PRINCIPAL, TECHNOLOGY ENGINEERING

Director of Engineering
At Informed K12, we believe that operational excellence in school districts is one of the highest-leverage investments in public education. Our technology builds capacity for administrators and gives time and resources back to teachers by fixing one of the most overlooked problems in education: the slow, fragmented processes and workflows that carry a district's most critical work.
We are hiring a Director of Engineering who treats team design, the stack, and engineering strategy as one problem. A platform choice, a runtime, a service boundary — these are org decisions wearing technical clothes. We need someone who can hold a specific thesis about how this engineering org should work, then change the org and the stack together when the thesis is wrong.
This is not a people-management role with an engineering background. It is engineering leadership: the system you are designing is the organization and the platform it produces. In the age of AI, anyone can ship a feature in an afternoon. The scarce skill is keeping the system coherent as it grows — and building an org that compounds quality instead of accumulating entropy. You'll join an engineering org in investment mode. The next chapter depends less on adding headcount than on designing the teams, interfaces, and decision rights that let a small org compound — and on making the stack and platform choices that will shape those teams for years.
Own team design and ownership boundaries as engineering work — including how a stack or platform choice will reshape who talks to whom, what each team can hold in their heads, and what the architecture becomes
Own engineering strategy: which bets we make, which requirements we question or delete, and which work we refuse because it is proxy activity
Own the quality bar org-wide: maintainability, test discipline, minimalism, and the fight against entropy — not as a cleanup sprint, as how we ship
Own hiring bar, leveling, and growth paths — including the senior IC seats that define the next generation of the platform
Own partnership with Product, Customer Success, and company leadership as a peer — in the room with customers when it matters — synthesizing competing constraints into a clear engineering point of view
You have a specific thesis about how engineering orgs should work — not "we'll figure it out" — and you update the thesis when evidence says so. You delete processes, meetings, and work that do not serve the outcome.
You can walk through a platform or runtime decision and say what org it will produce — who owns what, what load it puts on people, what architecture it will calcify. You are not a scrum master with a bigger title.
You ship working software, not ceremony. 12+ years of engineering experience, including significant time leading multi-team orgs — not only managing a single squad

• Has made (or advised) a stack, platform, or runtime decision and can describe the org it produced — team boundaries, load, and architecture — including what they would reverse
• Can describe how they protected quality at org scale: maintainability, tests, entropy — not a one-team cleanup
• Has been close to customers in a leadership role and can say what that proximity changed about their engineering judgment
• Uses Cursor, Claude Code, Codex, or equivalent in real work and has a point of view on how AI changes engineering leadership — hiring, review, quality — not just IC speed

We want to see how your beliefs on engineering, product, and teams have evolved over time and how you put those beliefs into practice. We are not testing whether you've read a particular reading list. We are testing whether you've internalized the ideas and whether you can articulate where you disagree with them. If conversations about how team boundaries become system boundaries, what a platform choice does to an org, how environments destroy or protect deep work, shaping work before building it, one-way vs two-way door decisions, outcomes vs proxy metrics, conceptual integrity, entropy in long-lived systems, internal quality and test discipline, and AI-on-the-loop engineering are familiar territory, you'll feel at home in our process.
Every application is personally reviewed by a member of our team. Include the following in your application:

A 1-paragraph answer to: "Describe a platform, stack, or org-boundary decision you made (or inherited) that later shaped the team in ways you did not intend. A link to writing we can read (any format)
Optional: an opinion on a software book or thinker you consider overrated or underrated
Healthcare coverage: 100% for employees, 35% for dependents.
Monthly productivity allowance (co-working space, coffee shop, working lunch).
New hire stipend for remote office setup.
Monthly wifi reimbursement.
New hire home office supply stipend.
If you want to help school districts win, not just adopt software, we want to get to know you.