Chief Technology Officer

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
• 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