Jake A. Smith

Director of Engineering · Founder of CardPath

Seattle, WA me@jakeasmith.com Download PDF

Over two decades in software, nearly a decade of it building and leading the content platforms behind Yahoo and AOL through repeated M&A cycles and divestitures. Inside the AI transition from both sides: a year building agent tooling and the governance to trust it, two years advising enterprise leaders on adoption.

Experience

CardPath — Founder & Engineer

Jun 2025 – Present

Remote (Seattle, WA)

Founded CardPath, a dependency-first goal-management platform for cross-team dependencies; built the pre-launch product solo with AI coding agents, including a 35-tool MCP server behind self-hosted OAuth 2.1. Shipped under machine-enforced standards: blocking review gates, dispatch capped on human review time, per-call token telemetry. Now returning to engineering leadership.

Self-Employed — Engineering Leadership & Career Coach

Jul 2021 – Present

Remote (Seattle, WA)

Mentor engineering leaders through promotions, moves into management, restructuring, and post-M&A change; begun alongside the Yahoo directorship. The last two years have centered on AI adoption, and on human review as the new bottleneck: advising teams to ship the review agent with the codebase and run it before the PR lands.

Yahoo — Director of Engineering

Mar 2017 – Apr 2023

Remote (Seattle, WA)

Owned Yahoo's primary content platform — creation, curation, and syndication behind Yahoo Mail, Finance, Sports, Search, and the AOL and HuffPost brands — and from 2021 the push notification platform, serving 7B+ notifications a day. Ran roadmaps and OKRs jointly with a product partner on each team, leading engineers across PHP, Node, Java, and Scala.

  • Grew a globally distributed org from 7 engineers to 41 across four managers, consolidating five absorbed teams into four; a manager of managers from 2018. Held the org together through three M&A ownership changes by aligning opportunities with each person's career goals, and developed three engineers into first-time managers.
  • Created a unified cross-functional hiring team, adopted by peer organizations: one candidate pool, one leveling bar, candidates placed into their best-fit role anywhere in the org.
  • Co-established the working group that owned Yahoo's content schema and approved every change to it, standardizing years of inconsistent data and gating new properties as multiple platforms converged on one store.
  • Led the ~60-person, 13-week program replacing the content editor behind thousands of published pieces a day on five continents; as technical lead, read into the confidential divestiture driving the deadline. Zero outages at launch.
  • Absorbed the push notification platform and its team in 2021 and ran it through 2023; the team shipped SMS and VAPID-spec Web Push to 10M+ users, re-architected subscriptions on DynamoDB for 80% lower latency and ~$1.5M in annual savings, and replaced 75+ redundant editorial workflows with one push dashboard across News, Sports, Finance, AOL, and Mail.
  • Reduced Yahoo's primary CMS from dozens of significant outages a month to 3–4 minor incidents within a year of inheriting it — race conditions fixed, regression tests and retry logic added, failures given plain-language messages carrying traceable error codes — without pausing feature delivery, and directed its Ember-to-React rewrite via progressive cutover.
  • Led the teams that spearheaded Yahoo's company-wide request-tracing platform, and designed the content pipeline to degrade deliberately rather than fail: good-enough response, honest status, out-of-band retry, operator re-run.

AOL — Principal Software Engineer

Sep 2013 – Mar 2017

Remote (Orlando, FL)

Principal engineer on AOL's editorial platform infrastructure, including the publishing platform that served AOL.com, Engadget, and Autoblog live at over a billion page views a month.

  • Led the modernization of AOL's flagship publishing platform, which rendered the homepages of Engadget, Autoblog, and AOL.com and at peak ran 14 of the top 100 blogs on the open web: zero test coverage to 90%+, full CI/CD on Jenkins, and engineer onboarding cut from days of hand-rolled setup to minutes on reproducible Vagrant environments.
  • Designed an early distributed request-tracing system, propagating UUIDs through HTTP headers so a request could be followed across services, used for debugging and performance work across the public rendering infrastructure.
  • Architected SHIELD, a Node.js OAuth 2.0/OIDC identity platform that became the standard auth layer for editorial tooling; still in production more than a decade later.
  • Co-led the Contributor Network, the UGC platform that opened Engadget and other AOL brands to outside contributors: personally built the payments, payouts, analytics, and editorial review surfaces from scratch, and defined the security standards that made external publishing safe.
  • Owned DIMS, the on-demand image manipulation service behind nearly every image on AOL's properties.
  • Built the blue/green deployment suite behind zero-downtime on-prem-to-AWS migrations of all three.

Oklahoma Army National Guard — 11B Infantry

May 2008 – May 2014

Earlier

2004 – 2013
  • Senior Software Architect at VMR Products (Miami, FL), where an affiliate-payment rebuild with third-party fraud prevention cut costs 20%; software developer and lead systems administrator at Company52; earliest professional work at StillThinkingHQ from 2004, building sites and custom WordPress plugins for web publications.

Leadership & Skills

Leadership: Org design and scaling (7 to 41) · Manager of managers · Globally distributed teams · Hiring and talent development · Roadmap and OKR prioritization with product partners · Reliability: incident practice, blameless postmortems, runbooks · M&A integration and divestiture technical leadership

AI engineering: Claude agents, skills, and pipelines · MCP server design (OAuth 2.1, per-tool authorization, token-cost observability) · AI governance: machine-enforced standards, automated review gates · AI-adoption advisory for engineering teams

Platform: OAuth 2.0/OIDC identity federation · Graceful degradation · Distributed tracing and observability · Progressive cutover, blue/green, and zero-downtime AWS migrations · TypeScript, Node.js, React, PHP, Postgres, Redis