Leon CaldwellChief Product Officer · Essays & perspective

Leon Caldwell · Chief Product Officer · Canada

From the planning office to the product chair

Chief Product Officer

Halvery Transit Systems Inc.

Sector
Software for public transit: account-based fare payment, trip planning and rider information, specialised-transit booking
Ownership
Privately held; Brackenridge Lane Partners, a Toronto private-equity firm, has held 62 per cent since 2018, with founders and employees holding the rest
Company scale
C$164M revenue and C$29M adjusted EBITDA in 2025
Employees
760
Geography
Winnipeg headquarters; offices in Montréal and Toronto; bilingual support centre in Moncton; customers in eight provinces and Yukon
Reporting to
Chief Executive Officer; presents to the board each quarter and reports twice a year to its Audit and Risk Committee on privacy and accessibility
Team
205 across product management, design and research, accessibility, localisation, data and product operations; seven direct reports
Financial scope
Product organisation budget of C$31M a year; owns pricing and packaging for all three product lines and the roadmap behind C$164M of revenue

Mandate

Turn three products built at different times into one platform agencies can buy in parts, and make the company's product decisions defensible to public customers.

Outcomes

  • Held a fare launch for eleven months until validators passed a field winter; cold-start failures fell from 11 per cent to under 0.5 per cent.
  • Made French and English release together from November 2020; the French-language app rating rose from 3.1 to 4.4.
  • Moved 14 of 19 fare contracts from a share of fare revenue to fixed fees; every converted contract renewed.
  • Raised voluntary online booking of specialised transit from 22 to 49 per cent while keeping the telephone an equal channel.
  • Revenue grew from C$97M in 2018 to C$164M in 2025.

Decisions in context

I became chief product officer in April 2019, a year after Brackenridge Lane Partners bought a majority of Halvery and when the co-founder who had led product and technology retired. The mandate from our chief executive was to make three products, built at different times by different teams, behave as one platform, and to make our product choices defensible to customers who must defend their own choices in public. I lead 205 people with seven direct reports, own pricing and packaging, and present the product plan to the board every quarter. The largest decisions of the period each cost money first: an eleven-month launch delay over cold-weather failures, a language-parity rule that lost an Ontario competition, a pricing change that gave up percentage revenue and a refusal to make specialised-transit booking app-only. Revenue has grown from C$97 million in 2018 to C$164 million in 2025.

Reason for the move

Current role. Not seeking an executive move; considering one independent directorship with the board's consent.

Vice-President, Product, Fares and Rider Information

Halvery Transit Systems Inc.

Sector
Software for public transit: scheduling, fare payment and rider information
Ownership
Founder-owned until a majority sale to a Toronto private-equity firm in 2018
Company scale
C$58M in 2014, rising to C$97M in 2018
Employees
290 in 2015, 520 by early 2019
Geography
Winnipeg headquarters; Montréal office opened in 2016; customers in seven provinces
Reporting to
Co-founder and chief product and technology officer
Team
Grew from 22 to 71; five direct reports
Financial scope
Product lines with revenue of C$41M in 2018; pricing proposals subject to the founders' approval

Mandate

Take the account-based fare product from two pilot agencies to a platform mid-sized agencies could procure, and rebuild the rider app.

Outcomes

  • Took the fare platform from 2 agencies to 17.
  • Launched contactless bank-card payment on buses for the first Halvery customer in 2018.
  • Rebuilt the rider app in both languages; monthly users grew from 240,000 to 1.1 million.
  • Set up the rider accessibility panel in 2017, with fourteen paid members.

