Director of Engineering

WIN Reality; Los Angeles (CA); On-site; USD 180,000 - 280,000; Full time

Job summary

WIN Reality, Inc. is seeking a Director of Engineering to lead the engineering organization and deliver the product roadmap for all WIN surfaces, including Smart Park camera systems, Blast Motion sensors, TrainVR, and web/mobile/backend platforms.

This is a hands-on leadership role focused on delivering high‑quality software and hardware integrations at scale. You will oversee seven direct reports across CV, AI, devices, backend, frontend, mobile, and Live Ops, shape the technical strategy, and

Qualifications

• 10+ years of software engineering experience, including 4+ years leading engineering teams and managing managers or tech leads.
• Track record shipping products that combine hardware and software — connected devices, cameras, or sensors.
• Hands-on depth in at least two of: computer vision, AI/ML, embedded/IoT, cloud backend, web, or mobile.
• Experience at modern, high-growth technology companies using a cloud-native stack.
• Based in, or willing to relocate to, Austin or Los Angeles.

Responsibilities

• Lead seven direct reports across computer vision, AI, connected devices, backend, frontend, mobile, and live operations.
• Hire and retain top engineering talent, and build a team known for ownership and craft.
• Set clear expectations, give direct feedback, and run performance management with rigor and care.
• Build an engineering culture rooted in accountability, technical excellence, and speed.
• Own execution of the product roadmap in partnership with Product and Design leadership.
• Translate roadmap priorities into staffed, sequenced, realistic plans — and deliver against them on the expected timelines.
• Surface risks, trade-offs, and slipped commitments early, with full context, so leadership can decide.
• Run a planning and delivery cadence (sprint, release, quarterly) that the rest of the company can rely on.
• Define and enforce the quality bar across device-connected and software products: testing, code review, release management, and observability.
• Ensure what ships works in the field — on thousands of deployed camera systems, on sensors in athletes’ hands, and in apps used every day.
• Own incident response, root-cause analysis, and the systems that prevent repeat failures.
• Partner with Live Ops to keep the deployed Smart Park fleet performant.
• Guide architecture decisions across connected devices, camera and sensor stacks, computer vision and AI pipelines, cloud backend, and web and mobile clients.
• Keep WIN’s stack modern: make sound build-vs-buy calls, manage technical debt deliberately, and adopt new tools where they make the team faster.
• Ensure our data infrastructure scales with growing device volume and new data products.
• Work hand in hand with the VP of Product and design leadership to shape what gets built and why.
• Partner with hardware leadership and Operations on firmware, device provisioning, and deployment.
• Manage external engineering partners and vendors where they extend the team’s capacity.
• Seven direct reports across WIN’s engineering disciplines.
• Close partners: VP of Product and the product team, design, hardware leadership, Smart Park operations, and Live Ops.
• This is a hands-on leadership role. The Director is expected to understand the code, the systems, and the devices well enough to make good calls and earn the team’s trust.

Skills

Software engineering

Engineering leadership

Hardware‑software product shipping

Cloud-native stack

CI/CD / modern practices

Job description

The Director of Engineering leads WIN’s engineering organization and owns delivery of the product roadmap — on time and at quality. This role spans every surface WIN ships: Smart Park camera systems, Blast Motion sensors, TrainVR, and the web, mobile, and backend platforms that turn that data into insights for players, coaches, teams, and facilities.

About WIN Reality, LLC

WIN Reality is changing how baseball and softball players across the world train to get better. Our team is full of world class developers changing the VR landscape, former professional ballplayers dedicated to improving the way the game is played, and people passionate about creating a one of a kind experience. We’re always looking for talented people to join our team, and to continue pushing the boundaries of what’s possible.

Description

Reports To: COO

About the Role

The Director of Engineering leads WIN’s engineering organization and owns delivery of the product roadmap — on time and at quality. This role spans every surface WIN ships: Smart Park camera systems, Blast Motion sensors, TrainVR, and the web, mobile, and backend platforms that turn that data into insights for players, coaches, teams, and facilities.

Our products cross hardware and software, B2B and consumer. A single feature might touch firmware on a connected device, a computer vision model running on camera footage, a cloud data pipeline, and a mobile app in a parent’s hand. You’ll lead the team that makes all of it work together.

