Senior Customer Success Manager · AMER · Remote

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.

8+
Years enterprise CS
120%
Net revenue retention
$25M+
Portfolio managed
35%
Churn reduction

How I think

My CS philosophy

01
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.
02
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.
03
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.
04
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.
05
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.
06
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

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

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CS Infrastructure Score
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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.
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Industries and domains

Experience

Global Employment and Compliance
Managed enterprise accounts across AMER in one of the most compliance-heavy environments in SaaS. Navigated multi-jurisdictional employment law, payroll disputes, and high-stakes legal situations daily. Led renewal negotiations from first commercial conversation through to signed order form.
EORMulti-jurisdictional lawRenewal ownershipEnterprise AMER
Enterprise SaaS and Managed Services
Built a CS team of five from scratch and managed a $25M plus portfolio to 120% NRR. Reduced churn by 35 percent, cut onboarding time by 30 percent, and drove three promotions within 12 months. The kind of environment where you learn fast or fall behind.
$25M+ portfolio120% NRRTeam leadershipCS infrastructure
Workforce Management and Field Operations
Managed enterprise accounts and a large digital customer base simultaneously across security and field operations. Built the health framework, escalation playbook, and coaching programme for a team of four CSMs who consistently hit 110 percent of quota.
EnterpriseDigital scaleHealth frameworksTeam coaching
Blockchain and Decentralised Technology
Worked with a web3 company building a token-based WiFi sharing network across IoT and mobile infrastructure. Ran the full engagement from business audit through to go-to-market strategy. Learned early that the hardest part of blockchain is not the technology. It is making it make sense to real people.
Web3Token economyIoTGo-to-market
PaaS and Cloud Application Platforms
Worked in managed cloud environments built for developer and DevOps teams. Developed a working understanding of how infrastructure-level platforms create value and how to translate that into language executives actually care about.
PaaSCloud infrastructureDevOpsTechnical translation
Marketing and Brand — West Africa
Ran retention and loyalty programmes for global regulated brands across Lagos. Managed audience engagement for one of Africa's biggest television formats. Where I learned that understanding what keeps people coming back is the same skill regardless of the industry.
LagosGlobal brandsRetention strategyConsumer engagement
CS Infrastructure
Built retention systems from scratch including health scoring, playbooks, onboarding frameworks, and escalation processes for companies that needed the infrastructure before they could afford the team. This is the thread running through everything above.
Health scoringPlaybooksOnboarding designRetention systems

Background

About me

I am Olabisi, originally from Lagos, now based in Calgary, Alberta. I started my career running campaigns for global brands at X3M Ideas. That 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 · Health scoring · QBR design · Renewal ownership · Churn reduction · Expansion strategy
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
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
Ask Olabisi
Senior CSM · Available for opportunities
Hi. I am Olabisi's AI assistant. Ask me anything about her background, experience, CS philosophy, or how she thinks about retention and customer success.