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Lifecycle Email Strategist · SaaS Retention

I stop your trial users
from going quiet.

Most SaaS products lose 60 to 70% of trial users before they ever see what the product can do. Not because the product is bad. Because nobody guided them through the door. I fix that leak.

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60–70%
Avg. trial drop-off rate
7
Emails in sequence
39.48%
Open rate achieved
4
HubSpot certifications
About

Product thinking,
applied to email.

Most SaaS products lose 60 to 70% of trial users before those users ever see what the product can do. Not because the product is bad. Because nobody guided them through the door.

That's the problem I solve.

I'm Samuel Ajayi, a lifecycle email strategist for early-stage B2B SaaS teams. I build behavior-driven email flows that move users from "just signed up" to actually paying. Welcome sequences, onboarding nudges, trial-to-paid conversion emails, re-engagement campaigns, and retention flows, all written for one person, not blasted at 1,000.

"My edge is in how I think before I write. I spent years in UI/UX design, which means I map where users go quiet, what's confusing them, and which email at which moment removes that friction. It's product thinking applied to email strategy."

Here's what I've built: A 7-email trial-to-paid lifecycle sequence for a B2B SaaS productivity tool, targeting 45 to 55% open rates on welcome emails and 8 to 12% trial-to-paid conversion across the full flow. Every email in the sequence is mapped to specific user behaviors, with subject line rationale, send-time logic, and a metrics framework built in from the start.

I hold HubSpot certifications in Email Marketing and Digital Marketing.

If your onboarding or trial emails aren't converting, I'd like to look at them.

Available to start immediately.

Edge 01

UX-Informed Strategy

Years of UI/UX design means I audit every email like a product screen, mapping friction, drop-off moments, and behavioral triggers before writing a word.

Edge 02

Behavior-Driven Flows

Every sequence I build is triggered by what users actually do, not just time-based sends. The right message, to the right user, at the right moment.

Edge 03

Metrics-First Thinking

I assign conversion goals to every email before launch. Open rates are vanity. Activation rate, trial-to-paid conversion, and win-back rate are what move MRR.

Services

What I build
for SaaS teams.

Specialized lifecycle email services for early-stage B2B SaaS companies with 500 to 10,000 trial users.

01

Trial-to-Paid Lifecycle Sequences

Full 7 to 14 email behavior-driven sequences guiding users from signup through activation, engagement, urgency, and conversion. Every email mapped to a specific user moment with its own CTA and metric goal.

Core Service
02

Onboarding Email Flows

Welcome sequences designed around your product's aha moment. Behavior-aware flows that remove the specific friction points causing users to go quiet before Day 3.

High Impact
03

Re-engagement Campaigns

Mid-trial check-ins and dormant user campaigns that surface objections before it's too late. Built to invite response, not just clicks. Friction you can't see is friction you can't fix.

Retention
04

Win-back and Expiry Flows

Last-chance urgency sequences and post-trial win-back emails that recover non-converters. Includes feedback loops that turn lost trials into research data for the next iteration.

Revenue Recovery
05

Lifecycle Email Audit

A 3-layer audit: journey mapping to find silent drop-off points, trigger audit for behavior vs time alignment, and a metrics framework review against SaaS benchmarks.

Strategy
06

Metrics Framework Setup

Build a measurement system into your email sequences from day one. Track what actually moves MRR: activation rate, trial-to-paid conversion, win-back rate, not just opens and clicks.

Analytics
My Process

The 3-Layer
Lifecycle Audit.

01

Journey Mapping

Before writing a word, I map your user journey end-to-end. Where do users go quiet? What moment causes the activation drop-off? Every email starts here, not at a blank page.

02

Trigger Audit

Are your sends firing at the right moment? I convert time-based sends to behavior-based ones and map each email to a specific user action rather than a calendar date.

03

Metrics Framework

I assign a primary metric, benchmark, and diagnostic signal to every email before launch. Open rate is not a success metric for a trial-to-paid email. Conversion rate is.

04

Copywriting and Build

Every email has one job. One CTA. One message. Copy that feels like it was written for one person, delivered with full strategy notes, subject line rationale, and send-time logic.

Tools I work with
Customer.io
Klaviyo
HubSpot
GoHighLevel
Notion
Figma
Google Analytics
ClickUp
Core competencies
Lifecycle Marketing
Email Copywriting
Customer Onboarding
Email Marketing
Marketing Automation
Retention Marketing
Segmentation
SaaS Marketing
Inbound Marketing
CRM Marketing
Conversion Rate Optimization
Campaign Analytics
Customer.io
HubSpot
Klaviyo
Google Analytics
Gohighlevel
A/B Testing
User Journey Mapping
User Research
Digital Marketing
Remote Collaboration
Stakeholder Communication
Portfolio Work
Case Study · 2026

FlowDesk — Trial-to-Paid Email Flow

A full 7-email behavior-driven lifecycle sequence for a B2B SaaS productivity tool targeting early-stage startup teams, built with full copy, strategy rationale, send-time logic, and a metrics framework for every email in the 14-day trial window.