Decisions in context

I joined Halvery in February 2015 from Montréal, attracted by a small Winnipeg company that had built an account-based fare product and was running it at two agencies. My job was to turn it into something mid-sized agencies could procure through an open competition, with documentation, accessibility testing and bilingual interfaces that a pilot could survive without. I reported to the co-founder who led product and technology, and the team grew from 22 to 71 people. By early 2019 the fare platform ran at seventeen agencies and our first customer had launched contactless bank-card payment on buses. I also rebuilt the rider app, which grew from 240,000 to 1.1 million monthly users, and in 2017 set up the paid rider accessibility panel that still reviews every rider-facing feature. When the co-founder retired in 2019, the board asked me to lead the whole product organisation.

Reason for the move

Promoted to chief product officer when the co-founder who led product and technology retired in 2019.

Head of Product

Autelia Partage Inc.

Sector
Station-based and free-floating car sharing
Ownership
Privately held; backed by its founders and a Quebec venture fund
Company scale
C$34M in 2014
Employees
180
Geography
Montréal and Quebec City; 1,100 vehicles
Reporting to
Chief Executive Officer
Team
18; three direct reports
Financial scope
Product and app budget of C$4M a year; membership and trip-rate pricing

Mandate

Replace a web-first reservation system with a mobile product and make the service usable through a Quebec winter.

Outcomes

  • Launched the free-floating service and its mobile app in 2013; members rose from 38,000 to 71,000.
  • Cut winter trip cancellations caused by cars that would not start or were snowed in from 9 to 3 per cent.
  • Built snow-clearing parking alerts that warned members before cars could be towed; towing costs fell by 44 per cent.

Decisions in context

Autelia gave me my first consumer product and my first job conducted in French from morning to evening. The company ran 1,100 cars in Montréal and Quebec City, mostly from reserved spaces, and wanted to add free-floating cars that members could find and leave on the street. I reported to the chief executive and led a team of eighteen. Winter shaped almost every decision. We added battery and block-heater checks to vehicle telemetry, routed members away from cars likely to be snowed in, and built alerts for the city's overnight snow-clearing operations so that members could move cars before they were towed. Membership grew from 38,000 to 71,000 and winter cancellations fell from 9 to 3 per cent. I left in early 2015 because I missed working for riders who had no car to fall back on.

Reason for the move

Wanted to return to public transit, where the riders with the fewest alternatives depend on the product.

Product Manager, later Director of Product

Quillfield Transit Software Inc.

Sector
Scheduling, vehicle-location and real-time passenger-information software for transit agencies
Ownership
Privately held until its acquisition by a US industrial software group in 2012
Company scale
C$46M in 2011
Employees
340
Geography
Toronto headquarters; customers in Canada and the northern United States
Reporting to
Vice-President, Products; from 2010, the Chief Executive Officer
Team
Four as product manager; sixteen as director of product
Financial scope
Product lines with C$19M of annual revenue; no pricing authority

Mandate

Turn a scheduling package into a real-time information product that agencies could publish directly to riders.

Outcomes

  • Launched the company's first real-time arrival feed and rider-facing web planner, adopted by 23 agencies by 2012.
  • Introduced an export of schedules and predictions in the open format that third-party trip-planning apps read.
  • Built the first bilingual interface, which opened four contracts in Quebec and New Brunswick.

Decisions in context

I crossed to the vendor side in January 2008 to see how the systems I had bought were decided. Quillfield sold scheduling and vehicle-location software to about sixty agencies and had real-time data it was not yet showing to riders. As product manager and, from 2010, director of product, I led the work that turned that data into a public arrival feed and a web trip planner, adopted by 23 agencies by 2012. I pushed for an export in the open schedule format that independent trip-planning apps use, against colleagues who saw it as giving data away; agencies valued it more than any feature we sold. I also led the first bilingual interface, which opened four contracts in Quebec and New Brunswick. When a US industrial software group bought the company in 2012 and moved product management south, I chose not to follow.

Reason for the move

Left after the 2012 acquisition moved product management to the United States.

