Chief Operating Officer (COO)

OTT Pay Inc. is an established, fully funded fintech company focused on delivering streamlined financial payment solutions. With a strategic focus on both acquiring and issuing business, we are developing a mobile-first platform that offers a wide range of financial services, loyalty programs, and innovative products, including credit cards, payment solutions, e-commerce, gift cards, and more. We are a results-driven, forward-thinking organization that values goal orientation and continuous improvement.

At OTT Pay, you will find abundant opportunities for professional growth, working alongside a talented and diverse team from various industries. Our collaborative and innovative environment fosters learning and development, empowering you to excel and make a tangible impact. This is a unique chance to join a company dedicated to reshaping financial solutions for the future.

We are seeking an experienced, strategic, and results-driven Chief Operating Officer (COO) to serve as the operational engine of the company. Reporting directly to the CEO, the COO will oversee day-to-day administrative and operational functions, translate the company's vision and strategy into actionable, high-impact business processes, and ensure the organization scales effectively and efficiently to meet rapid growth objectives. A key component of this role includes evaluating, piloting, and embedding AI and Generative AI technologies into core business processes.

What’s in it for you: 

• Competitive salary depending on experience, plus performance bonus 

• Extended Health, Dental, and Vision Benefits 

• Life and Disability Insurance 

• Generous Vacation Leave 

• Centrally located modern and spacious offices close to Eglinton and Leslie 

• Free use of onsite Gym and Sports Facilities, and regular Company Social Events 

• Learning and Professional Development Support 

• Tremendous opportunities for Growth and Development 

How you will contribute: 

Strategic Operational Leadership & Scalability

• Translate the company’s vision and long-term strategy into clear, executable, and measurable operational plans across all departments.
• Design, implement, and optimize processes and systems to maximize efficiency, productivity, and organizational scalability.
• Establish KPIs and operational metrics, monitor performance, and take corrective actions to ensure company-wide targets are met.
• AI & Generative AI Implementation Strategy
• Develop and lead the strategy for identifying and implementing AI/GenAI tools across non-product departments (Marketing, Sales, Customer Support, HR, Finance).
• Drive operational leverage by using AI to automate repetitive tasks, improve data analysis, and accelerate decision-making, defining KPIs for AI-driven productivity gains.
• Oversee proof-of-concept projects, vendor management, and governance frameworks to ensure secure, ethical, and compliant use of AI technologies and data.
• Collaborate with the CTO/Head of Engineering to ensure internal AI initiatives align with technical architecture and security standards.

Cross-Functional Management & Alignment

• Partner with the executive team (CFO, CTO, CSO, etc.) to ensure resource allocation and departmental activities align with strategic goals.
• Work with Product and Engineering to ensure operational processes support the product roadmap, development cycles (DevOps/CI/CD), and quality assurance.
• Collaborate with Sales and Marketing leadership to optimize the end-to-end sales and customer lifecycle, including lead-to-cash processes, CRM utilization, and forecasting.

Customer Success and Service Delivery

• Oversee Customer Success, Onboarding, and Support teams to ensure exceptional customer satisfaction, strong retention, and maximized customer lifetime value (LTV).
• Implement best practices in customer support and professional services to ensure timely, effective resolution of customer issues.

Financial & Administrative Stewardship

• Partner with the CFO to manage the operating budget, control costs, and lead initiatives that support financial health and profitability.
• Ensure operational compliance with all legal, regulatory, and industry standards (SOC 2, ISO, GDPR), proactively managing risk.

Leadership and Culture

• Lead, mentor, and inspire executives and managers, fostering a culture of accountability, continuous improvement, and ownership.
• Champion OTT Pay’s values, prioritizing an inclusive, positive, and engaging work environment that attracts and retains top industry talent.

What you bring to the table: 

 Experience & Expertise

• 10+ years of progressive leadership experience, including 5+ years in an executive operational role (COO, VP Operations, etc.) within SaaS or high-growth tech environments.
• Demonstrated experience scaling operations and optimizing processes during periods of rapid growth.
• Proven track record leading digital transformation and AI/ML adoption initiatives in large or fast-scaling organizations.
• Strong understanding of SDLC, product management, DevOps, and modern cloud technologies.
• Experience managing P&L, developing budgets, and leveraging financial metrics for decision-making.

Education

• Bachelor’s degree in Business, Engineering, Computer Science, or related field; MBA or advanced degree preferred.

Skills

• Strategic thinking and advanced problem-solving capabilities.
• Highly effective decision-making abilities.
• Exceptional verbal and written communication.
• Strong technical fluency in AI, Machine Learning, and Generative AI applications (as a strategic leader, not necessarily a data scientist).

Office Location: 1123 Leslie Street, North York 

Schedule: Mon – Fri, 9:00am to 5:30pm 

OTT Financial Group is committed to fostering an inclusive and accessible environment where all employees feel valued and respected, and where every employee can realize their potential. We are committed to providing reasonable accommodation, if required, and will work with you to meet your needs. We appreciate all applicants for their interest; however, only those candidates selected for an interview will be contacted.