Rolake A

Senior Customer Success Leader with 13+ years of global experience in SaaS, FinTech, and Financial Services, managing multi-million-dollar enterprise portfolios across North America, EMEA, and APAC. Proven track record of driving customer adoption, retention, and ARR growth by building success plans, leading executive business reviews, and delivering measurable ROI. Skilled in Compliance Management, Customer Advocacy, Risk Management, and Account Monitoring with strong knowledge of SaaS business models, Data and AI analytics, and Customer Health Tracking.

Trusted advisor to senior stakeholders, with expertise in guiding global organizations to achieve business outcomes.

Senior Strategic Customer Success Manager at Assent (2024-08 – Present)

Manage a $3.5M enterprise portfolio, designing and executing success plans that align customer goals with measurable outcomes & compliance management requirements. Lead executive planning sessions and QBRs to showcase ROI, strengthen customer trust, and identify expansion opportunities.

• Manage a $3.5M enterprise portfolio, designing and executing success plans that align customer goals with measurable outcomes & compliance management requirements
• Lead executive planning sessions and QBRs to showcase ROI, strengthen customer trust, and identify expansion opportunities, significantly increasing adoption by 87%
• Partner cross-functionally with Sales, Product, Eng, Marketing and Support to deliver seamless program execution and value realization through strong internal collaboration
• Implement churn-reduction strategies that drove an 81% decrease in attrition and positioned accounts for long-term growth
• Own end-to-end renewal process, including forecasting, negotiation, and expansion planning to drive retention and revenue growth
• Leverage customer health analytics (NPS, adoption, usage data) to mitigate risks, improve engagement, and surface upsell opportunities
• Use Gainsight and Salesforce for account monitoring and health tracking, proactively mitigating churn risks and surfacing expansion opportunities contributing to 115% NRR

Senior Enterprise Customer Success Manager at Vidyard (2021-08 – 2024-07)

Owned a $2.5M+ book of business, delivering retention, adoption, and expansion to achieve a 5% revenue uplift. Spearheaded cross-functional projects including the launch of an AI-powered digital sales room platform that generated $890K in new revenue.

• Owned a $2.5M+ book of business, delivering retention, adoption, and expansion to achieve a 5% revenue uplift
• Spearheaded cross-functional projects—including the launch of an AI-powered digital sales room platform that generated $890K in new revenue in the first 4 months of launch
• Conducted training sessions with enterprise clients, translating VoC insights into product improvements and customer growth initiatives, increasing stickiness and adoption Y-O-Y
• Delivered QBRs/EBRs with enterprise clients to showcase ROI, ensuring retention through negotiation and compliance-aligned success planning with 79% increase in NPS
• Mentored and led a team of five CSMs, instilling best practices in adoption, success planning, and executive relationship management
• Monitored adoption and usage data for account health tracking, influencing expansion opps by 75%. Nurturing advocates and collecting success stories from power users

Customer Success Lead & Account Manager at Payactiv (2020-02 – 2021-08)

Designed and launched scalable CS programs, boosting client engagement by 91%. Introduced a streamlined onboarding program, accelerating TTV and client satisfaction. Oversaw 9 Customer Success Associates.

• Designed and launched scalable CS programs, boosting client engagement by 91%
• Introduced a streamlined onboarding program, accelerating TTV and client satisfaction
• Oversaw 9 Customer Success Associates, developing efficiency and retention strategies
• Partnered with Sales and Operations on renewals, forecasting, and negotiation to align SLAs and ensure long-term customer success - this partnership reduced churn by 79%

Account Manager & Client Success Advisor at Access Bank (2019-04 – 2019-11)

Drove 92% NPS and 95% retention by managing executive-level relationships and ensuring program objectives were consistently met.

• Drove 92% NPS and 95% retention by managing executive-level relationships and ensuring program objectives were consistently met
• Conducted customer business reviews, escalated needs internally, and secured measurable account growth

Customer Engagement Manager at Diamond Bank (2017-07 – 2019-03)

Optimized lifecycle engagement programs, reducing churn by 87% through proactive communication and issue resolution.

• Optimized lifecycle engagement programs, reducing churn by 87% through proactive communication and issue resolution
• Delivered regular program reviews, aligning account strategies with customer goals

Customer Relationship Manager at Diamond Bank (2011-06 – 2017-06)

Customer Relationship Manager role at Diamond Bank

MSc in Global Marketing – University of Liverpool (2016)