Customer Marketing Deep Dive

May 11, 2026

Guest

Naomi (Senior Product Marketing Manager, Customer.io)

Guest

Jonathan (VP of Marketing, Seamless.AI)

Guest

Sue (Head of Lifecycle Marketing, Monarch Money)

Naomi, Senior Product Marketing Manager at Customer.io, uses plain-text emails and beta programs to collect replies and shape product direction. Jonathan, VP of Marketing at Seamless.AI, built a 365-day multi-channel engagement program, an AI chatbot that deflected support tickets, and live trainings to cut cancellations. Sue, Head of Lifecycle Marketing at Monarch Money, drove a trial-timed referral test that lifted shares 64% and added big ARR.

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INSIGHT

Promote Referrals During Trial For Bigger Lift

The best moment to promote referrals can be early in a trial, not after conversion.
Monarch found trial-day prompts to users with at least one connected account produced a 64% lift in shares and higher conversion rates.

ANECDOTE

Monarch Scaled Mobile Referral Prompt To Desktop

Monarch expanded a mobile in-app referral prompt to web after realizing 80% of free trials started on desktop.
Desktop pop-up produced a 16% relative lift in shares and ~20% increase in referrals redeemed, equating to ~$500K incremental ARR.

INSIGHT

Turn Customer Engagement Into A 365 Day Program

Stop treating customer engagement as one-off campaigns and bake a 365-day behavioral program into the product experience.
Seamless uses email, in-app, SMS, training, and personalization to trigger messages based on user behavior.

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#354 | Sue (Head of Lifecycle Marketing, Monarch Money), Jonathan (VP of Marketing, Seamless.AI), and Naomi (Senior Product Marketing Manager, Customer.io) join Dan for a live Exit Five session on customer marketing. Sue breaks down how Monarch discovered that the best time to promote their referral program was during trial and the data behind a 64% lift in referral shares and half a million dollars in incremental ARR. Jonathan shares how Seamless.AI stopped treating customer engagement like a campaign and built a full 365-day behavioral program, including an AI chatbot that deflected 55% of support tickets and live trainings that flattened their churn curve. Then Naomi walks through how she uses plain-text emails asking for replies to close the feedback loop on new features and shape the product roadmap.

Timestamps

(00:00) - - Intro
(07:15) - - Sue: Why the best time to promote a referral program is during trial, not after
(10:15) - - The results: 64% lift in referral shares and $500K in incremental ARR
(17:15) - - Sue's background: 16 years in lifecycle marketing from online dating to Calm to Monarch
(20:15) - - Jonathan: Stopping treating customer engagement like a campaign
(26:15) - - Building a 365-day behavioral multi-channel customer engagement program
(27:15) - - The AI chatbot that deflected 55% of support tickets
(35:20) - - Live customer training 4x a week and how it flattened the churn curve
(40:20) - - Growth plays for NRR: marketing to users inside existing accounts
(42:20) - - Jonathan's results: 24% decrease in cancellations year over year
(43:20) - - Naomi: Using lifecycle marketing to close the product feedback loop
(49:20) - - The MCP server onboarding flow and why she asks for replies instead of clicks
(56:20) - - Using beta email campaigns to shape the product roadmap
(59:20) - - Live Q&A

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