Chief Technology Officer (CTO)
We are seeking an experienced Chief Technology Officer to provide long-term technology leadership for a mature, founder-built fintech organization entering its next phase of scale.
This role is designed for a technology executive who can steward an established platform, organization, and culture, while progressively assuming full ownership of technology strategy, execution, and accountability over time. The CTO will work closely with existing technical and business leaders to ensure continuity, resilience, and thoughtful evolution of our systems and teams.
This is not a turnaround or greenfield role. Success requires respect for institutional knowledge, comfort operating within a disciplined operating model, and the ability to lead through influence, trust, and clarity.
Key Responsibilities
Technology Strategy, AI & Innovation
- Define and evolve the company’s long-term technology strategy in alignment with business objectives
- Lead the responsible adoption of AI and automation across both operational systems and internal engineering practices
- Identify opportunities to apply AI/ML to improve:
- Platform capabilities and customer experience
- Internal efficiency, tooling, and developer productivity
- Decision-making, analytics, and risk management
- Ensure AI initiatives are pragmatic, secure, explainable, and aligned with regulatory and ethical expectations
- Balance innovation with platform stability, compliance, and operational continuity
Organizational Stewardship & Operating Discipline
- Serve as the ultimate executive owner of all technology systems, platforms, and technical risk
- Provide executive oversight of software engineering, data, infrastructure, security, and IT functions
- Lead within a mature EOS (Traction) operating environment, including:
- Clear ownership and accountability
- Measurable outcomes and scorecards
- Quarterly priorities (Rocks) aligned with company strategy
- Partner closely with a dedicated project management function to ensure:
- Clear scope, sequencing, and prioritization of initiatives
- Predictable delivery and transparent tradeoffs
- Alignment between strategic objectives and execution plans
- Reinforce disciplined execution through consistent planning, review, and retrospective rhythms across technology teams
- This role is not expected to personally manage projects, but is accountable for ensuring that project management and delivery disciplines are strong, respected, and effective across the organization
Team Leadership & Collaboration Model
- Lead and support a technology organization that is primarily in-house and on-prem, augmented by selective remote and external resources
- Champion the value of in-person collaboration, mentorship, and cross-functional interaction as a core part of the company’s culture
- Thoughtfully integrate remote or offshore resources where appropriate, while maintaining strong alignment, accountability, and cohesion with in-house teams
- Build teams and operating practices that prioritize trust, communication, and shared ownership over purely distributed execution
Platform & Architecture Oversight
- Guide architectural direction across a Microsoft-centric stack (.NET, Azure, SQL Server), including both cloud and on-prem components
- Ensure platform reliability, scalability, performance, and observability
- Oversee technical debt management and modernization efforts with a long-term, incremental approach
- Establish standards and guardrails that allow teams to innovate safely and consistently
Risk, Security & Compliance
- Maintain executive accountability for PCI compliance, data protection, and security posture
- Partner with compliance, legal, and operations teams to manage technology-related risk
- Ensure systems, processes, and AI usage meet regulatory, audit, and governance expectations
Cross-Functional & Executive Leadership
- Collaborate closely with executive leadership on product strategy, roadmap planning, and feasibility tradeoffs
- Translate technical complexity, AI capabilities, and risk into clear business context for non-technical stakeholders
- Act as a trusted technology advisor at the executive and board level
Leadership Continuity & Transition
- Participate in an intentional leadership continuity process, including a period of shared authority and knowledge transfer
- Build trust across the organization through listening, transparency, and consistency
- Gradually assume full CTO ownership as part of a planned, long-term transition
Required Qualifications
- 10+ years of software development experience with at least 5+ years in senior technology leadership roles (CTO, VP Engineering, Director+)
- Deep experience with Microsoft technologies (.NET, C#, Azure, SQL Server)
- Proven ability to lead technology organizations in regulated environments (fintech, payments, financial services, or similar)
- Demonstrated experience introducing AI, automation, or advanced analytics into production environments
- Experience stewarding mature platforms while evolving architecture over time
- Strong understanding of security, compliance, and data protection in financial systems
- Demonstrated experience operating within structured Agile delivery models
- Strong appreciation for disciplined project management practices, including planning, estimation, dependency management, risk tracking, and delivery accountability
- Demonstrated ability to operate effectively within structured operating frameworks such as EOS (Traction) or equivalent
- Experience leading predominantly in-house teams, with thoughtful use of remote or offshore resources as augmentation
- Excellent communication skills across technical and non-technical audiences
Preferred Attributes
- Experience inheriting or partnering with founder-led technology organizations
- Comfort operating in environments where authority and ownership are phased
- Long-term leadership mindset with interest in sustained organizational stewardship
- Experience using AI to enhance both product capabilities and internal engineering effectiveness
- Familiarity with Azure DevOps tooling and enterprise-scale Agile execution
Final Notes
This role is well-suited to a technology leader who values stewardship, continuity, in-person collaboration, and long-term ownership over rapid transformation or fully distributed operating models.
