Senior Customer Success Manager · CS Leader · Enterprise AMER

Olabisi
Owolabi

I build the infrastructure that makes retention predictable. Health frameworks, playbooks, and the systems that turn customer success into a revenue function rather than a support ticket.

Years enterprise CS

120%

Net revenue retention

$25M+

Portfolio managed

35%

Churn reduction

How I think

My customer success philosophy

CS is a revenue function

Retention and expansion are commercial outcomes, not service metrics. Every interaction builds toward a renewal that should feel inevitable rather than urgent.

Retention starts at onboarding

The renewal is won or lost in the first 90 days. How a customer is onboarded, what success looks like to them, and whether they feel genuinely partnered — that is where churn decisions begin.

Data before instinct

Health scores, usage signals, and commercial indicators tell you what is coming before the customer does. Gut feel is the last line of defence, not the first.

Know their industry, not just their account

A great CSM knows the product. An exceptional one knows the customer's competitors and market pressures. That is what earns a seat at the strategic table.

Build systems, not habits

Relationships are personal. Retention is structural. The best CS functions do not depend on any one person. They run on playbooks, health frameworks, and escalation processes that outlast the individual.

Honest conversations keep accounts

Customers do not leave because you told them a hard truth. They leave because you did not. The CSMs who retain the most are the ones willing to have the difficult conversation first.

Free diagnostic

Is your CS infrastructure actually working?

Five questions. Two minutes. An honest read on whether your customer success setup is built to retain or built to react.

CS Infrastructure Score

Want to talk through what this means?

I review these results personally. If something here resonates or concerns you, I am happy to have a real conversation about what it actually looks like to fix it.

Email Olabisi

Where I have worked

Experience as a CSM and customer success leader

2025 — Present

Remote

Customer Success Manager, Global EOR

Managing enterprise and mid-market accounts across AMER in one of the most compliance-heavy environments in SaaS — global employment across 90 plus countries. I navigate multi-jurisdictional employment law, payroll escalations, and complex legal disputes on a daily basis. I lead renewal negotiations from commercial discussion through to signed order form, and work closely with legal, payroll, and product teams to resolve situations that most CSMs would escalate immediately.

EORGlobal compliance Enterprise AMERRenewal ownership Payroll escalation

2021 — 2025

Capita

Senior CSM and Team Lead

Managed a $25M plus enterprise portfolio to 120% NRR. Built the CS team of five from scratch, including the health framework, QBR programme, renewal playbook, and escalation process. Reduced churn by 35%, cut onboarding time by 30%, and drove 45% higher feature engagement. Three team members were promoted within 12 months.

$25M+ portfolio120% NRR Team leadershipCS infrastructure

2019 — 2021

Enterscale

Customer Success Lead

Maintained 95 plus percent client satisfaction across the portfolio. Redesigned the onboarding programme with Product, reducing early-stage churn by 25%. Cut support ticket volume by 15% through proactive training and tighter feedback loops between CS and Product.

Onboarding designChurn reduction Product collaboration

2016 — 2019

X3M Ideas

Customer Engagement and Retention

Led retention and loyalty programmes for global regulated brands including Pernod Ricard and British American Tobacco. Managed high-visibility audience engagement for Big Brother Africa. Used customer analytics to improve engagement metrics by 18% across key client segments.

LagosGlobal brands Retention strategy

Background

About Olabisi Owolabi

I am Olabisi, originally from Lagos and now based in Calgary, Alberta. I started my career running campaigns for global brands at X3M Ideas, which is where I learned that the most important part of any client relationship is what happens after the sale.

I hold an LL.B in law, evaluated as a Canadian equivalent. It gives me a real edge in the compliance-heavy, legally complex conversations that come with enterprise accounts. I do not need a legal team in the room to read a contract or understand what is actually at stake.

I founded Ritenly because I kept watching great products lose customers not from product failure but from missing infrastructure. No health scoring, no escalation playbook, no onboarding framework. I built Ritenly to fix that for founders who cannot yet afford a full CS team.

