle Retain is pitched as plug‑and‑play payment recovery, cancellation flow optimization, and proactive dunning, now tightly integrated with Paddle Billing. If you buy Paddle, Retain is a logical add‑on.

Where we at FlyCode differ in 2025

https://www.flycode.com/flycode-vs-profitwell-by-paddle-retain

ProfitWell, now Paddle Retain, validated the category. Our view is that the next leg of improvement comes from AI‑first orchestration across the entire failure‑to‑recovery path, especially for high‑growth SaaS where a fixed ruleset leaves money on the table.

How FlyCode’s approach is different:

• Adaptive retry modeling
  Move from fixed schedules to per‑customer and per‑issuer strategies that incorporate decline code, issuer behavior, seasonality, balance‑cycle signals, and historical success windows. Think of an ML controller that changes plan mid‑flight.

• Failure‑reason intelligence
  Classify hard vs soft declines in real time and route actions accordingly: instant card updater for expiries, timed reattempts for insufficient funds, or alternative rails when the issuer is degraded.

• Backup funding and routing
  Proactively surface alternate cards on file and support dynamic routing where your stack allows it, lifting approval rates without extra friction.

• Coordinated outreach
  Trigger the right message by channel based on predicted fix likelihood and local time, with one‑tap secure update flows. Customers solve the problem quickly instead of churning after a poor dunning experience. Best practice pairs smart retries with targeted communication.

• Closed‑loop learning
  Every recovery attempt, including success or failure, cost, time to recovery, and post‑recovery tenure, feeds the model so the next attempt is smarter. Over time that compounding loop matters more than any single tactic.

Bottom line: Paddle Retain made recovery accessible and integrated. FlyCode is built to push recovery beyond generic smart‑retry defaults, with more signals, tighter orchestration, and a learning loop tuned to your customer base.

Lessons operators can copy from ProfitWell and apply now

• Create your own distribution. Services funded their product, and media turned brand into a growth asset. Do not rent your audience. Own it.

• Make the wedge irresistible. A strong free tier such as Metrics earned install base and data, which later powered paid offerings.

• Align pricing with value moments. Charging on recovered revenue feels fair and makes procurement easier.

• Keep optionality. A services arm kept them close to the problem and funded product bets. Divesting later simplified focus.

If you are evaluating retention tools in 2025

1. Start with your baseline: what percent of MRR is lost to involuntary churn, by payment method, issuer, country, and decline code.

2. Check your native stack first: turn on ML smart retries in your billing platform, then quantify the lift.

3. Go deeper where it pays: look for granular failure classification, issuer‑aware retries, coordinated outreach, alternate‑card fallback, and learning loops.

4. Insist on transparency: recovery reporting should reconcile to your ledger and show net lift after fees and commissions.

5. Pilot side by side: run a clean A/B across comparable cohorts and measure net recovered revenue and post‑recovery tenure, not just immediate approvals.

Disclosure: ProfitWell, now part of Paddle, operates in the same space as FlyCode. We respect what they built, and we believe our AI‑first approach is the better fit for where retention is headed.