Jake A. Smith

Director of Engineering · Founder of CardPath

Seattle, WA me@jakeasmith.com

Engineering leader for content platforms and the high-traffic products built on them. Six years leading engineering on Yahoo's content platform, as a manager of managers from 2018; before that, principal engineer at AOL on its flagship publishing platform. Inside the AI transition from both sides: a year building agent tooling and the governance to trust it, two years advising leaders on adoption.

Experience

CardPath — Head of Engineering

Jun 2025 – Present

Remote (Seattle, WA)

Took CardPath, a goal-management platform, from concept to a released product, using AI coding agents to drive implementation. Personally built a code factory that took well-written product descriptions from the backlog to pull requests ready for review, with open work capped at 45 minutes of estimated human review time.

  • Set the bar every coding agent built against, from layering and authorization to schema migrations, and turned each bug that slipped through into a new rule or an automated check.
  • Built an MCP server for CardPath and secured it with OAuth 2.1 and per-tool permission checks, so each AI agent could act only within its user's permissions.

Self-Employed — Engineering Leadership & Career Coach

Jul 2021 – Present

Remote (Seattle, WA)

Coach engineering leaders through IC-to-manager moves, managing underperformers, delivering bad news, and managing up to hit business goals. Also advise them on AI adoption, from outcome-first specs to a review agent shipped with the codebase, resulting in more effective teams and higher code quality.

Yahoo — Director of Engineering

Mar 2017 – Apr 2023

Remote (Seattle, WA)

Owned Yahoo's primary content platform, effectively a headless CMS behind Yahoo Finance, Sports, Search, AOL, and HuffPost, used daily by thousands of editors and contributors. From 2021, also managed the team running the push notification platform, which served 7B+ notifications a day.

  • Grew the org from 7 engineers to 41 across four managers, held it together through multiple M&A ownership changes, and developed three engineers into first-time managers.
  • Made the case to VPs and the CTO for the roadmap, resourcing, and funding, and took Yahoo's GM through the tradeoffs between competing platforms.
  • When HuffPost was sold, made the call to rebuild its content editor inside Yahoo's CMS; led a ~60-person extended team with product, design, and editorial to ship it in 13 weeks with zero downtime, zero bugs at launch, and no revenue impact.
  • Cut an inherited CMS from dozens of revenue-impacting incidents a month to three or four minor incidents within a year, without pausing the roadmap.
  • After the AOL–Yahoo merger, consolidated dozens of overlapping systems into one platform and moved AOL's brands onto it one at a time over two years.
  • Directed an 18-month rebuild of three ingest paths and 40+ microservices into one multi-region AWS engine: 2x faster, with bug mitigation typically cut from hours to minutes.
  • Ran the platform as a product for a few dozen internal verticals, with API and data contracts set early so teams built in parallel.
  • Replaced per-team interviewing with one shared interview team and leveling bar, then took the model to peer organizations.

AOL — Principal Software Engineer

Sep 2013 – Mar 2017

Remote (Orlando, FL)

Principal engineer on a publishing platform hundreds of engineers built on, which rendered AOL.com, Engadget, and Autoblog live at over a billion page views a month.

  • From July 2016, led the platform's team as its architect: set the technical direction and defined what the team worked on.
  • Led the modernization of the platform, which at peak ran 14 of the top 100 blogs on the open web: test coverage from zero to 90%+, full CI/CD, and engineering onboarding cut from days to minutes.
  • Architected SHIELD, a Node.js OAuth 2.0/OIDC platform that became the standard auth layer for editorial tooling; still in production more than a decade later.
  • Built the blue/green deployment tooling (pre-warming, scaling, fast rollback) that moved AOL.com, Engadget, and Autoblog from on-prem to AWS with zero downtime.
  • Built the payments, payouts, analytics, and editorial review tools for AOL's Contributor Network, which opened Engadget and other brands to outside contributors, and set its security standards.

Oklahoma Army National Guard — 11B Infantry

May 2008 – May 2014

Earlier experience

2004 – 2013
  • Senior Software Architect at VMR Products
  • Software developer and lead systems administrator at Company52
  • Custom CMSs for web publications at StillThinkingHQ

Leadership & Skills

Leadership: Manager of engineering managers · Org design and scaling (7 to 41) · Developing engineers into first-time managers · Framing technical tradeoffs for executives · Roadmap, scope, and delivery commitments with product, design, and editorial partners · Hiring: shared interview teams and one leveling bar · Reliability: incident-response standards (time to first response, time to root cause), blameless postmortems with tracked follow-ups, runbooks · Vendor and build-vs-buy evaluation · M&A integration and divestiture technical leadership

Platform: Content management systems (CMS), editorial and internal tools · High-traffic publishing platforms · API and data contract design · Content ingestion and syndication (Apple News, RSS) · Platform consolidation in continuous production · OAuth 2.0/OIDC identity · Notifications at scale · Distributed request tracing and observability · Progressive cutover, blue/green, and zero-downtime AWS migrations

AI engineering: Building with coding agents (Claude Code), skills, and subagents · Automated review gates and machine-enforced standards · MCP server design (OAuth 2.1, per-tool authorization) · AI-adoption advisory for engineering teams

Stack: TypeScript, Node.js, React, PHP, Postgres, Redis, AWS

Open source: Published http_build_url, a one-function PHP polyfill that reached ~20M installs; deprecated it once PHP shipped the feature natively.