Many marketing teams are at different stages of transformation. Some are still unifying data and building foundational journeys. Others have already rolled out personalization, modular content, and AI. But across the board, one challenge remains the same: strategy still has a habit of stalling out — stuck in planning decks and spreadsheets instead of showing up for customers in the moments that matter most.
In the final session of Iterable’s five-part webinar series, we focus on turning planning into performance across the lifecycle. Below, we break down the top takeaways from our conversation with Rachel Kamel (Director of CRM, Zwift), Tanya Littlefield (VP of Growth and Digital Marketing, Amplitude). It starts with a deceptively simple question: Which moments matter?
| For the full deep dive into executing on revenue-critical marketing moments, watch the full session on demand. |
What Makes a Moment Revenue-Critical?
Before teams can improve execution, they need a shared definition of what actually matters. Not every customer interaction deserves the same level of investment, and treating them all the same often slows execution.
Revenue-critical moments are specific actions or milestones that consistently correlate with retention, monetization, or churn. These interactions genuinely change the trajectory of the relationship when a customer decides to stay, spend more, disengage, or leave altogether (especially important in subscription service businesses).Â
Revenue-critical moments aren’t always positive or obvious. Friction points — a stalled setup, confusing features, or poorly timed messages — can erode revenue if ignored. Finding and addressing these often delivers the biggest gains.
Subscription Retention Challenges That Derail Revenue-Critical Moments
Once revenue-critical moments are defined, the next challenge is operational: executing on them consistently in a subscription environment. Unlike one-time conversions, subscription revenue is earned repeatedly, which makes execution failures especially costly.
During the webinar, three recurring challenges surfaced as the most common ways revenue-critical moments get derailed.
1. Stack-Ranking Work When Everything Feels Urgent
Retention initiatives always feel important, and that’s exactly the problem. Lifecycle teams often compete with product, engineering, and data teams for shared resources, so even high-impact work can stall if it isn’t clearly tied to company-wide KPIs like retention or revenue.
Teams that consistently execute on revenue-critical moments rely on clear structure, shared inputs, and disciplined prioritization achieved in a few key ways:
- Standardize how work is proposed: Use consistent one-sheeter templates to define ownership, use cases, dependencies, level of effort, and expected business impact.
- Prioritize by impact, not urgency: Pair stack ranking with an impact-versus-effort matrix so high-leverage lifecycle initiatives can compete fairly with core product work.
- De-risk large initiatives: Break multi-quarter projects into smaller stages to deliver earlier value and create proof points that justify continued investment.
- Size opportunities with data: Use cohort size, past experiment performance, and expected lift to quantify impact and justify scaling successful programs (e.g., loyalty micro-programs showing measurable lift).Â
The result is fewer opinion-based debates and more outcome-driven decisions, where revenue-critical moments consistently rise to the top.
2. Reporting Without Noise — or Delay
Even when the right work gets prioritized, execution can still break down in measurement. Report too frequently, and you’re stuck delivering the same weekly update with no new signal. Wait too long, and you miss the opportunity to optimize a journey or prevent churn altogether.
The teams that get this right treat measurement as an active part of execution by doing the following:
- Building in deliberate check-ins: Automated lifecycle programs still need regular reviews to confirm they’re influencing the intended revenue-critical moment.
- Reporting outcomes, not metrics: Stakeholders care whether it worked, not delivery rates or CTRs. Translate lifecycle performance into business impact for all teams.
- Matching reporting to how decisions get made: Tailor cadence and depth to your organization’s meeting rhythm, audience, and decision process.
3. “Waking the Dead”: When Engagement Messaging Triggers Churn
In an effort to drive usage, teams often send reminders to inactive users, only to unintentionally surface a harsher truth: I’m paying for something I’m not using. As Kamel pointed out, these messages can backfire, prompting cancellations instead of renewed engagement. It’s one of the clearest examples of a negative revenue-critical moment.
To mitigate this risk, teams should:
- Treat cancellations as a core signal, not a lagging metric: Monitor churn alongside engagement metrics to identify when lifecycle communications are actively contributing to subscription loss.
