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Jermaine Grant

@jermainegrant1

Operations leader who improved service delivery across SaaS, healthcare, and travel assistance, including 99% revenue retention at Terra Dotta.

Ghana

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What I'm looking for

Remote contract or full-time opportunities where I can apply senior operations expertise to process improvement, service delivery, workforce/capacity planning and operational analysis. Particularly interested in AI training/evaluation roles where real-world operations, healthcare or service-delivery expertise can improve AI reasoning and outputs.

At Terra Dotta, I led customer success operations for a global education and travel-risk SaaS platform. I managed a $20M annual renewal portfolio and achieved 99% revenue retention during company-wide restructuring.

At World Travel Protection (Zurich Insurance Group), I led operational and digital-transformation leaders supporting medical assistance, security, traveler support technology, and client service delivery. I also led business and service-operations restructuring, contract renegotiation, and process changes to improve cash flow and operating performance.

Across SaaS organizations including TransLoc, DreamBox Learning, Formative, and Element451, I built Customer Success, Customer Support, and Professional Services functions totaling 30 employees and managing more than $10M in annual recurring revenue. Focused resourcing and process improvements reduced time-to-value by more than 40%.

Earlier, at TriWest Healthcare Alliance, I directed operations across healthcare service centers and VA clinic teams, achieving $2.3M in G&A savings while meeting appointment service-level requirements with 30% fewer staff. My work across International SOS / MedAire / TRICARE Overseas and NHS Direct included 24/7/365 medical assistance, patient support, and public healthcare operations.

Experience

Work history, roles, and key accomplishments

Vice President of Customer Success

Terra Dotta

Mar 2025 - Dec 2025 (9 months)

Led customer success operations for a global education and travel-risk SaaS platform, managing a $20M annual renewal portfolio and achieving 99% revenue retention. Developed customer journey mapping and product-feedback frameworks to improve prioritization and customer outcomes.

EVP of Operations, North America

World Travel Protection (Zurich Insurance Group)

Apr 2023 - Mar 2025 (1 year 11 months)

Led operational and digital-transformation leaders supporting medical assistance, security, and traveler support technology. Managed restructuring, contract renegotiation, and process changes to improve cash flow and operating performance.

VP Customer Success & Operations

Various Software Startups

Mar 2018 - Apr 2023 (5 years 1 month)

Led customer success, support, implementation, and professional-services functions across SaaS organizations including TransLoc, DreamBox Learning, Formative, and Element451. Built teams totaling 30 employees and managed $10M in annual recurring revenue, improving retention by over 10% year over year.

Director of Operations

TriWest Healthcare Alliance

Aug 2015 - Mar 2018 (2 years 7 months)

Directed 400+ employees across a multi-channel healthcare operation. Achieved $2.3M in G&A savings while meeting SLAs with 30% fewer staff through productivity gains. Launched four service centers averaging 280 seats, developed criteria to convert 3,000 temporary staff to permanent employees, and implemented a 500-person virtual operation generating $1.5M in startup savings.

Head of Global Operations

International SOS / MedAire / TRICARE Overseas

Dec 2005 - Dec 2015 (10 years)

Led complex 24/7/365 medical, security and travel-assistance operations with a 110-person cross-functional team. Managed workforce planning, process improvement, quality, P&L and crisis operations. Rebuilt the TRICARE Overseas staffing model within four weeks when volumes were 500% above forecast, supporting operational recovery and SLA performance.

Operations Manager

NHS Direct

Dec 2001 - Dec 2006 (5 years)

Promoted from Supervisor to lead daily operations and service delivery across multiple 24/7/365 nurse-led contact centers with more than 100 employees serving the London population. Managed frontline staff and service delivery in a high-volume public healthcare environment.