Manager, Customer Information Systems

Rideaumont Transit Commission

Sector
Public transit: bus and paratransit services
Ownership
Municipal transit commission governed by a board of appointed councillors and citizen members
Company scale
C$118M operating budget in 2007, about 46 per cent covered by fares
Employees
1,450
Geography
A bilingual region of eastern Ontario; 410 buses
Reporting to
Director of Customer Services
Team
Eleven
Financial scope
Customer-information budget of C$3.2M a year and a C$7M capital project for vehicle location and stop announcements

Mandate

Give riders reliable departure information and bring automated stop announcements to every bus in English and French.

Outcomes

  • Launched a telephone line giving predicted arrivals from bus GPS, handling 9,000 calls a day by 2007.
  • Installed automated bilingual stop announcements on all 410 buses.
  • Cut complaints about missing or wrong schedule information by 37 per cent.

Decisions in context

At Rideaumont I ran customer information for a commission whose riders expected to be served in English and French, and whose board met in public. My team of eleven handled timetables, detour notices and the telephone enquiry line. I led a C$7 million capital project that put GPS units and automated stop announcements on all 410 buses, which allowed us to launch a telephone line giving predicted arrival times; by 2007 it took 9,000 calls a day. The announcements were the harder part: every stop name needed an agreed form in both languages and a recording that blind riders could follow at speed. I presented the project to the commission's board several times, and complaints about schedule information fell by 37 per cent. I also completed my part-time graduate diploma in public administration here. I left to see how the vendors we bought from made their decisions.

Reason for the move

Wanted to help build the systems agencies buy rather than only buy them, and joined a vendor.

Transit Service Planner

Tullybrook Regional Transit Commission

Sector
Public transit: fixed-route bus and specialised transit
Ownership
Regional transit commission owned by two municipalities
Company scale
C$34M operating budget in 2002
Employees
390
Geography
A Saskatchewan city and its neighbouring municipality; 120 buses
Reporting to
Manager of Service Planning
Team
Individual contributor; supervised two seasonal counting staff
Financial scope
Route proposals affecting about C$6M of annual operating cost; no budget authority

Mandate

Plan routes and schedules, run ridership counts and prepare service changes for the commission.

Outcomes

  • Redesigned four routes serving a new hospital and two high schools; weekday boardings on them rose 18 per cent.
  • Built the commission's first model of winter running times, used to set seasonal schedules.
  • Documented the cost of farebox failures in the February 2000 cold, the basis for a winter maintenance programme.

Decisions in context

I joined Tullybrook straight from university as a service planner. The commission ran 120 buses for a Saskatchewan city and its neighbour, and planning there meant riding the routes, counting passengers and writing service-change reports for monthly public meetings. I redesigned four routes around a new hospital and two high schools, and weekday boardings on them rose by 18 per cent. I also built the commission's first model of winter running times, because the published schedule assumed dry roads for six months of snow. The work that mattered most to me later was a short report on the week in February 2000 when the cold put a third of the fareboxes out of action. Nobody had counted what it cost in fares or in drivers' time, and the report led to a winter maintenance programme. I left in 2003 for a larger agency and a role facing riders directly.

Reason for the move

Moved to eastern Ontario to take responsibility for rider information at a larger, bilingual agency.

What I am looking for next

I intend to stay at Halvery through the next stage of the platform. Extending fare payment to regional and intercity operators, rebuilding specialised-transit scheduling around shared vehicles, and completing the move of every product to the same accessibility and language standards will take at least two more years, and I want to finish them. I am also conscious that private-equity ownership has a horizon, and I would want to see the company through any change of ownership with its product commitments to agencies intact.

If I later considered an executive move, it would be to lead product, or the whole business, at a larger organisation whose software serves the public under obligation: a payments or identity company working with governments, a public insurer's digital services, or a transport operator with a large rider-facing platform. I would look for a chief executive who wants product decisions argued in front of the board and a company willing to publish the measures it is judged on.

In the meantime my next chapter is a board one: one independent directorship, taken with Halvery's consent, outside transit.