Head of Software (Product & Technology)

Role Overview

You will own the full software and digital product strategy — from customer-facing experiences to the critical infrastructure that powers a rapidly scaling IoT fleet. A significant part of what you own is invisible to end users and mission-critical: the broker infrastructure, device communication layers, billing systems, and hardware control software that thousands of homes and businesses depend on. At the same time, AI is changing the software world faster than we can process and the opportunities to experiment and drive more value through our software is sky-rocketing. Software plays a critical role end-to-end in our customer journey - from closing sales (and energizing communities with optimally designed grids) to unlocking long-term sustainability, project growth and success, and ultimately community impact. To date, we’ve just scratched the surface with what we can do with software.

Hardware and Software orgs jointly own product strategy, customer outcomes, and engineering culture — converging in a single roadmap where decisions cross boundaries (telemetry, OTA updates, comms protocols, billing flows, on-device intelligence). Within your team, software and product live in the same org intentionally - the people defining what to build and the people building it share accountability for outcomes. Software at Okra is not done when it ships - it's done when it's used, adopted, and driving the commercial outcomes it was designed for. Revenue enabled by Harvest insights, deployment time saved by Network Planner, support cost reduced by mobile LMA app - these are KPIs your products are held to.

Responsibilities

• Product Vision, Strategy & Roadmap - paint a picture for the longterm vision and define and prioritize the short term initiatives across our software stack (iot infrastructure, customer-facing tools, field-facing tools, internal tooling, and data) that will enable us to achieve this vision. Be able to communicate why we’re building what we’re building.

• Communication and collaboration - make and communicate tradeoffs and decisions to bring stakeholders along for the journey. Work closely with Head of Hardware to juggle dependencies, make tradeoffs, and set a clear plan for the entire engineering teams. Work with Head of Ops who owns internal software tooling. Work with software technical leads to cover the engineering expertise needed in your strategy.
  • External communication - pitch the business outcomes and product vision/roadmap in terms investors, grant-funders, and partners understand

• Customer and market insight - deep understanding of customers and their pains and the state of the competitive landscape. Know what problems are worth solving, find the hidden opportunities and gaps and bottlenecks. Search for ways to unlock more opportunities for last mile communities.

• Product culture and process - setting the product best-practices, from feedback to requirements,  experiments, success metrics, understanding of adoption/retention, and data analysis. Make sure we are not just a team that ships features, but one that delivers value and solves customer pains.

• Engineering culture, process and outcomes - accountable for setting a vision for how we do software engineering at Okra, standards for reliability, unit economics, deployments, incident management, and velocity. Know how to set minimum process to succeed at scale, while letting innovation thrive in the right places.

• Resource planning - translate software goals into resource requirements and build the team the company needs, to hit the goals. Recruit high performing product and engineers.

• Leadership - As a strategy team member, you represent the company internally and externally, people look up to you for clarity, advice, and support. You embody Okra’s culture and values and help carry it forward.

• AI strategy and execution — Okra has AI experiments today (Brainwave, conversational tools), uses AI in our dev process, and the boundary keeps moving. You own which AI capabilities become products vs. internal accelerants, set the eval and observability discipline for AI features in production, and balance latency, cost, and quality tradeoffs at scale.

• Go-to-market collaboration - working with sales, marketing, and customer success on feature launches, customer communications around changes, and how software updates get positioned

Technical Skills

• Software engineering across the stack - enough depth to earn trust and push back on decisions meaningfully. Be able to quickly learn about technical gaps as they arise.
• Understanding of IoT systems and device fleet management - MQTT or similar broker infrastructure, device provisioning, OTA updates, telemetry pipelines
• Understanding of cloud infrastructure, release management, security, and deployment practices
• Communication - translating between technical and non-technical, be able to inspire and align all different stakeholders
• Strategic prioritization - making clear decisions in the face of competing needs and constraints
• AI and data - existing experience, keen experimenter, and/or able to ramp up fast
  • AI tooling - continually learning about tool advancements and how they can contribute to how we build and what we build
  • Understanding of data and ML lifecycle (eval, observability, drift, feature stores)
  • AI product development (building AI features into the product)

Soft Skills

• Risk judgment - the ability to distinguish where speed is safe from where it is dangerous
• Cross-functional trust-building and stakeholder engagement
• Comfort working alongside a founder who has held this scope - you need to ramp up on a lot of context and need to earn the trust to extend it
• Coaching and technical mentorship - defining what growth looks like for software leaders and product managers

Required Experience

• 8+ years in software engineering or product, with at least 4 in a leadership role
• Experience with IoT, embedded connectivity, or other infrastructure where software directly controls physical systems — strongly preferred
• Strong enough technical foundation to earn the trust of senior engineers and engage meaningfully on architectural decisions
• Strong product foundation to build external relationships, understand the customer and market deeply
• Ability to work alongside a founder or executive who has held this scope previously

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