7
Emails in sequence
14
Day trial window
B2B
Business model
SaaS
Industry focus
The Email Sequence
Metrics Framework
EmailPrimary MetricBenchmarkWhat It Tells You
01 WelcomeOpen Rate50 to 70%Subject line and sender trust
02 Invite TeammateClick Rate15 to 25%Activation intent
03 Social ProofClick Rate10 to 20%Feature interest
04 Check-inReply Rate3 to 8%Friction and objections
05 UrgencyFeature Page Clicks15 to 25%Purchase consideration
06 Last ChanceUpgrade Conversion5 to 15%Direct revenue impact
07 Win-backReactivation / Reply2 to 5%Win-back potential
Experience

Where I've
built this.

Jan 2026 — Present
Self-Employed
Freelance
Lifecycle Email Strategist
  • Designed and built a full 7-email, 14-day trial-to-paid lifecycle sequence for a B2B SaaS productivity tool, targeting 45 to 55% welcome open rate, 8 to 12% trial-to-paid conversion, and 15 to 20% win-back rate
  • Approach: map the user journey first, identify where users go quiet, build sequences that address each friction point with the right message at the right time
  • Every email delivered with full copy, subject line rationale, send-time logic, CTA strategy, and a metrics framework with benchmarks
  • Tools: Customer.io · Klaviyo · HubSpot · GoHighLevel · Notion
Jun 2025 — Present
Pollard Learning, Ontario, Canada (Remote)
Freelance
Virtual / Executive Assistant
  • Managed 50+ outbound email campaigns via GoHighLevel CRM across a contact base of 4,832, achieving a 39.48% open rate, nearly double the industry benchmark of 21%
  • Maintained an engaged subscriber base of 2,113 through disciplined campaign scheduling and audience segmentation
  • Published 8+ social media posts per week, sustaining a content cadence across channels
Jun 2024 — Nov 2025
Nova Tokens, Lagos, Nigeria (Remote)
Freelance
Lead Product Designer
  • Designed 8+ web screens and full mobile counterpart covering wallet flows, payment UX, and trust mechanisms for a Web3 freelancing ecosystem
  • Architected user onboarding and activation flows, the exact same diagnostic thinking I now bring to lifecycle email strategy
  • Conducted user research and journey mapping to identify where users dropped off and why
  • Mentored 4 designers across Nigeria on design systems and career development
Aug 2024 — Apr 2025
Morenikeji Foundation, Lagos, Nigeria
Contract
Virtual / Executive Assistant
  • Authored 2 funding proposals and donor-facing impact reports, demonstrating structured written communication and stakeholder messaging skills
  • Managed correspondence with external donor organizations ensuring audience-aware, data-compliant communication
Dec 2023 — Apr 2024
TossPaper, Ontario, Canada (Remote)
Freelance
Junior Product Designer
  • Designed and tested interfaces for an AI-driven platform, identifying friction points that improved overall workflow efficiency
  • Contributed to end-to-end prototyping and user testing, translating user feedback into actionable design decisions
Education
Mar 2019 — Sep 2024
Bachelor of Science — Sociology and Anthropology
Obafemi Awolowo University, Ile-Ife
Second Class Upper Division
Certifications

Verified expertise
from HubSpot Academy.

HubSpot Academy
Email Marketing Certified
Valid: Feb 2026 — Mar 2028
HubSpot Academy
Inbound Marketing Certified
Valid: Mar 2026 — Apr 2028
HubSpot Academy
Email Marketing Software Certified
Valid: Mar 2026 — Apr 2027
HubSpot Academy
Digital Marketing Certified
Valid: Feb 2026 — Mar 2027
Google
Google Analytics Certified (GA4)
Valid: Apr 2026 — Apr 2027
Work Together

The drop-off is always in the same three places. I already know where yours is.

Most early-stage SaaS teams send the same onboarding emails to every trial user, then wonder why paid conversion is flat. I map where your sequence loses people and rebuild the logic that converts them.

You can reach me by clicking the LinkedIn button below to send a DM, or reach out directly via email. I read every one.

DM me "CHURN" on LinkedIn ajayi.samueloluwakayode@gmail.com