This is a hands-on leadership role for someone who has built and shipped modern products at high-growth technology companies. Success is measured by what ships, when it ships, and how well it works in the field.

Key Responsibilities

• Lead, coach, and grow a team of seven direct reports spanning computer vision, AI, connected devices, backend, frontend, mobile, and live operations.
• Hire and retain top engineering talent, and build a team known for ownership and craft.
• Set clear expectations, give direct feedback, and run performance management with rigor and care.
• Build an engineering culture rooted in accountability, technical excellence, and speed.

Roadmap Delivery

• Own execution of the product roadmap in partnership with Product and Design leadership.
• Translate roadmap priorities into staffed, sequenced, realistic plans — and deliver against them on the expected timelines.
• Surface risks, trade-offs, and slipped commitments early, with full context, so leadership can decide.
• Run a planning and delivery cadence (sprint, release, quarterly) that the rest of the company can rely on.

Quality & Reliability

• Define and enforce the quality bar across device-connected and software products: testing, code review, release management, and observability.
• Ensure what ships works in the field — on thousands of deployed camera systems, on sensors in athletes’ hands, and in apps used every day.
• Own incident response, root-cause analysis, and the systems that prevent repeat failures.
• Partner with Live Ops to keep the deployed Smart Park fleet performant.

Architecture & Technical Strategy

• Guide architecture decisions across connected devices, camera and sensor stacks, computer vision and AI pipelines, cloud backend, and web and mobile clients.
• Keep WIN’s stack modern: make sound build-vs-buy calls, manage technical debt deliberately, and adopt new tools (including AI-assisted development) where they make the team faster.
• Ensure our data infrastructure scales with growing device volume and new data products.

Cross-Functional Partnership

• Work hand in hand with the VP of Product and design leadership to shape what gets built and why.
• Partner with hardware leadership and Operations on firmware, device provisioning, and deployment.
• Manage external engineering partners and vendors where they extend the team’s capacity.

Team & Structure

• Seven direct reports across WIN’s engineering disciplines.
• Close partners: VP of Product and the product team, design, hardware leadership, Smart Park operations, and Live Ops.
• This is a hands-on leadership role. The Director is expected to understand the code, the systems, and the devices well enough to make good calls and earn the team’s trust.

Who You Are

• You ship. You’ve repeatedly delivered complex products on committed timelines, and you know how to get a team there without burning it out.
• You’ve worked across the stack. You’re credible on connected devices and firmware, cameras and sensors, computer vision and AI, cloud infrastructure, and web and mobile — and you know how they fit together.
• You come from modern, high-growth engineering teams. You’ve worked with a current, cloud-native stack, CI/CD, and fast release cycles, and you bring those practices with you.
• You hold a high bar for quality. You don’t ship what you can’t stand behind. When something breaks in the field, you own it and fix the system behind it.
• You develop leaders. You’ve grown engineers into managers and tech leads, and your team trusts you.
• You tell the truth. You bring leadership the hard news — slipped dates, quality issues, your own mistakes — clearly and quickly.
• You care about athletes. You’re excited to build products that help players and coaches get better. A passion for baseball, softball, or sports is a plus.

How Success Is Measured

• Primary KPI: Roadmap commitments delivered on the expected timelines.
• Quality: Defect escape rate, incident frequency and severity, app ratings, and field reliability of deployed devices.
• Velocity: Cycle time and release cadence across surfaces.
• Team: Retention, hiring against plan, and engagement of the engineering team.
• Platform health: Uptime, performance, and steady reduction of technical debt.

Qualifications

Required

• 10+ years of software engineering experience, including 4+ years leading engineering teams and managing managers or tech leads.
• Track record shipping products that combine hardware and software — connected devices, cameras, or sensors.
• Hands‑on depth in at least two of: computer vision, AI/ML, embedded and IoT systems, cloud backend, web, or mobile — with working fluency across the rest.
• Experience building both B2B and consumer products.
• Experience at modern, high-growth technology companies using a cloud‑native stack and current engineering practices.
• Proven ability to deliver a roadmap on committed timelines at a high quality bar.
• Based in, or willing to relocate to, Austin or Los Angeles.

Preferred

• Experience with camera-based systems, computer vision in production, or sensor data pipelines.
• Experience operating a large fleet of deployed devices.
• Background in sports technology, sports data, or fitness and wearables.
• Experience scaling engineering across multiple product lines.