Chief Technology Officer

About Connect Pay

Connect Pay provides comprehensive payroll, finance, and HR solutions specifically designed for small and medium-sized businesses and their employees. Our mission is constantly simplifying the state, federal, and local payroll processes while ensuring full compliance with every endpoint. Our focus on America’s SMB with fewer than one hundred employees creates a trust and efficiency equation driving high customer retention and growth.

At Connect Pay, we pride ourselves on combining modern technology with a personalized, human-first approach. We understand that every business is unique, so we design technologies to amplify our service layer, not eliminate it.

The Chief Technology Officer (CTO) is responsible for defining and executing Connect Pay's technology vision, strategy, and roadmap to support the company's long-term growth, innovation, and competitive advantage. Reporting directly to the Chief Executive Officer (CEO), the CTO will lead all aspects of technology, including software engineering, enterprise architecture, infrastructure, cloud operations, cybersecurity, data strategy, and artificial intelligence (AI) initiatives.

This executive will partner closely with Product, Operations, Sales, and other business leaders to deliver scalable, secure, and customer-centric technology solutions while driving operational excellence and advancing our financial platform to more than one million Americans. The CTO will also champion the strategic adoption of AI and emerging technologies to improve internal efficiency, enhance customer experiences, accelerate product innovation, and create new business value.

The ideal candidate is an experienced technology executive with a proven track record leading engineering organizations in a high-growth SaaS or technology environment, successfully delivering modern cloud-based platforms, and implementing AI-driven solutions that produce measurable business outcomes.

• Leadership & Team Management: Build, mentor, and develop a high-performing technology team, fostering a culture of collaboration and continuous learning.
• Artificial Intelligence & Innovation: Lead the company's AI strategy by identifying, implementing, and scaling AI-driven solutions that enhance products, improve operational efficiency, and drive business innovation.
• Technology Strategy & Innovation: Define and execute a technology strategy that supports business objectives, scalability, and operational efficiency.
• Technical Architecture & Development: Oversee the design and implementation of robust, scalable, and secure software solutions and IT infrastructure.
• Technology Operations & Security: Ensure high performance, uptime, and data integrity through effective infrastructure, network, data management, and security protocols.
• Cloud & Digital Transformation: Drive digital transformation initiatives, including cloud adoption, automation, and modern development practices.
• Vendor & Partner Management: Evaluate and manage relationships with technology vendors and partners to ensure optimal solutions and services.
• Cross-functional Collaboration: Partner closely with Product leadership to define and deliver technology capabilities that support the product roadmap, improve customer experience, and accelerate innovation.
• Risk Management & Compliance: Identify and mitigate technology-related risks, ensuring compliance with data privacy and security regulations.
• Business Continuity & Disaster Recovery: Develop and implement disaster recovery and business continuity strategies.
• Data Strategy & Governance: Establish enterprise data strategy and governance to ensure data quality, accessibility, security, and compliance while enabling analytics and AI initiatives.

• 15+ years of progressive technology leadership experience, including senior executive roles, preferably within fintech, SaaS, payroll, HR technology, or other highly regulated software industries.
• Deep expertise across the Microsoft technology ecosystem, including Azure cloud services, .NET, SQL Server, and modern enterprise application architecture.
• Proven success building, leading, and scaling…