Director of Technology

Ocra is building the commercial developer platform for parking. The connective layer between sellers, booking channels, and the systems that move money between them. On top of it we ship SaaS: Ocra Direct, a white-label channel operators own; Ocra Terminal, where revenue teams price their entire portfolio from one surface; and Ocra Settlement, which reconciles what every channel owes. Each stands alone. Together they close the loop.

What separates Ocra is the machine learning. The platform sits where demand, pricing decisions, and realized revenue all pass through. A vantage point no incumbent has. That position lets our models learn what actually drives revenue in a market rather than mimic last year's rate sheet. Everyone else sells dashboards. We sell a system that gets better every day it runs.

We’re looking for a leader who is energized by working in a small, distributed team where autonomy, curiosity, and adaptability matter more than rigid processes (but we do work on our processes

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What you will be doing

• Own delivery across product, engineering, and QA
• : roughly ten people total. You're accountable for what ships, how often, and whether it holds up in production.
• Stay close to the work
• . At this size you're in design reviews, reading PRs, and occasionally in the code. You're not just a layer of management: you're the person who knows how the system actually works.
• Run the engineering system, not the engineers' tasks: Unblock dependencies, kill ambiguity early, and keep the path from "decided" to "in production" short and boring.
• Make reliability a property of the platform, not a heroic act
• : Uptime, error budgets, and an on-call rotation a small team can actually sustain.
• Scale the platform behind the pricing business
• : high-volume ingestion, event pipelines, and APIs serving hundreds of locations across a dozen booking channels, with more of both coming.
• Own the API surface as a product: Partner integrations, access-control systems, third-party channels, and our own applications all consume it. Versioning, contracts, deprecation, and docs are yours.
• Turn integrations into a repeatable pattern: Every new channel and every access-control vendor should be cheaper than the last. Today they aren't.
• Bring engineering rigor without ceremony
• : CI/CD, environments, testing strategy, and observability that speed a small team up rather than gate it. Process that costs more than it returns is your problem to remove.
• Partner with the AI team on the surfaces they depend on : data capture, event ingestion, model serving. You're not building models; you're making sure the platform they run on is dependable and instrumented.
• Sequence the roadmap honestly
• : surface tradeoffs early and say no clearly when something can't be done well in the time available.
• Hire deliberately: Going from where we are to ~10 means every hire is visible in the team's output. Set the bar, run the loop, and grow the people already here.
• Core skills & experience
• 8+ years building production software, with 3+ leading teams
• : Team sizes in the 5–15 range are exactly right; we're not looking for large-org management experience.
• Still technical and glad to be: You've led while remaining hands-on, and you'd be uncomfortable managing a system you couldn't debug.
• Depth in distributed systems and API platforms
• : services, queues and event streams, integration patterns, and data models that survive contact with the real world.
• A real SRE track record
• : SLOs, incident command, capacity planning, cost-aware infrastructure. You've woken up and fixed the class of problem rather than the instance.
• Experience scaling a system: Traffic, data, or integrations, and the scars to say what you'd do differently.
• Third-party integration experience
• : especially where partners are inconsistent, poorly documented, or occasionally wrong. Parking, travel, hospitality, payments, logistics, or marketplace backgrounds all translate.
• Ownership of QA strategy: what gets automated, what stays manual, and how quality gets measured rather than asserted.
• Clear written communication: Design docs, incident writeups, and roadmap updates people outside engineering actually read.
• Bonus points (wouldn’t it be sweet if …)
• IoT, hardware, or sensor integrations revenue systems, marketplaces, or financial reconciliation having taken a partner-facing API program from early stage to mature having been the first or second engineering leader somewhere
• Who you are
• Clear & Direct Communicator
• Communicates with clarity, precision, and honesty.
• Assumes good intent and avoids unnecessary fluff.
• Adaptable Generalist
• Curious and eager to learn unfamiliar parts of the system.
• Collaborative & Feedback-Friendly
• Pragmatic & Impact-Oriented
• Focuses on delivering value, not chasing perfection.
• Makes thoughtful tradeoffs between speed and quality.
• Flexible & Proactive
• Raises issues early and steps outside their lane when needed.
• Non-negotiables
• We value humility, curiosity, and outcomes over ego or rigid process.