Director of Engineering

Location: Remote (US) | Travel: 5-10% | Reports to: VP of Product, Design, and Engineering Who We Are 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 have been expanding our impact since 2012, building the product depth, customer relationships, and operational track record required for this work. For engineering, this is a build phase: we are in investment mode, growing the team and giving senior engineers room to define how AI changes the way software gets built here. Much of K-12 software grows by acquisition and cost-cutting. We grow by building, and we are hiring the people who will do it. Why the Problem is Interesting Our engineering challenges aren't about scale. They're about domain depth and distilling complexity into elegant primitives that model how districts actually work. School districts are among the most process-dense institutions in the country: every workflow encodes board policy, bargaining agreements, and state law, and every district encodes them differently. The hard problem is finding the primitives underneath 100 apparently unique processes — deciding what's essential variance and what's cruft and unnecessary complexity, without breaking workflows where a mistake means someone doesn't get paid. If you find that kind of complexity more interesting than another distributed-systems problem, you'll like it here. Why This Role Exists We're hiring a Director of Engineering who treats team design, the stack, and engineering strategy as one problem. How teams are bounded is how systems get built. 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 not ceremony, velocity theater, or ticket flow. 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 own that: maintainability, test discipline, restraint, and the conditions that let people do deep work. 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. What You'll Do 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 how work gets shaped before it is built — small teams, clear bets, fixed time and honest scope, collaboration over handoffs — not estimate theater or ceremony Own the conditions for deep work: continuity, low interruption, and an environment that does not destroy teams through well-meaning process 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 Who You Are 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 question requirements before you staff them. You delete processes, meetings, and work that do not serve the outcome. You see team shape and the stack as the same design. 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 protect the conditions of good work. You know teams die from interruption, fragmented attention, and defensive bureaucracy — not from "bad culture." You design for continuity and deep work. You ship working software, not ceremony. You shape work before teams build it. You prefer small teams, honest scope, and collaboration over handoffs, estimates, and documentation nobody reads. You're well read in the ideas that shape this craft — teams, architecture, delivery — and you know exactly where you disagree. Your opinions come from production. You listen, synthesize divergent views, then assert a point of view and own it. What We Look For Required 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 Preferred Has published, talks or posts, not for the credential but as evidence of reflective practice Prior experience with regulated industries, K-12, or public-sector procurement How to Prepare We want to hear you reflect on your career and experiences. 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. How to Apply 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. What was your model at the time, and what would you do instead?" A link to writing we can read (any format) Optional: an opinion on a software book or thinker you consider overrated or underrated Benefits and Perks Healthcare coverage: 100% for employees, 35% for dependents. Uncapped PTO. 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. Skills development stipend (begins at 1-year anniversary). If you want to help school districts win, not just adopt software, we want to get to know you. Informed K12 is an equal-opportunity employer. We do not require degrees. We do require evidence. Compensation The base pay range for this role is $180,000 – $226,000 per year.