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Reagan Sterner

@reagansterner

I build compliant product documentation and knowledge bases that customers love.

United States
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What I'm looking for

I’m looking for a role where I can own product documentation and knowledge base strategy end-to-end—partnering with engineering, product, and design—while ensuring compliance, measurable impact, and a consistent customer-focused voice.

I’m a CSM and content-focused project manager who creates and scales documentation that helps customers onboard, understand analytics, and find answers fast. Across roles spanning content operations, technical writing, and project management, I’ve led end-to-end work—building templates and strategies, setting peer review processes with cross-functional teams, and verifying documentation alignment with regulatory and compliance standards, including HIPPA and SOC2.

I’ve driven measurable outcomes by modernizing knowledge bases and documentation workflows—streamlining publishing with a content management system, improving search and accessibility, and collaborating with engineers, product managers, and designers to keep everything accurate. Highlights include orchestrating a knowledge base revamp with new branding and advanced search that resulted in a 600% increase in article views, and managing article performance that contributed to a 20% increase in article traffic.

Experience

Work history, roles, and key accomplishments

Wintrust logoWI

Technical Writer

Jan 2023 - Jan 2023 (0 months)

Develop and maintain structured, scalable instruction manuals for mortgage software onboarding and ongoing maintenance. Conduct subject matter expert interviews to keep instructional material accurate and up to date.

Grin Technologies logoGT

Project Manager, UX

Grin Technologies

Jan 2022 - Jan 2023 (1 year)

Led migration and revamp of the company knowledge base by adding branding elements and advanced search capabilities, increasing article views by 600%. Streamlined documentation workflows with a content management system and improved documentation processes including API documentation and AI-assisted customer replies.

Apple, Inc. logoAI

Site Support Engineer & Writer, iCloud

Jan 2010 - Jan 2022 (12 years)

Managed call center escalations and delivered virtual training for front line agents, supporting issue reporting and process integrity. Tracked article performance to optimize content effectiveness and supported adoption through internal documentation and support-ready training.

Education

Degrees, certifications, and relevant coursework

Scrum Alliance logoSA

Scrum Alliance

Certified Scrum Master, Scrum

Earned the Certified Scrum Master certification (CSM) from Scrum Alliance (Certification #1771841).

TH

Technical Writer HQ

Technical Writer Certification, Technical Writing

Completed the Technical Writer certification program from Technical Writer HQ.

Baylor University logoBU

Baylor University

Bachelor of Science, Biology

Earned a Bachelor of Science in Biology from Baylor University in 2006.

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