The Loyalty Equation: Leadership Lessons for Enduring Growth

Published by

Iterable

Key Takeaways

  • Customer loyalty is earned through every interaction, not secured through habit or switching costs.
  • The strongest retention strategies help customers achieve their immediate goal before pursuing the next conversion.
  • Loyalty programs should reflect customer behavior and business economics, whether they are tiered, subscription-based, or signal-based.
  • Long-term loyalty grows when marketers measure customer outcomes instead of short-term campaign attribution.

Customer loyalty has never been harder to earn.

Consumers can compare products, prices, and reviews in seconds. AI-powered search makes alternatives easier to discover than ever before, reducing the switching costs that once kept customers loyal by default. Brands can no longer assume a satisfied customer will remain a customer. They have to continue earning that relationship.

That was the central theme of an Activate Summit 2026 session featuring Wendy Bergh, Chief Marketing Officer at Rakuten, and Allison Bernstein, Head of Global CRM at Angie. Rather than focusing on loyalty programs alone, the discussion explored the decisions that strengthen or weaken customer relationships over time. 

From communication frequency to personalization and executive buy-in, both leaders argued that loyalty is the result of consistent customer-first decisions rather than a single retention initiative.

Editor’s note: Watch Wendy Bergh and Allison Bernstein’s full Activate Summit session on demand to learn more about the strategies discussed in this article.

Loyalty Is a Practice, Not a Program

Many loyalty strategies were built for a different era.

Customers once remained loyal because changing providers required significant time, effort, or cost. Today, alternatives are only a few clicks away. According to Allison Bernstein, AI has accelerated that shift by making competing products and services easier to discover. Retention now depends less on convenience and more on the quality of every customer interaction.

Wendy Bergh described loyalty as “earned preference” rather than habit. She shared an experience where a rideshare company quickly corrected a billing issue after a driver made several wrong turns. The mistake did not determine her loyalty. The company’s response did.

Bernstein shared the opposite experience. A grocery delivery company refused to correct an obvious service failure, leaving her to replace the order herself. Years later, she still has not returned as a customer.

Together, those stories reinforce an important principle. Every customer interaction either strengthens or weakens the relationship.

That includes:

  • Marketing emails and promotional messages.
  • Product and website experiences.
  • Customer service interactions.
  • Recommendations and personalized content.

Trust builds through a series of positive experiences, but a single poor interaction can undo years of goodwill. That is why Rakuten evaluates every touchpoint as an opportunity to reinforce the customer’s decision to stay.

Both leaders also challenged a common misconception about personalization. The purpose of personalization is to help customers achieve their goals, not simply create another opportunity to sell.

At Angie, customer data is used to recommend relevant home maintenance projects or connect homeowners with trusted professionals based on factors such as location and the age of their home. Making the experience more useful strengthens trust, which ultimately leads to stronger long-term engagement.

Takeaway: Loyalty is earned through everyday decisions that demonstrate reliability, relevance, and respect for the customer’s needs.

Help Customers Succeed Before You Ask for More

Most marketing teams measure success by the next conversion.

Rakuten and Angie measure something different. Both organizations focus on helping customers achieve the outcome that brought them to the brand in the first place. Only after that objective is complete do they encourage the next action. That sequencing improves both the customer experience and long-term retention.

Each company applies that philosophy differently.

Rakuten focuses on building momentum after a customer’s first purchase.

  • Internal data shows customers who reach a third purchase are significantly more likely to become long-term, loyal members.
  • The team analyzes behavioral cohorts to understand how customers reach that milestone and how similar users can be guided along the same path.

Angie focuses on helping customers complete the job that brought them to the platform.

Homeowners visit Angie because they need to solve a specific problem, whether that means replacing a roof or finding a plumber. Bernstein explained that the marketing team realized it was encouraging additional transactions before customers had successfully completed their first one.

To address that, the team changed its communication strategy by:

  • Reducing promotional messages during the first stage of the customer journey.
  • Waiting up to 16 days before introducing additional offers.
  • Prioritizing matching homeowners with the right service professional before promoting the next transaction.

The change reduced marketing attribution for the CRM team in the short term, but it increased revenue and customer success across the business. Helping customers achieve their immediate goal ultimately created a stronger foundation for future engagement.

Takeaway: Loyalty grows when marketers optimize for customer outcomes before campaign outcomes. Helping customers succeed today creates more opportunities to engage them tomorrow.

Choose the Loyalty Model That Fits Your Business

Not every business should build loyalty the same way.

Bergh outlined three common approaches to loyalty, each designed around a different customer relationship and economic model. Selecting the right structure depends on how customers interact with the business and what behaviors the organization wants to encourage.

The three models include:

  1. Tier-based loyalty programs that reward customers as they spend or engage more. Airlines are a common example, with benefits increasing as members reach higher status levels.
  2. Subscription-based programs where customers pay for ongoing benefits such as faster delivery, reduced fees, or exclusive services.
  3. Signal-based loyalty programs that recognize customer behavior without requiring formal membership tiers. As customers demonstrate loyalty through their actions, brands respond with increasingly personalized experiences and rewards.

Rakuten is currently investing heavily in signal-based loyalty because it allows the company to respond to customer behavior throughout the lifecycle instead of relying exclusively on predefined program rules. Behavioral signals reveal when customers are becoming more engaged, making it possible to reward loyalty as it develops rather than waiting for customers to reach a specific milestone.

