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Tim Chipperfield

Senior Engineering Manager, AI · Victoria, BC, Canada LinkedIn · Medium

Engineering leader who takes AI products from idea to production and helps whole engineering orgs adopt AI in ways that stick. Ruby on Rails engineer by background, with experience in edtech, fintech and payments.

Highlights

  • Led the team that built Thinker, Thinkific's AI teaching assistant, from concept to general availability. Learners using it complete courses at twice the rate of comparable learners who don't.
  • Led Thinkific's shift to AI-assisted development across R&D: after a false start with Copilot, rebuilt the rollout as an adoption program and reached 91% of merged code AI-generated within a year. Now moving teams to agentic workflows with Claude Code.
  • Built the quality and observability layer for a production AI system: self-hosted Langfuse tracing, an LLM-as-judge evaluation pipeline and weekly cohort analysis of real usage.
  • Helped scale a founding payments organization from 5 to 20+ engineers and launch a merchant payments product that now processes $70M+ per quarter.

Experience

Thinkific (online learning platform)

Senior Engineering Manager, AI · Feb 2025 – Present

  • Lead a senior team including a staff engineer; took Thinker from pilot through beta to GA with quality gates, staged rollouts and escalation paths.
  • Built and led a Power Users Guild, a peer champion network that carried AI adoption across teams I didn't manage.
  • Co-led an agentic delivery workflow, then rebuilt it into modular pieces when the heaviest users told us the orchestrated version was too slow.
  • Created the company's first AI strategy and co-founded its Vision Team; mentor engineering managers across the organization.

Engineering Manager · Dec 2021 – Feb 2025

  • Delivered the Public Graph API, a federated GraphQL platform for integrations and external developers.
  • Saved roughly $1.2M over two years through a new API gateway and vendor renegotiation.
  • Consolidated three teams into one during a reorganization and rebuilt delivery cadence.
  • Formed an early AI team whose foundations were reused across later AI products.

Engineering Team Lead, Payments · Apr 2021 – Dec 2021

  • Helped build the founding Payments organization and launched a merchant payments product in a regulated environment.

OrgMatch · Co-Founder & CTO · Jun 2021 – May 2024

AI-enabled ESG platform, built alongside Thinkific. Hired the founding team, built an AI-powered matching system across 40,000+ organizations, and turned a key adoption insight into a pivot and acquisition integration.

Earlier

  • Lendesk (software for mortgage brokers and lenders) · Software Development Team Lead · 2020–2021
  • PayWith (fintech) · Developer & Scrum Master · 2018–2020
  • Chipperfield Solutions · Founder & CTO · 2018–2020
  • TrueView (London) · Software Engineer & Scrum Master · 2016–2018

Before tech: international development and campaign work in Canada, Germany and Mozambique.

Speaking & Writing

  • Prompt Victoria AI Conference (2025)
  • PlatformCon (2024)
  • Writing on AI product development and adoption on Medium
  • Top 100 Innovators & Entrepreneurs (2025)

Education & Certifications

  • MA, Development Management, Ruhr-Universität Bochum
  • BA, Political Science, University of Victoria
  • Software Development, Makers Academy (London)
  • Certificate in Project Management, UBC
  • Professional Scrum Product Owner I, Professional Scrum Developer I, AWS Certified Cloud Practitioner

Outside work

🎸 Most of my free time goes to family and getting outdoors on Vancouver Island. I also try to stay active, play guitar (mostly for a very small, very enthusiastic audience at home) and keep up my languages (Portuguese, some German, Spanish, Hindi and French).

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