Chief Technology Officer

Accountabilities

• Develop and lead a multi-year technology strategy and roadmap aligned with long-term organizational goals, ensuring the technical vision is understood and adopted across the business.

• Establish a customer-centric, problem-first product development approach that ensures teams understand user needs, business challenges, and desired outcomes before committing to technical solutions.

• Identify emerging technologies, market opportunities, partnerships, and potential acquisitions that can strengthen existing products and create new sources of value.

• Advise executive leadership on technology investments, build-versus-buy decisions, strategic partnerships, acquisitions, and other major technology initiatives.

• Define the architectural vision and engineering principles for secure, scalable, configurable, modular, repeatable, and maintainable systems that can evolve as customer and business needs change.

• Promote platform thinking through reusable services, APIs, shared components, and common capabilities that can support multiple products and business units.

• Lead modernization of the technology portfolio by balancing investment in existing platforms with technical debt reduction, consolidation, modernization, and next-generation capabilities.

• Lead the engineering organization with a culture centered on ownership, craftsmanship, continuous improvement, pragmatic decision-making, quality, reliability, and security.

• Advance modern engineering practices while balancing speed of delivery with operational resilience, product quality, cybersecurity, and long-term maintainability.

• Support the organization's transition toward Agile methodologies and Scrum-at-Scale, helping teams adopt effective delivery practices and continuous improvement.

• Build strong partnerships across departments, creating alignment around technology priorities, timelines, resources, dependencies, and organizational goals.

• Translate complex technical concepts into clear business language for executives and non-technical stakeholders while bringing business context and customer priorities back to technical teams.

• Build, lead, and develop a high-performing technology organization through organizational design, leadership development, succession planning, workforce strategy, and recruitment of critical technical talent.

• Establish and maintain appropriate standards for security, privacy, compliance, and data governance, including requirements relevant to government agencies, courts, and criminal justice environments such as CJIS.

• Oversee technology investment, performance, operational resilience, and resource allocation to ensure systems remain reliable, scalable, secure, and prepared for business continuity.

• Establish effective technology governance and risk-management practices in partnership with Security, Cloud Operations, IT, Legal, and business leadership to manage architectural, cybersecurity, regulatory, and third-party technology risks.

Requirements:

• Bring 12+ years of software engineering experience, including at least 5 years in senior technical leadership positions such as CTO, VP of Engineering, Head of Engineering, or a comparable role.

• Demonstrate proven experience leading and scaling engineering organizations and enterprise software platforms in complex technology environments.

• Possess deep expertise in software and systems architecture, including distributed systems, cloud-native architecture, APIs, data platforms, scalability, security, and modern engineering practices.

• Bring strong product judgment and experience making customer-driven product and technology decisions based on real user needs and business outcomes.

• Demonstrate a track record of establishing compelling technical visions and successfully aligning engineering teams, executives, and other stakeholders around strategic priorities.

• Have excellent communication and collaboration skills, with the ability to engage effectively with executives, engineers, customers, partners, and non-technical stakeholders.

• Experience in government technology, justice or court systems, legal technology, or other regulated public-sector environments is highly desirable.

• Experience incubating new products or working within a startup, innovation lab, venture environment, or similarly entrepreneurial setting is preferred.

• Hands-on experience applying artificial intelligence, machine learning, and data-driven technologies to real-world products is preferred.

• Experience working in Agile environments or formal training in Scrum or Agile methodologies is expected.

• Hold a bachelor's degree in Computer Science, Engineering, or a related technical discipline; an advanced degree is considered an advantage.

• Be comfortable operating as a strategic technology leader while remaining close enough to engineering, architecture, product, and customer needs to make informed decisions.

• Candidates must be eligible to work in Canada without employer-sponsored visa or work authorization support.

Benefits:

• Competitive annual compensation of CAD $225,000–$275,000 for the Canada-based position.

• Quality medical, dental, and vision coverage.

• Discretionary profit-sharing opportunities for eligible employees.

• Competitive paid time off and paid holidays.

• Canadian GRRSP retirement program.

• Annual professional development funding of at least $1,500 USD per employee, depending on role.

• Access to extensive book libraries to support personal and professional development.

• Opportunities to travel between offices and to client locations.

• Opportunity to lead technology strategy for software that supports foundational justice and public-sector systems.

• Exposure to enterprise architecture, modernization, AI, cloud technologies, cybersecurity, data governance, and regulated technology environments.

• Significant influence over technology organization design, engineering culture, product strategy, and long-term technical direction.

• Opportunity to work with experienced technical, executive, product, and cross-functional teams on technology with meaningful societal impact.