2011 — 2015 · Salt Lake City
MasteryConnect
Senior Software Engineer → Team Lead
- Built assessment tools for K-12 teachers. Learned to ship.
- Went from writing the code to leading the team that wrote it.
1st inning
Career stats
Fifteen seasons. Four startups, one fintech giant, one bootcamp that changed a lot of lives. Here's the back of the card.
Holdaway · Career2011 — Today
2,000+
People into their first software jobLambda School
1,200
Bank & data partner integrationsPlaid
12→46
Engineers on one orgPlaid
$6MM
ARR from zero. Then acquired.Shopgenie
DAY 1
New-hire first commit, down from day 12Plaid
80%
Apprentices converted to full-timeLambda School
70%
Of Plaid's traffic moved to new integrationsPlaid
15
Seasons in the league2011 — today
2nd inning
The two thousand
From 2017 to 2021 I ran outcomes at Lambda School. I built Labs, our in-house apprenticeship. I ran pods of grads working real contracts for real companies. And I got to watch more than two thousand people get hired as software engineers for the first time.
“The most rewarding work I've ever done.”
Every dot is a person. Say hi.
3rd inning
The journey
2015 — 2017 · Lehi
Podium
Engineering Manager, Integrations
- Plugged Podium into the tools customers already lived in: Salesforce, DealerSocket, Eaglesoft, DispatchTrack and ~25 more.
- Elixir/Phoenix API clients, RabbitMQ between services, and one on-prem C# integration we don't talk about.
2017 — 2021 · San Francisco (remote)
Lambda School
VP of Outcomes
- Founded Labs, the in-house apprenticeship that turned students into working engineers.
- Ran pods of grads on real client contracts. 80% converted to full-time.
- Helped 2,000+ people land their first software job.
2021 — 2023 · Salt Lake City
Plaid
Sr. Engineering Manager, Data Access
- API/OAuth integrations with 1,200 banks and data partners. Moved 70% of Plaid's traffic onto them.
- Grew the org from 12 to 46 engineers and started an apprentice program for non-traditional backgrounds.
- Rebuilt onboarding: time to first code change went from 12 days to Day 1.
2023 — 2025 · Scottsdale
Shopgenie
Head of Engineering
- Built the engineering and product teams: 12 engineers, 2 PMs and a designer.
- Company went from $0 to $6MM ARR.
- Acquired by Tekmetric in late 2024.
2025 — Today
Yakai
Cofounder and CTO
- AI for brands that sell licensed goods: product submissions, approvals and royalty reports.
- We do the heavy lifting for your licensing. yakai.app
2026 — Today
Gauntlet
Instructor & Coach
- Coaching engineers through an intense, AI-first training program. Office hours, 1:1s, and game film on mock interviews.
- Getting the band back together. gauntletai.com
4th inning
Scouting report
Graded on the traditional 20–80 scale. 50 is big-league average. 80 is Pedroia turning two.
Player evaluation
Hiring12 → 46 at Plaid80
Developing talent2,000+ first jobs80
CultureTwo apprentice programs75
Shipping$0 → $6MM ARR75
Integrations~1,230 and counting70
GolfCareer earnings: $1640
BYU optimismHas been hurt before20
Plus-plus makeup. Builds teams, then builds apprenticeship programs to keep filling them. Bets on people other clubs pass on, and is usually right. Watches mock interviews like game film. Will book the tee time.
— Area scout
5th inning
From the press box
Selected dispatches from @Ryan_Holdaway.
Internet went down in the middle of a Zoom call. Walk out of my office to find that my 4 year old daughter had filled up a plastic tub with water and foaming soap to give her toys a bath. She was using the router as a boat.
Holdy@Ryan_HoldawayOne of the first hires at every software company should be a former K-12 Teacher that you put in charge of customer onboarding and help center.
Holdy@Ryan_HoldawayBe the friend that books the tee time, that sends the calendar invite, that picks a time and place for the catch up lunch. 🍻
Holdy@Ryan_Holdaway6th inning · Rain delay
Go grab a Dr Pepper. We'll be right back.
Seventh-inning stretch
Off the field
Red Sox
BYU
Jazz
Men's league
Orem, Utah
Silicon Slopes. Home office. Mountain time, all the time.
Girl dad ×3
Outnumbered 4 to 1 at home. Wouldn't trade it.
Red Sox lifer
Yankees skeptic, professionally.
$16 career earnings
Won it at men's league. Weighing the pro tour.
Bottom of the 9th
Let's play two.
Building a team, hiring a leader, or looking for someone to coach yours? Inbox is open.
ryan@rholdy.com