Chief Technology Officer

Opportunity to Progress to Chief Product and Technology Officer

Bootstrapped SaaS Fintech

Greater Toronto Area

Onsite

Company Overview

Our client is a profitable, bootstrapped SaaS fintech company generating over $5M in annual recurring revenue. The organization employs approximately 20 full time team members supported by an offshore development partner of approximately 20 engineers. The business operates with strong capital discipline and is actively preparing for private equity investment within the next 12 to 18 months.

The company is focused on continued Canadian growth alongside expansion into the United States market. Institutional readiness, platform scalability, operational maturity, and security are core priorities as the organization positions itself for its next phase of growth.

This is a confidential search due to the seniority of the role and its expected impact on the leadership structure.

Role Context and Evolution

The Chief Technology Officer will join the Leadership Team and report directly to the President and CEO. This role is designed to strengthen technical leadership, platform scalability, security posture, and operational governance across the organization.

Over time, and potentially on short notice, this role may expand to encompass full Chief Product and Technology Officer responsibilities. The successful candidate must therefore be capable of owning both technology execution and product delivery at an enterprise level.

The role is intended to reduce key person dependency, improve execution discipline, and ensure the platform and organization are fully prepared for institutional diligence and post investment scaling.

Role Summary

The Chief Technology Officer, with future progression to Chief Product and Technology Officer, is accountable for the end to end product and technology function. This leader balances strategic vision with hands on execution and ensures the platform is secure, scalable, well documented, and operationally resilient.

This role plays a critical part in enabling revenue growth, customer retention, and long term valuation through disciplined technology leadership.

Location and Work Model

This is a hybrid role based in downtown Toronto. The successful candidate is expected to be onsite three to four days per week, excluding periodic business travel for customer meetings, conferences, and partner engagements.

Reporting Structure and Team Leadership

The CTO oversees two core functional areas:

Platform Services

Led by a Platform Services Manager and a team of four to five support and implementation professionals responsible for customer onboarding, platform support, and implementation delivery.

Platform Development

Comprising an internal product and development team of three or more team members, alongside oversight of a subcontracted offshore development team of approximately 20 engineers based in India.

Key Responsibilities

Product and Technology Leadership

Define and execute a capital efficient product and technology roadmap aligned with revenue growth, customer retention, and market expansion.

Own platform architecture, scalability, performance, reliability, and long term maintainability.

Ensure platform modernization while maintaining uptime, security, and customer trust.

Operational and Governance Excellence

Establish repeatable development, release, and support processes aligned with private equity diligence expectations.

Strengthen documentation, architectural clarity, and operational metrics.

Reduce key person dependency through structure, delegation, and process maturity.

Enable transparent reporting on platform health, delivery velocity, and technical risk.

Leadership and Collaboration

Lead and develop internal product, engineering, and platform services leaders.

Provide effective governance and performance management of offshore development partners.

Partner closely with the CEO and executive team on growth strategy, budgeting, and investment readiness.

Serve as a credible technical and product leader with customers, auditors, partners, and future investors.

Security and Compliance

Ensure enterprise grade security, compliance, and risk management practices appropriate for fintech customers in Canadian and US markets.

Partner with internal and external stakeholders to maintain audit readiness and regulatory confidence.

Technical Expertise

Required Experience

Extensive hands on experience with Microsoft .NET MVC and .NET Core in production SaaS environments.

Advanced expertise in Microsoft SQL Server development, optimization, and performance tuning.

Strong experience designing scalable, maintainable, enterprise grade application architectures.

Practical experience with Microsoft Azure infrastructure and platform services, including cost optimization.

Demonstrated success managing SaaS performance, availability, and security in regulated or fintech environments.

Experience modernizing platforms while preserving uptime and customer confidence.

Leadership Attributes

Owner mindset with strong fiscal discipline and accountability.

Hands on, player coach leadership style with deep technical engagement.

Proven ability to lead distributed and offshore development teams effectively.

Strong business acumen with the ability to link technology decisions to revenue growth and valuation.

Clear and confident communicator capable of engaging executives, customers, auditors, and investors.

What Success Looks Like After 12 Months

A clearly articulated and executed product and technology roadmap aligned with revenue and growth objectives.

A stable, scalable, and secure SaaS platform with measurable improvements in performance and uptime.

Mature development and release processes with predictable delivery timelines.

A well governed offshore development model delivering consistent quality and velocity.

Improved security posture, compliance readiness, and audit confidence.

A product and technology organization capable of scaling post investment without significant restructuring.

Increased confidence from customers, partners, and prospective private equity investors.

Ideal Candidate Profile

The ideal candidate is a senior product and technology leader with 10 or more years of experience in SaaS, preferably within fintech or regulated industries. They have successfully scaled platforms in bootstrapped or capital efficient environments and understand private equity expectations.

A relevant university degree is required. Post graduate education or professional designations are considered strong assets.