Leon CaldwellChief Product Officer · Essays & perspective
Halvery revenue, 2025
C$164M
Fare platform, trip planning and specialised-transit booking for 49 agencies
Product colleagues led
205
Product management, design, accessibility, localisation, data and operations
Fare taps processed in 2025
420M
On about 11,200 validators at 31 agencies

Transit software should be specified for its worst morning and its least-served rider, then priced so that an agency's fare policy never moves our revenue.

I am the chief product officer of Halvery Transit Systems Inc., a fictional Winnipeg company that builds the software Canadian public transit agencies use to collect fares, tell riders when the bus is coming and book specialised transit for people who cannot use a fixed route. Forty-nine agencies in eight provinces and Yukon run at least one of our three products. In 2025 our fare platform processed about 420 million taps, our trip-planning app had 1.7 million monthly users in English and French, and our booking system scheduled 2.6 million door-to-door trips. Revenue was C$164 million.

Our customers are public bodies. They buy through open competitions, answer to councils and provincial ministries, publish their decisions, and carry accessibility, official-language and privacy duties that a consumer app can treat as optional. I have stood on both sides of that relationship. I spent nine years inside two agencies, first planning routes in Saskatchewan and then running rider information for a bilingual commission in eastern Ontario, before joining a Toronto scheduling-software vendor and then a Montréal car-sharing operator. I came to Halvery in 2015 and have led its product organisation since April 2019.

The decisions I am asked about most often cost us money first. I held a fare launch for eleven months because our validators had not survived a prairie January. I made French and English ship in the same release or not at all. I moved our fare contracts off a percentage of fare revenue so that free fares for children and fare capping would never reduce our income. In each case the agency signed the contract, but a rider would live with the result, and I wanted the product to answer to that rider.

A launch held until the hardware had seen a winter

Validators in a winter pilot in early 2022 failed to read cards on up to 11 per cent of cold starts below minus thirty. We deferred a C$4.2 million milestone, retrofitted 2,300 units for C$1.9 million and launched in April 2023. Cold-start failures have since stayed below 0.5 per cent.

French at parity, release after release

Since November 2020 no Halvery rider feature has shipped in English before French. The French-language rating of our app rose from 3.1 to 4.4, and three Quebec agencies with contracts worth C$19 million together have chosen or renewed with us.

Vendor revenue taken out of fare policy

Fourteen of nineteen fare contracts moved from a share of fare revenue to fixed fees per vehicle and station by 2025, and all fourteen renewed. Six of those agencies have since introduced fare capping or free fares for children without renegotiating a clause.

The telephone kept as an equal booking channel

Our specialised-transit engine offers phone agents and app users the same trips at the same moment. Online booking rose without incentives from 22 to 49 per cent of trips by 2025, and average call handling time fell by 31 per cent.

Current focus

I am preparing our board's decision on extending the fare platform to regional and intercity operators, where agencies want one rider account across several services and the privacy questions multiply. Alongside it, I am rewriting our product requirements so that each feature describes its behaviour with no network, with a frozen screen and with a screen reader before it describes a good day.

Conversations I welcome

I am not looking to leave Halvery. With our board's consent, I would consider one independent directorship at a Canadian organisation where software carries a public obligation: a provincial Crown corporation, a listed transportation or infrastructure-services company, or a privately held company serving public-sector customers that neither competes with Halvery nor sells to it. Twenty-four days a year is what I can honestly commit alongside my role. I also accept a few invitations to speak to transit, accessibility and public-procurement audiences.

Beyond the page

The record behind the perspective.

In the boardroom

  • Thornhaven Access SocietyDirector, not-for-profit board; member of the finance committee · 2017–present

Formation

  • Bachelor of Engineering, Civil EngineeringAspenvale University · 1998
  • Graduate Diploma in Public Administration (part-time)Wenlock School of Public Affairs · 2006
Leon is the executive who most often asks our board to spend money for a reason that will not show in next quarter's figures. When he held the fare launch in 2022, he brought us the milestone, the retrofit cost and the risk to riders in one paper, and he was right about all three.
Annika StrandholmFictional chief executive officer, Halvery Transit Systems Inc.
The full record ↗

Contact

I am not looking to leave Halvery. With our board's consent, I would consider one independent directorship at a Canadian organisation where software carries a public obligation: a provincial Crown corporation, a listed transportation or infrastructure-services company, or a privately held company serving public-sector customers that neither competes with Halvery nor sells to it. Twenty-four days a year is what I can honestly commit alongside my role. I also accept a few invitations to speak to transit, accessibility and public-procurement audiences.

  • Board appointments
  • Speaking invitations