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Ryan Boyle

@ryanboyle

Strategic Customer Success Manager at SchoolAI who protected a 9,700+ teacher deployment and delivered 95% gross revenue retention.

United States
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At SchoolAI, I managed an $1.2M ARR portfolio of 80+ accounts across the U.S. and 20+ countries. I led renewal strategy for $538K across 12 enterprise and strategic agreements, delivering 95% gross revenue retention in H1 2026.

I protected a 9,700+ teacher deployment by analyzing usage, identifying adoption champions, and grounding the executive renewal case in engagement and value. I also partnered with Product and Engineering to resolve critical LMS and integration issues.

At Workstream, I managed the company's largest enterprise customer, valued at $2.4M ARR, and delivered 106% net revenue retention in 2024 in a mid-market role. Earlier, I helped establish Workstream's first customer onboarding function and created repeatable playbooks, training resources, and implementation processes.

Experience

Work history, roles, and key accomplishments

SC

Senior Strategic Customer Success Manager

SchoolAI

Apr 2025 - Jul 2026 (1 year 3 months)

Owned a $1.2M ARR portfolio of 80+ accounts across multiple U.S. states and 20+ countries, balancing executive strategy, adoption, risk management, and responsive customer support. Led renewal strategy for $538K across 12 enterprise and strategic agreements and delivered 95% gross revenue retention in H1 2026.

WO

Strategic Customer Success Manager

Workstream

Oct 2024 - Apr 2025 (6 months)

Led executive relationships, retention strategy, and long-term success planning for the company's largest enterprise customer, valued at $2.4M ARR. Managed 30 additional upper-mid-market and enterprise customers representing $1.8M ARR, for a total strategic portfolio of $4.2M ARR.

WO

Senior Client Onboarding and Implementation Manager

Workstream

Mar 2021 - Jun 2022 (1 year 3 months)

Helped establish the company's first customer onboarding function and created repeatable playbooks, training resources, and implementation processes adopted by the team. Led concurrent implementations from discovery through configuration, launch, and adoption, achieving an 85% customer usage rate—the highest on the team.

Education

Degrees, certifications, and relevant coursework

Brigham Young University–Idaho logoBU

Brigham Young University–Idaho

Bachelor of Science, Business Management

Bachelor of Science in Business Management with a focus on Marketing from Brigham Young University–Idaho, completed in 2015.

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