- Target with intent, not volume: Re-engagement should be driven by behavioral signals and readiness, not ramping up messaging to all inactive users.
- Avoid one-size-fits-all reactivation: Not every inactive customer should be prompted to return in the same way — and in some cases, not at all.
How Zwift Aligns Lifecycle Strategy With Seasonal Revenue-Critical Moments
Zwift is a clear example of how subscription businesses can operationalize revenue-critical moments shaped by predictable behavior. As an indoor cycling platform, usage peaks in fall and winter and declines in spring and summer as riders move outdoors — creating recurring, year-round retention risk.
Rather than waiting for cancellations, Zwift focuses on earlier behavioral signals that indicate churn risk, including usage drop-off, fewer app opens, and customers questioning the value of their subscription. From these signals, two priority moments emerge:
- Seasonal disengagement, as riders migrate outdoors
- Feature adoption, where new capabilities reinforce ongoing value
These moments define when lifecycle execution matters most and what must be operationalized to protect revenue:
Aligning Lifecycle Execution to Seasonal Business Rhythms
Zwift plans lifecycle priorities around predictable acquisition and usage cycles. During peak indoor seasons, execution focuses on onboarding, progression, and habit formation. As riders move outdoors, campaigns shift to reinforcing value by connecting indoor and outdoor experiences — not generic “come back” messaging.
Cross-Functional Collaboration for Feature Activation
When Zwift launched outdoor ride tracking, lifecycle execution depended on access to new data like ride events, timing, and experience points (XP). Instead of waiting until launch, the CRM team worked with product and data during development to define these requirements upfront.
“I think that a lot of times there’s an assumption that since the company has the data, [lifecycle teams] must have access to it. I think that our job is to communicate what needs to be built in order for us to have that data.”
~ Rachel Kamel, Director of CRM at Zwift
With the right timing and data in place, Zwift’s lifecycle programs now drive product behaviors that support retention — in some cases extending subscriptions by 30 days or even a full year.
Amplitude’s Data-Driven Principles for Revenue Impact
If Zwift shows what execution looks like in practice, Amplitude shows how to structure teams and feedback loops to sustain it.Â
Rather than organizing by function, Amplitude operationalizes execution through a small set of principles that help teams move faster, learn continuously, and act on retention signals.
- Organize Teams Around the Lifecycle: Cross-functional pods aligned to lifecycle stages bring marketers, product managers, engineers, and designers into shared execution — reducing handoffs and speeding decisions.
- Combine data with direct customer insight: Short, incentivized customer calls (15 minutes, $20 gift cards) supplement behavioral data with context dashboards can’t provide.
- Reuse what already works: By adapting frameworks and experiments that have worked before, teams reduce risk and speed up execution without reinventing the wheel.
- Build shared learning loops: Cross-functional teams can watch real user sessions together to understand and improve how customers actually experience journeys.
Turning Strategy Into Revenue-Critical Action: What To Do and Avoid
Zwift and Amplitude prove the same point: Execution improves when teams focus less on volume and velocity and more on timing, relevance, and impact. Here’s how you can apply these principles to your team:
| Do | Don’t |
|
Anchor prioritization around business impact Engage product, data, and engineering early Combine qualitative insight with quantitative analysis Leverage historical learnings instead of starting from zero Size opportunities with data to justify investment Tailor reporting to stakeholder expectations and cadence |
Assume stakeholders understand lifecycle metrics Report too early without signals, or too late to act Ignore negative revenue-critical moments that cause churn “Wake the dead” with poorly targeted re-engagement Separate content, data, and journey strategy. Treat measurement as set-and-forget |
Putting the Moments-Based Playbook to Work
Execution is where lifecycle marketing delivers business value. Successful marketing teams make revenue-critical moments work for them by focusing on the touchpoints that influence retention and churn, aligning cross-functional resources around them, and translating lifecycle work into outcomes leadership cares about.
This final step completes the Moments-Based Marketing Playbook series. To see the full Step 5 conversation in action, watch the full webinar on demand or explore the complete five-part playbook: The New Era of Moments-Based Marketing: 5 Steps to Evolve Your Marketing Strategy.
