Director, CTO Office

Tucows; Toronto; Hybrid; CAD 137,000 - 154,000; Full time

Job summary

An established industry player is seeking a Director of the CTO Office to drive strategic initiatives and cross-functional collaboration in a remote-first environment. This high-impact role involves working closely with the CTO and senior leadership to ensure alignment across Engineering, Product, and Operations. The ideal candidate will have extensive experience in program management, a strong attention to detail, and the ability to influence teams without formal authority. If you thrive in dynamic settings and enjoy solving operational challenges, this opportunity is perfect for you.

Qualifications

• 8+ years experience in program management or similar roles.
• Strong communicator with the ability to influence teams.
• Demonstrated ability to drive cross-functional projects.

Responsibilities

• Help shape and lead strategic initiatives across departments.
• Partner with leadership to align platform and product delivery.
• Assist the CTO with board-level strategic deliverables.

Skills

Program Management

Product Operations

Strategic Planning

Cross-Functional Collaboration

Communication

Technical Understanding

Job description

Wavelo is a SaaS business on a mission to make telecoms a breeze.

We provide flexible software that modernizes how communication service providers (CSPs) do business, helping them drive more value, focus on customer experience, and scale their operations faster.

What's New at Tucows

As part of Tucows (NASDAQ:TCX, TSX:TC)—one of the world’s largest Internet services companies—Wavelo is backed by outstanding resources and talent. We embrace a people-first philosophy that is rooted in respect, trust, and flexibility. We believe that whatever works for our employees is what works best for us. It’s also why the majority of our roles are remote-first, meaning you can work from anywhere you can connect to the Internet!

The work we do genuinely changes lives. If this sounds exciting, we’d love to hear from you!

Role Overview: We’re hiring a Director of the CTO Office to operate as an extension of our CTO. This role is a blend of strategic program management, cross-functional coordination, and initiative leadership. This role is about driving clarity, alignment, and momentum across Wavelo’s most critical projects, with the authority to speak and act on behalf of the CTO when needed.

This person will:

• Work hand-in-glove with the CTO to execute on company-wide priorities.
• Drive alignment across Engineering, Product, Technical Operations, and R&D.
• Interface with Sales, Marketing, Finance, HR, and Legal to ensure smooth collaboration and unblock cross-functional efforts.
• Jumpstart and co-own high-impact, ambiguous projects that need structure, definition, and traction.

This is a remote position with some in-office requirements in Toronto.

Key Responsibilities:

• Help shape and lead strategic initiatives. A good example would be formalizing a feature release process in collaboration with Product and Engineering.
• Partner with senior leadership to align platform and product delivery, drive internal reporting, and prepare for budget planning.
• Work with HR, Finance, Security and Legal to ensure org-wide coordination, budget and support requests to/from the CTO office, and maintain internal service levels.
• Assist the CTO with board-level or strategic deliverables, including materials for the CEO, external stakeholders, and investors.

Ideal Candidate Profile:

• 8+ years experience in program management, product operations, strategy, or similar roles.
• Highly organized with strong attention to detail and follow-through.
• Demonstrated ability to drive cross-functional projects with high ambiguity and tight timelines.
• Comfortable making decisions, fostering open dialogue, and holding teams accountable with empathy and clarity.
• Strong communicator with the ability to influence without formal authority.
• Technically conversant — you won’t need to code, but you should be fluent enough to understand architectural discussions and platform constraints.
• Hands-on and unafraid to jump into the weeds when needed.

Nice to have:

• Experience in a startup or high-growth environment
• Background in modern software architecture and the software development lifecycle (SDLC)
• Familiarity with building or scaling SaaS platforms
• Exposure to event-driven systems and architectural patterns

Why This Role Matters: This is a high-impact role in a high-leverage part of the company. You’ll be trusted with wide latitude and real responsibility to help the CTO — and by extension, Wavelo — execute faster and better. If you thrive in environments where you wear multiple hats, love solving operational puzzles, and want to shape the direction of a product-led tech company, this might be your role.

The base salary range for this position is $137,790 - $153,100. Range shown in $CAD for Canadian residents. Other countries will differ. Range may vary on a number of factors including, but not limited to: location, experience and qualifications. Tucows believes in a total rewards offering that includes fair compensation and generous benefits

Want to know more about what we stand for? At Wavelo and Tucows we care about protecting the open Internet, narrowing the digital divide, and supporting fairness and equality.

We also know that diversity drives innovation. We are committed to inclusion across race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status or disability status. We celebrate multiple approaches and diverse points of view.

We will ensure that individuals with disabilities are provided reasonable accommodation to participate in the job application or interview process, to perform essential job functions, and to receive other benefits and privileges of employment. Please contact us to request an accommodation.

Tucows and its subsidiaries participate in the E-verify program for all US employees.

Learn more about Tucows, our businesses, culture and employee benefits on our site here.