CTO

AutoPayPlus•Orlando, FL

About The Position

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.

Requirements

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

Nice To Haves

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

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