Chief Technology Officer

Chief Technology Officer
Chicago – Hybrid

Reports to Chief Executive Officer

Big Blue Swim School is a fast-growing franchise system that aims to show kids they can do anything by unlocking their full potential in the water. With 55 open locations providing children’s swim lessons across the US, plus more than 250 additional franchise locations sold, Big Blue locations run on our proprietary software platform for enrollment, billing, scheduling, and staff management. This platform is central to how every location operates, and its reliability and evolution are directly tied to the health of our franchise relationships.

We are seeking a Chief Technology Officer who can mature our engineering practices, build trust with a franchise network, and strengthen the technical foundation for sustainable, disciplined, and differentiated growth. This is a hands-on leadership role: the right candidate is energized by close-to-the-work engineering leadership and experienced building rigorous process in a high-growth environment.  

Key Responsibilities:

• Provide strategic and operational leadership for all technology functions, including oversight of proprietary software system, cybersecurity programs, and third-party vendor management ensuring secure, reliable, and scalable technology performance aligned with organizational objectives
• Partner with senior leadership to translate business and franchise priorities into a disciplined, clearly sequenced engineering roadmap
• Lead and develop a lean, cross-functional development and analytics team, operating hands-on and close to the work rather than through management layers
• Serve as the primary technical voice in franchisee-facing communications and forums including incident response, roadmap transparency, and periodic business reviews building trust through accountability and consistent follow-through.
• Own build vs buy vs integrate strategy that protects team focus and platform coherence
• Establish and enforce engineering standards: release management, QA process, code review, incident response, and post-mortems
• Partner closely with the Chief Architect, who holds deep institutional knowledge of the proprietary platform and its architecture, to ensure new investments are built on a sound technical foundation.
• Improve engineering capacity and process maturity: sprint discipline, backlog health, delivery predictability, AI adoption, and a culture of accountability
• Build a proactive controls and monitoring culture that reduces the frequency and severity of platform incidents before they reach operators or customers
• Assess current technical debt and infrastructure limitations and develop a sequenced remediation plan that improves the platform without destabilizing ongoing operations
• Establish and maintain engineering documentation standards as a foundational organizational capability

Qualifications:

• 10+ years in software engineering or technical leadership, with at least 4 years in an executive leadership role at a SaaS company – ideally in a high-growth, resource-constrained, or scale-up environment
• Demonstrated experience inheriting an existing platform and engineering team: stabilizing, improving, and scaling without unnecessary rebuilds; comfort with legacy codebases and complexity is essential
• Background in SaaS platforms, ideally in B2B, multi-tenant, or franchise/multi-unit environments where reliability is operationally critical
• Experience with subscription billing, recurring revenue systems, or payment processing infrastructure
• Strong command of SaaS infrastructure, release engineering, QA processes, and incident response frameworks
• Track record of building engineering process maturity in organizations
• Deeply technical and willing to be hands-on, including ability to review architecture decisions, evaluate code quality, diagnose system issues, and earn the trust of the engineering team from day one
• Active user of AI-assisted engineering tools with a demonstrated ability to embed these into team workflow and multiply a small team’s output
• Experience designing or overseeing AI/ML architecture on top of operational SaaS data with a practical understanding of how to move from raw transactional data to actionable intelligence
• Able to communicate technical realities, timelines, and tradeoffs to a non-technical audience of franchisees, operators, and executives
• Cross-functional collaborator: effective partner to Operations, Finance, Franchise Development, and Marketing

We Offer:

• Hybrid flexibility with a collaborative home base in the Chicago area
• The opportunity to shape an engineering function in a growing franchise system
• Comprehensive health benefits with a substantial employer premium contribution
• Competitive paid time off
• 401k with company match
• Competitive total compensation package including performance bonus. The expected salary range for this position is $225,000–$275,000. Final compensation will be determined based on experience, qualifications, and business needs

Big Blue Swim School follows an equal opportunity employment policy to all employees and applicants for employment without regard to race, color, religion, national origin, sex, gender identity, age, physical or mental ability, sexual orientation, marital status, veteran status, and genetic information. If you require reasonable accommodation during the application or hiring process due to a disability, please contact us at [email protected].