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William CainWC
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William Cain

@williamcain

Product management director at Trimble Transportation who improved TMW Suite retention from 89% to 96%.

United States
Message

At Trimble Transportation, I improved TMW Suite net revenue retention from 89% to 96% by restructuring portfolio investment and aligning funding to financial outcomes. I also reduced annual churn from 11% toward 7%.

I launched a mobile communications messaging platform and established the product and engineering team structure, delivery framework, and execution roadmap. I’m delivering a cloud-native replacement for a legacy TMS-to-driver messaging system.

Previously, I established a scalable Agile delivery framework for a 140-person Agile Release Train. By implementing test automation and standardizing JIRA-based workflows, I reduced manual regression testing effort by 67%.

As Director of Client Services & Customer Success, I restructured a $35M support organization around customer outcomes, improving gross customer retention from 94.5% to 98.6% and generating $1.5M in incremental recurring revenue.

Experience

Work history, roles, and key accomplishments

Trimble Transportation logoTT
Current

Director, TMS Product Management & Engineering (STO)

Jan 2022 - Present (4 years 10 months)

Delivered a fully cloud-native replacement of a legacy TMS-to-driver messaging system within 12 months, improving performance and customer retention. Launched a mobile communications messaging platform and established the full product and engineering team structure aligned to ICP requirements.

Trimble Transportation logoTT

Director of TMS Operations / Release Train Engineer / Agile Coach

Jan 2017 - Dec 2022 (5 years 11 months)

Established a scalable Agile delivery framework across Product, Engineering, QA, PS, and Customer Support for a 140-person ART, enabling consistent governance and release predictability. Reduced partner-related escalations by 40% and eliminated three recurring alignment forums through a Vendor Certification Program and formalized interface contracts.

Trimble Transportation logoTT

Senior Project Manager

Managed projects within Trimble Transportation, applying project management methodologies to deliver successful outcomes.

Trimble Transportation logoTT

Client Support Team Leader

Led a client support team, ensuring effective service delivery and team performance.

Education

Degrees, certifications, and relevant coursework

Kent State University logoKU

Kent State University

Bachelor of Business Administration, Business Administration

Bachelor of Business Administration degree from Kent State University.

Tech stack

Software and tools used professionally

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