After leading lifecycle programs for 10+ years and working across brands like Peloton, Casper, Thirty Madison, and more, I’ve seen what makes lifecycle marketing teams successful and the mistakes that derail their efforts. The core issue boils down to this: Many programs are built around what teams need to send to hit internal goals — not on the user behaviors they’re trying to drive.
It sounds like a subtle difference, but it creates two completely different outcomes. Designing for internal benchmarks leads to short-term lifts, calendar-driven campaigns, and constant pressure to get a send-out. But orienting around user behaviors is the key to long-term retention, habit building, and durable LTV.
In this post, I’ll show you how to avoid the first path and build for the second.
The reactive sending trap
When I first stepped into lifecycle marketing, I thought my job was to hit weekly, monthly, and annual conversion numbers. That meant pulling whatever levers I had — like batch emails, limited-time offers to create urgency, discounts, etc. — all in an effort to drive opens, clicks, and conversions. In the short term, this worked. But over time, I began to realize that this mindset has a fundamental flaw. It builds a system where teams chase short-term conversions at the expense of long-term value.
Once organizations see quick wins from this approach, pressure builds from leadership and lifecycle teams are just asked to send more and more. The strategy becomes entirely reactive, driven by calendar deadlines and KPIs, rather than actual customer behavior and value. Teams fall into a cycle of scrambling to create a new campaign week after week, and users start to feel those cracks.
The hidden cost of a reactive lifecycle program
Once reactive sending becomes the default, it quietly starts to break the systems around it:
- Everyone gets the same message, regardless of where they are in their journey
- Batch sends override or conflict with existing flows
- Discounts become the go-to tool to drive engagement, and offers begin to dilute perceived value and do the work your product should have done
- Metrics begin to flatten over time as consumers get fatigued, reducing LTV
- Testing disappears, and insights aren’t captured
- Journeys go stale because teams are so busy launching campaigns, they can’t revisit or optimize the flows that actually move the needle.
- Teams lose visibility into what’s live and what’s actually working, and when something breaks, no one knows how to fix it
This short-term mindset might seem effective at first, but give it 6 to 12 months, and you’ll often see sharp drops in engagement and diminishing returns on conversion. Reactive sends might get you a few golden eggs today, but if you pull the same lever too many times, you’ll inevitably kill your golden goose.
To escape the reactive sending cycle, teams need to adopt a proactive, customer-first strategy. That means designing programs around the customer journey and delivering value at every step, not just driving short-term clicks.
Shifting from reactive to proactive sends
Lifecycle marketing should solve problems, shape habits, and build trust. When you lead with value, retention naturally follows. The goal is not just to send messages, but to deliver meaningful experiences that reinforce behavior and deepen relationships over time. This means mapping out the customer journey and intentionally designing lifecycle experiences that feel timely, useful, and aligned to customer needs.
The best programs I’ve seen treat calendars and journeys as complementary tools, not competing ones. That means calendar sends are built around and alongside the customer journey.
Great lifecycle marketing starts with user behavior and context, and great campaigns feel like a continuation of the product experience, not an interruption. In practice, this means:
- Journeys should drive behavior: Use them to shape long-term habits, reinforce key actions, and guide users through critical moments like onboarding, reactivation, or expansion. They should trigger off real behaviors and feel like a natural extension of the product, not a marketing campaign.
- Batch sends should reinforce behavior: Use them to educate, re-surface value, drive seasonal urgency, or celebrate community moments. They support your program, but should never override it.
- Channels should influence behavior: Use them intentionally to match the message to the moment. For example, Push and SMS are great for urgency or daily nudges; email and in-app work better for storytelling, education, or deeper engagement.
This approach unlocks:
- Higher retention by reinforcing the right behavior early
- More efficient monetization with less reliance on coupons and discounts
- Stronger trust through relevant, well-timed messaging
When you architect your program around customer behavior, you move from reactive execution to a compounding strategy that drives sustainable growth, stronger loyalty, and higher LTV. A great program feels human, relevant, and useful. It adapts to where the user is in their journey. A weak program feels like noise, disjointed, repetitive, or misaligned with user intent.
Building a proactive lifecycle program
Shifting from a reactive send approach to a proactive one changes everything from how you write, how you sequence, when you send, what channels you use, and even what success means.
Here’s the mental model I use when mapping out lifecycle programs:
- Build journeys around behavior, not calendars: Your flows should respond to what customers actually do, not what your internal calendar says. Use actions, milestones, and signals as the trigger for value, not send dates.
- Map messages to retention and LTV-driving behaviors: Don’t just send to send. Start by identifying the habits and behaviors that correlate most with long-term value, then design journeys that reinforce and reward them. Note that these behaviors are different for every company, so don’t just copy and paste what works for another brand.
- Measure what matters: Track the habits and behaviors that lead to your core KPIs — not just opens and clicks. Prioritize metrics like repeat rate, time-to-value, and product engagement (or whatever is most relevant to your core business goals).
- Protect automations from batch overrides: Ensure high-value flows are not interrupted by high-volume campaigns. Set up exclusions and smart targeting logic so journeys can run their course without interference.
- Balance batch sends and journeys strategically: Batch campaigns still play a valuable role, especially for new launches, promotions, or re-engagement. They should complement evergreen flows, not replace them.
- Test and iterate with purpose: Each message is a chance to learn. Set clear hypotheses, measure incrementality, and use those learnings to evolve the program. Proactive does not mean static.
It’s worth it to really sit back and think about the customer experience you’re delivering. Doing so forces you to architect your program around customer behavior and move from reactive execution to a compounding strategy that drives sustainable growth, stronger loyalty, and higher lifetime value.
Securing internal alignment
It’s also important to acknowledge the reality: making this shift isn’t easy. Many organizations already have deep momentum around campaign calendars, internal KPIs, and “just get it out the door” mindsets.
Breaking that cycle takes deliberate re-education of your team, your stakeholders, and even your partners. You’ll need to show why behavior-first programs compound over time, why protecting automations matters, and why not every metric is worth chasing.
The good news is that you don’t have to flip the switch all at once. Start small and focus on small, but measurable wins. That’s what builds buy-in. Over time, this shift turns the lifecycle from a campaign factory into a growth engine that everyone in the organization can rally behind.
