Chief Technology Officer

CP Payroll, LLC dba ConnectPay•Mansfield, MA

2d•$200,000 - $225,000•Onsite

About The Position

ConnectPay provides comprehensive payroll, finance, and HR solutions specifically designed for small and medium-sized businesses and their employees. Our mission is constantly simplifying the +14,000 state, federal, and local payroll processes jurisdictions 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 +90% annual logo retention behind at ten year 30% CAGR. At ConnectPay, 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. Built on connections, we believe that our employees are our most valuable asset. By fostering a culture of innovation, collaboration, and professional growth, we empower our team to deliver exceptional technologies, products, and service that create meaningful daily impact for our clients and their families. Job Summary The Chief Technology Officer (CTO) is responsible for defining and executing ConnectPay'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 alongside 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.

Requirements

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 high-performing engineering organizations that consistently deliver secure, reliable, and scalable technology solutions.
Demonstrated experience defining and executing enterprise AI strategies, including Retrieval-Augmented Generation (RAG), Model Context Protocol (MCP), Generative AI, intelligent automation, AI agents, and AI-driven business solutions that deliver measurable customer and business outcomes.
Extensive experience architecting and operating cloud-native solutions on Microsoft Azure with a strong emphasis on scalability, security, resilience, observability, and operational excellence.
Strong technical expertise in enterprise software engineering, cloud infrastructure, cybersecurity, data architecture, enterprise integration, and technology operations.
Proven track record leading enterprise modernization and digital transformation initiatives, including cloud migration, platform modernization, application modernization, and engineering process improvement.
Deep understanding of Agile, Scrum, DevOps, CI/CD, quality engineering, and modern software delivery practices.
Strategic business leader with the ability to translate corporate objectives into technology vision, investment strategies, and executable technology roadmaps.
Excellent leadership, communication, executive presentation, and stakeholder management skills, with the ability to influence and collaborate effectively across executive leadership, Board members, customers, partners, and technology teams.
Experience developing technology governance, enterprise architecture standards, cybersecurity programs, disaster recovery strategies, and technology risk management practices.
Demonstrated ability to evaluate emerging technologies and make pragmatic technology investment decisions that balance innovation, cost, risk, and long-term business value.
Bachelor's degree in Computer Science, Engineering, Information Technology, or a related technical discipline required; Master's degree in Computer Science, Engineering, Business Administration (MBA), or a related field preferred.
Demonstration of being a progressive builder, amplifier, and agent of progress!

Responsibilities

Build, mentor, and develop a high-performing technology team, fostering a culture of collaboration and continuous learning.
Lead the company's AI strategy by identifying, implementing, and scaling AI-driven solutions that enhance products, improve operational efficiency, and drive business innovation.
Define and execute a technology strategy that supports business objectives, scalability, and operational efficiency.
Oversee the design and implementation of robust, scalable, and secure software solutions and IT infrastructure.
Ensure high performance, uptime, and data integrity through effective infrastructure, network, data management, and security protocols.
Drive digital transformation initiatives, including cloud adoption, automation, and modern development practices.
Evaluate and manage relationships with technology vendors and partners to ensure optimal solutions and services.
Partner closely with Product leadership to define and deliver technology capabilities that support the product roadmap, improve customer experience, and accelerate innovation.
Identify and mitigate technology-related risks, ensuring compliance with data privacy and security regulations.
Develop and implement disaster recovery and business continuity strategies.
Establish enterprise data strategy and governance to ensure data quality, accessibility, security, and compliance while enabling analytics and AI initiatives.