Outside of work I am a mother of two, curious about organisational psychology, and someone who believes a well-designed space is not a luxury — it is how you show up clearly.

Core expertise

Enterprise account management · Customer health score frameworks · QBR design · Renewal ownership · Churn reduction · Expansion strategy · Onboarding frameworks

Compliance and legal

Multi-jurisdictional employment law · EOR operations · Co-employment risk · Contract negotiation · LL.B (law)

Leadership

Team building · Coaching · Playbook development · CS infrastructure design · Peer mentorship

Tools

Salesforce · Gainsight · Vitally · Workato · HubSpot · Gong · Notion · Claude

Based in

Calgary, Alberta, Canada · Open to remote roles globally

Connect

LinkedIn · Email

Also building

Ritenly

CS infrastructure for SaaS founders who are serious about retention

Great products lose customers not from product failure but from missing foundations. No health scoring, no QBR programme, no escalation playbook. Ritenly builds that infrastructure for founders at the $500K to $2M ARR stage who cannot yet afford a full CS team. We build the system and hand you the keys.

Learn more about Ritenly

$500K–$2M

ARR stage we serve

6 weeks

Done-for-you Retention Sprint

$80K+

Revenue at risk per year at $1M ARR with 8% churn

Questions people ask

Frequently asked questions

Who is Olabisi Owolabi?

Olabisi Owolabi is a Senior Customer Success Manager (CSM) and customer success leader based in Calgary, Alberta, Canada. She has 8+ years in enterprise B2B SaaS, currently manages enterprise and mid-market accounts across AMER at Remote, and is the founder of Ritenly, a studio that builds customer success infrastructure for SaaS founders. She holds an LL.B in law, evaluated as a Canadian equivalent.

What does Olabisi Owolabi do as a Senior CSM?

She owns enterprise and mid-market accounts end to end: adoption, health scoring, escalation, expansion and renewal negotiation through to signed order form. At Capita she also built a CS team of five from scratch, along with the health score framework, QBR programme and renewal playbook behind it.

How do you build a customer health score framework?

Start from the outcome the customer bought, not the features they log into. A useful health score blends product usage against expected usage, breadth of adoption across teams, support and escalation history, executive sponsor engagement, and commercial signals like invoice behaviour.

Then automate it from product data so it updates daily. A health score a CSM updates by hand after a call is always one step behind the customer.

How did Olabisi Owolabi reach 120% net revenue retention?

By treating customer success as a revenue function rather than a support function. On a $25M+ enterprise portfolio at Capita that meant an automated health score framework to see risk early, an onboarding programme that cut time to value by 30%, exec-aligned success plans tied to business outcomes, and CSMs who owned the commercial renewal conversation. Churn fell 35% and feature engagement rose 45%.

How do you reduce churn in B2B SaaS?

Retention starts at onboarding. The renewal is usually won or lost in the first 90 days, so the fastest churn reduction lever is a repeatable onboarding framework with a clear first value milestone.

After that it is early-warning health data, documented success plans signed off by an executive sponsor, and honest conversations. Customers do not leave because you told them a hard truth. They leave because you did not.

What is Ritenly?

Ritenly is the CS infrastructure studio founded by Olabisi Owolabi. It builds done-for-you customer success foundations for B2B SaaS founders at the $500K to $2M ARR stage: health scoring, retention playbooks, onboarding frameworks and escalation processes, delivered as a 6-week Retention Sprint. We build the system and hand the founder the keys.

Is Olabisi Owolabi available for CSM or customer success leadership roles?

Yes. She is based in Calgary, Alberta and open to senior CSM, enterprise CSM and customer success leadership roles, including remote roles globally, as well as Ritenly consulting engagements. The fastest way to reach her is owolabi.rolabisi@gmail.com.

Something not covered here? Ask my AI assistant or email owolabi.rolabisi@gmail.com.

OlabisiOwolabi