Designing a Cross-sell and Free Trial Activation Email Strategy

This case study reflects anonymized work performed in a healthcare technology context. Company name, product details, and internal systems have been intentionally omitted. Metrics are rounded and directionally representative. This case study is shared solely to demonstrate strategic thinking and execution approach.

Context

A healthcare technology company launched a new product designed to both attract new users and cross-sell to an existing base of professional providers using a core product. Initial launch interest was strong, but within a few months, cross-sell volume declined sharply, signaling that awareness andadoption were not sustaining beyond launch.

As the Marketing Generalist, I was asked to support cross-sell performance — despite the fact that marketing had historically been limited to existing customers.

Problem

Cross-sell performance declined after the initial launch window
Existing customers were not receiving consistent re-engagement touchpoints
Adoption relied on passive interest rather than intentional lifecycle design
There was no structured cadence to support awareness, trial, or conversion

Constraints

The organization had historically relied on passive communications to market existing customers.
Audience was clinical and professional, requiring high trust and low sales pressure
Risk of over-communication and potential trust erosion if cadence was misjudged

Strategy

I led a consistent and company-first customer email cadence focused on re-engaging and marketing existing customers and driving behaviors: starting a trial of the cross-sell product, and encouraging for them purchaseafterwrds

Stage 1: I intentionally started with a simple approach to test the engagement of marketing emails.

1-2 emails per month
Testing different messaging angles (e.g. direct sales framing vs. educational/value-led content)

Stage 2: Once traction was established, I introduced behavioral segmentation to improve message relevance, including:

Length of customer tenure
Additional emails for recently trialed customers and email openers

Stage 1: Validation

📧 Cadence

1-2 emails per month

🎯 Messaging Tests

Direct sales vs. Educational content

↓

Stage 2: Behavioral Segmentation

👤 Tenure

Length of customer relationship

🔬 New Product Trial Status

Tried vs. not tried product

📊 Engagement

Customers recently tried the new product and email openers get additional touchpoints

Key Decisions

Balancing Cadence and Trust. I faced hesitation around the risk of over-communicating — particularly given that customers had not previously received marketing emails. To manage this, I closely monitored unsubscribe rates and engagement metrics, adjusting cadence and tone to strike the right balance between consistency and trust.
Segmented based on real behavior. After trial volume increased, I split the audience into: customers who had tried the upsell product and customers who had not. This allowed subsequent messaging to reflect readiness andavoid redundancy.
Used performance data to influence business decisions. When the free trial was removed due to a shift in business direction, I monitored performance and identified a significant drop in trial and training sign-ups. I brought this data to cross-functional stakeholders, which contributed to the decision to reintroduce the free-trial incentive in a later cycle.

Outcomes

Free trial sign-ups increased from ~70 to 200+ within one month after the cadence launched.
Monthly deals rebounded, reaching 120 conversions in a single month after a period of decline.
Message testing identified a high-performing format — customer and expert testimonial-led emails, with one email driving 4.3% conversation rate.
Segmentation improved engagement quality and created a foundation for future lifecycle programs.
Performance data contributed to the decision to reintroduce an incentive later in the year to protect cross-sell momentum.
Performance data was shared with cross-functional stakeholders and informed subsequent experimentation with incentives.

Free Trial Sign-ups

70 → 200+

📈 +186% increase

Monthly Conversions

120 deals

📈 Peak month performance

High-Performer

4.3% Converstion Rate

🏆 Expert video and testimonial email