Bergh also emphasized that loyalty strategy is a financial decision as much as a marketing one. Each model carries different costs, incentives, and operational requirements. The most effective program is the one that aligns with both customer expectations and the economics of the business.

Takeaway: Loyalty programs should reflect customer behavior and business strategy. The strongest programs encourage the behaviors that create long-term value for both customers and the organization.

Measure Loyalty Beyond Marketing Attribution

Many marketing teams evaluate success through campaign performance.

Open rates, clicks, attributed revenue, and conversions all provide useful signals, but they do not always reflect whether customers are building a stronger relationship with the brand. Rakuten and Angie both argued that loyalty requires a broader view of performance, one that measures customer outcomes over longer periods of time.

Angie Measured Relationship Health, Not Just Campaign Performance

At Angie, that shift began with a simple observation. Traditional email metrics looked healthy, yet customer feedback suggested a very different experience.

An NPS survey revealed that marketing communications had become the second-largest customer complaint. Rather than increasing email volume to drive additional short-term revenue, the team systematically reduced unnecessary communications and evaluated each message based on whether it added value for the homeowner.

That new approach changed how the team defined success.

  • Overall communication volume decreased by approximately 40%.
  • Fewer unsubscribes became a leading indicator of long-term customer value.
  • The team prioritized lifetime engagement over incremental campaign attribution.

Rakuten Used Customer Feedback to Improve the Experience

Rakuten applies the same discipline through continuous experimentation. Bergh described testing as an ongoing practice because customer behavior evolves across segments, channels, and stages of the journey. Regular experimentation helps the team identify which experiences strengthen trust and which introduce friction.

The company also incorporated customer feedback directly into product design. Instead of asking customers what they wanted, the team presented multiple prototype landing pages, gathered reactions, and refined the experience through several rounds of testing.

Customer feedback consistently highlighted three priorities:

  • Guidance.
  • Trust.
  • Value.

The redesigned signup experience reflected those priorities and nearly doubled performance after launch.

Takeaway: Loyalty becomes easier to measure when marketers look beyond campaign metrics. Customer feedback, long-term engagement, and continuous experimentation provide a clearer picture of whether marketing is strengthening the relationship.

Build Trust With Data Before Asking for Buy-In

Customer-first decisions often require organizational support.

Reducing email volume, delaying promotional messages, or investing in long-term retention can appear risky when viewed through short-term performance metrics. Bernstein explained that gaining executive support requires more than a compelling argument. It requires evidence that demonstrates how those decisions will improve the business over time.

At Angie, that evidence came through structured experimentation. Before expanding major program changes, the team built financial models, created dashboards to compare projected and actual performance, and ran multiple rounds of testing. Those results gave leadership confidence that lower attributed revenue in the short term would translate into stronger customer outcomes and greater long-term value.

Bernstein also emphasized the importance of understanding the perspective of executive stakeholders. A chief executive is responsible for protecting the business, which means major strategic changes require clear evidence and thoughtful risk management. Building that evidence before requesting approval makes it easier for leadership teams to support decisions that prioritize long-term customer relationships over immediate campaign results.

The same principle applies to loyalty strategy as a whole. Trust grows when organizations consistently use customer insight, experimentation, and measurable outcomes to guide decisions. Those practices strengthen relationships with customers while also creating confidence inside the business.

Takeaway: Long-term loyalty strategies gain traction when marketers pair customer insight with measurable evidence. Data builds confidence, reduces organizational risk, and helps leaders invest in decisions that create lasting customer value.

Loyalty Is Built Through Everyday Decisions

Loyalty is often associated with rewards programs, discounts, and incentives. The discussion between Wendy Bergh and Allison Bernstein presented a broader perspective. Customers remain loyal because brands consistently demonstrate that they understand their needs, respect their time, and deliver on their promises.

Those principles influence every stage of the customer relationship. They shape how marketers personalize experiences, when they choose to communicate, how they measure success, and how they evaluate long-term performance. The strongest loyalty strategies are supported by continuous testing, customer feedback, and operational decisions that prioritize customer outcomes over short-term marketing metrics.

As customer expectations continue to evolve, those disciplines become increasingly important. Brands that earn trust through every interaction create stronger relationships, improve retention, and build a competitive advantage that extends well beyond any single loyalty program.

Editor’s note: Watch Wendy Bergh and Allison Bernstein’s full Activate Summit session on demand to hear more about the strategies behind today’s most effective loyalty programs.

Frequently Asked Questions (FAQs)

What creates long-term customer loyalty?

Long-term loyalty develops through consistent positive experiences that reinforce trust over time. Every interaction gives customers another reason to continue the relationship or explore alternatives.

What is signal-based loyalty?

Signal-based loyalty recognizes and responds to customer behavior instead of relying exclusively on formal tiers or memberships. Brands use behavioral signals to deliver increasingly relevant experiences as customers become more engaged.

Why did Angie reduce its marketing communications?

Customer research showed that communication volume had become a source of frustration. By reducing unnecessary messages and focusing on helping homeowners complete their initial project, Angie improved long-term customer outcomes while creating more value across the business.

Why is long-term measurement important for loyalty?

Short-term campaign metrics do not always reflect whether customers are becoming more loyal. Measuring engagement, retention, customer feedback, and lifetime value provides a more complete understanding of relationship health.

How can marketers gain executive support for long-term loyalty initiatives?

Build the business case with data. Structured testing, financial modeling, and measurable results help leadership understand the long-term value of customer-first decisions and reduce the perceived risk of strategic change.