Job Title: Director of Engineering Department: Technology/Engineering Location: Remote/Hybrid - Vancouver preferred Reports to: CEO Position Type: Permanent, Full-time Stage: Growth-Stage SaaS Company Industry: Creator Economy / Digital Media / Content Monetization

About Us

The Coaches Site is an education and social platform that enables coaches of all sports to create, save, organize and share coaching content. Offering solutions for individuals and sports organizations, The Coaches Site helps coaches explore new resources, connect with a global network of leaders and build their digital development playbook.

We are building the operating system for content creators—a platform that enables sports coaches and organizations to distribute, engage their audiences, and monetize their content through subscriptions and digital courses. Our mission is to ensure every kid has access to a great coach, and we accomplish this by democratizing coach education.

As we enter our next phase of growth, we are looking for a Director of Engineering who can lead our small but growing engineering team, and scale our platform, team, and technology while helping shape the future of the creator economy in the sports industry.

Our core platform runs on a trusted LAMP stack (PHP, MySQL, Apache) containerized with Docker and managed via GitHub.

Role Overview

The Director of Engineering is a senior executive responsible for technology vision, architecture, engineering execution, and product delivery. This leader will partner closely with the CEO and leadership team to ensure the company has the technical foundation required to scale revenue, accelerate innovation, and deliver exceptional customer experiences. Additionally, this person will be responsible for leading and scaling the engineering team alongside the business.

This is a hands-on role — the Director of Engineering will be expected to engage directly with the codebase, make architectural decisions, and work alongside engineers day-to-day, not just manage from above. At the same time, this is a leadership team role with meaningful strategic responsibility, not purely an execution position. As the company grows, this role has a clear path to expand: the right candidate may grow into a formal Chief Technology Officer.

This role requires a rare combination of strategic leadership, engineering excellence, organizational development, and a deep appreciation for creator-focused businesses. The ideal candidate has successfully led engineering teams through rapid growth and understands the challenges of scaling SaaS platforms, content delivery systems, subscriptions, payments, and AI-enabled experiences..

Key Responsibilities

Technology Strategy & Vision Develop and execute the company's long-term technology roadmap aligned with business objectives. Evaluate emerging technologies and AI capabilities that can create competitive advantages. Drive architectural decisions that support scalability, reliability, security, and speed of innovation. Serve as a strategic thought partner to the CEO and executive team.

Engineering Leadership Lead and scale engineering, infrastructure, and data teams. Build a high-performance engineering culture centered on ownership, accountability, and continuous improvement. Recruit, mentor, and retain exceptional technical talent. Establish clear processes for planning, prioritization, and delivery.

Platform Architecture & Scalability Ensure the platform is highly available, secure, and performant. Design systems capable of supporting millions of users and creators. Optimize content delivery, streaming, APIs, search, recommendation systems, and data infrastructure. Drive observability, reliability, and operational excellence.

Product & Customer Experience Partner with Product and Design leaders to deliver features that create customer value. Champion user experience, performance, and product quality. Balance technical debt, innovation, and speed to market. Foster close collaboration between engineering and go-to-market teams.

AI and Innovation Identify opportunities to leverage AI across content discovery, personalization, search, workflow automation, and creator productivity. Build internal capabilities for experimentation and rapid deployment of AI features. Evaluate buy-versus-build decisions for AI infrastructure and services.

Security & Compliance Own cybersecurity strategy and risk management. Ensure platform reliability and data privacy. Lead compliance initiatives including SOC 2 and other relevant frameworks. Establish disaster recovery and business continuity practices.

Data & Analytics Build scalable data infrastructure and analytics capabilities. Enable product insights and experimentation through metrics and dashboards. Support recommendation engines, personalization, and creator intelligence capabilities.

Business Partnership Collaborate with Sales, Marketing, Customer Success, and Finance to align technical priorities with business goals. Support due diligence processes with investors, partners, and customers. Translate technical concepts into clear business outcomes for stakeholders and the Board.

What Success Looks Like

First 90 Days Build relationships across the organization. Assess platform architecture and engineering processes. Identify key technical risks and scaling opportunities. Establish engineering metrics and operating cadence.

First Year Improve development velocity and platform reliability. Scale engineering capabilities to support rapid growth. Deliver strategic product initiatives and AI capabilities. Strengthen security and operational maturity. Build a world-class engineering culture.

Long-Term Create a technology platform capable of supporting significant scale. Enable new monetization opportunities for creators. Position the company as a category leader in the creator economy. Build an organization that attracts and retains elite technical talent.

Qualifications

Required 10+ years of software engineering experience, including 5+ years in senior engineering leadership roles. Experience leading teams through growth-stage SaaS environments. Deep expertise in cloud architecture, APIs, distributed systems, and modern software development practices. Proven ability to scale engineering teams and processes. Experience managing technical budgets and vendor relationships. Strong communication skills and executive presence. Demonstrated ability to translate business strategy into technical execution.

Preferred Experience in creator platforms, marketplaces, media, streaming, education, or subscription businesses. Background with payments, subscriptions, community platforms, and digital commerce. Experience with recommendation engines, search, and AI/ML systems. Familiarity with SOC 2, GDPR, and modern security frameworks. Previous experience participating in fundraising, board presentations, or M&A diligence. It would be preferred if the candidate were located in Vancouver or in close proximity.

Leadership Competencies Builder - Thrives in ambiguity and creates scalable systems, teams, and processes. Product Thinker - Understands that technology exists to create customer and business value. Talent Magnet - Attracts, develops, and empowers exceptional people. Operator - Balances speed, quality, and execution with pragmatism. Strategic Partner - Collaborates effectively across functions and communicates clearly with executives, investors, and boards. Customer Obsessed - Deeply understands creators and continually seeks to improve their experience.

Why Join?

This is a rare opportunity to lead technology at a pivotal stage of growth — and in the process, help define an entirely new category. You'll shape how creators in the sports industry distribute and monetize their IP, while building a world-class engineering organization and platform capable of serving millions of users worldwide.

But beyond the scope of the role, you'll be joining a group of people at The Coaches Site who are deeply invested in what they're building — where your decisions matter, your voice carries weight, and the work you do has a direct, visible impact on the company and the creators we serve.

What gets built here will be felt on fields, courts, and training facilities around the world. These windows don't open often — a chance to be the technical architect of a category-defining company at the moment it's taking off!

Compensation

Range: $120,000-$150,000 Meaningful equity participation Performance bonus Health and wellness benefits Flexible remote work environment Opportunity to shape a category-defining company

Application Instructions

To apply, please submit your resume and a brief cover letter to jamie.henry@thecoachessite.com with the subject line Director of Engineering – [Your Name] by July 10, 2026. Applications will be reviewed on a rolling basis, and the position will remain open until filled. Only candidates selected for an interview will be contacted.

Equal Opportunity Statement

The Coaches Site is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, national origin, age, disability, veteran status, sexual orientation, gender identity, or any other characteristic protected by applicable law. We are committed to building a diverse and inclusive workplace where everyone feels valued and supported.