At Masabi, we’re driving the fare payment revolution, powering the journeys of millions all over the world. We build fare collection platforms that allow riders to seamlessly buy and present tickets for public transport either on their mobile phones, from a ticket machine, or even by tapping their bank card to travel.

Choosing a role here means joining a network of innovators from all walks of life; As Head of Bids, you’ll lead the team behind them, creating compelling tenders, from qualification through to submission, clarifications and award, for transit agencies and operators internationally.

Business Development, Product, Engineering, Services, Legal and Finance all feed into a bid. Your team shapes their input into one answer, built around what the agency has asked for and how they will evaluate it, with the business and technical strategy to match. You will own the pricing and commercial strategy behind it and run the governance that helps the business make the right call at each stage.

You will also build the function itself: the people, the process and the content the team relies on to bid well under real deadlines. Using AI to make the team faster and sharper is part of that, so we win more often in the markets we care about most.

This role is available in a fully remote model for candidates based in Canada

Lead each bid from qualification through to submission and award, partnering closely with BD and keeping the team on top of quality and deadlines Own the pricing and commercial strategy behind every bid, balancing the chance of winning against margin Run the governance that helps the business make the right call at each stage, including which opportunities to pursue and which to let go Share bid risk and recommendations openly with senior leadership, including where the risk is uncomfortable Bring colleagues together across Product, Engineering, Services, Legal and Finance so the technical, commercial and legal content reads as one answer Build the function itself: the people, processes, content and tooling,



including AI that the team relies on to move faster and win more often Support, coach and develop the bids team and help each person grow Build trusted relationships with colleagues and partners, so what we submit reflects what customers genuinely need You have helped win high-value, competitive bids, and you care about the quality of what goes out the door Presenting bid risk to senior leadership does not worry you, including when the recommendation is to walk away Sales and procurement both make sense to you, from either side of the table Familiarity with public procurement for technology solutions Experience in public transport, mobility, or another regulated, tender-led sector Additional languages, given the range of markets we bid into Experience introducing or improving bid tooling, content libraries or knowledge management You don’t need professional experience using AI tools, but we’d expect you’ve experimented with them and are curious about how they can help you learn, solve problems, and work more effectively.

20 days of vacation per year (in addition to public holidays), plus the option to buy an additional 5 days of vacation each year. On top of this, our office is shut every year between Christmas and Current Year, totalling a whopping 28+ days of vacation Private Healthcare and Life Insurance via Trinet Up to CAD$1300 training bugdet per year CAD$325 per year to spend on your home office CAD $50 per month team building Enhanced family leave We offer a dynamic and supportive environment where your skills in writing compelling proposals and managing complex bid processes can make a significant impact. We are a network of innovators from all walks of life, passionate about making a difference.

We welcome applications from underrepresented groups, including disabled and neurodivergent people, and can make adjustments at any stage of the process. Encouraged to Accelerate – Masabi is going places and our people are in the driving seat. Whether you’re taking the direct route or exploring new paths, we support your journey.

📌 Remote Head of Bids (Winnipeg)
🏢 Bilinguallink
📍 Winnipeg