Leon CaldwellChief Product Officer · Essays & perspective

Leon Caldwell · Chief Product Officer · Canada

What I would bring to a board where software carries a public duty

My contribution to a board

I would bring a board three things that are often thin when an organisation serves the public through software.

The first is an operator's view of large digital programmes. I have launched fare systems, rebuilt rider apps and changed a booking system that people with disabilities rely on to reach dialysis and work. I know where such programmes usually go wrong: in the conditions nobody tested, in the language and accessibility work left to the end, and in contracts whose incentives quietly point the wrong way. I can read a management paper on a digital programme and ask for the part that is missing.

The second is fluency in public obligations. I spent nine years inside two transit agencies and have sold to public buyers for most of the eighteen years since. I understand procurement rules, the difference between capital and operating budgets, the official-language and accessibility expectations placed on public bodies, and how privacy law treats a public body differently from a company. A Crown corporation, or a company that serves governments, needs directors who treat those obligations as part of the business rather than a fence around it.

The third is a habit of putting product risk before a board in plain numbers. At Halvery I report privacy incidents, accessibility gaps and degraded-mode failures to our Audit and Risk Committee in the same form as revenue: what happened, how many riders, what it cost and what we changed. I would ask management for the same.

I should be clear about my limits. I am financially literate and have reviewed audited statements for nine years as a not-for-profit director, but I am not an accountant. Canadian rules for most listed companies expect audit-committee members to be independent and financially literate, and I would serve on such a committee if asked, but I would not seek its chair. My strongest contribution is on risk, technology and privacy.

My first year on a board

My first year would be spent learning before advocating. Before the first meeting I would ask for the strategy, two years of board and committee minutes, the risk register, the latest internal-audit reports and any correspondence with regulators or privacy commissioners. I would also ask to use the organisation's main public-facing services as an ordinary customer would, including its telephone channel and its French service, and to read a sample of its complaints.

In the first six months I would meet the chief executive, the chief financial officer, the heads of technology, privacy and internal audit, and the external auditor, and ask each of them the same question: which risk does this board discuss too little? I would visit at least one operating site, because the digital service a board approves is rarely the one the front line ends up using.

For the rest of the year I would serve on committees without seeking a chair. I would keep a running list of the questions I had asked and whether the answers changed anything, and at the year's end I would give it to the board chair as part of the board's evaluation. If my questions had been more about my own industry than about theirs, I would want to be told.

Conflicts and their management

The plainest conflict is with my employer. I would not sit on the board of any transit agency, transit commission or regional transportation authority in Canada, because each is a Halvery customer or could become one. Nor would I join a company that supplies fare, vehicle-location, payment-processing or booking technology to transit, because each is a competitor, a partner or a supplier of ours. That rules out much of the sector I know best, which is exactly why my search lies outside it.

Brackenridge Lane Partners owns a majority of Halvery and holds other businesses. Before any appointment I would ask the firm for a list of its current holdings and decline a board with a commercial relationship with any of them, unless the appointing board, knowing the facts, judged it immaterial.

The second conflict is time. Halvery's board meets quarterly, and our heaviest seasons are winter launches and the spring procurement cycle. I would fix a year's meeting dates in advance, reserve twenty-four days including preparation, and tell the chair at once if Halvery's demands changed. If an unforeseen relationship emerged after appointment, I would disclose it in writing, leave the room for the relevant discussion and offer to resign if it was likely to recur.

My independence statement

I am an executive of Halvery and hold a small equity interest through its management incentive plan. Canadian securities rules and most Crown-corporation appointment processes ask, in different words, whether a director has a relationship that could reasonably be expected to interfere with independent judgement. That is for the appointing board to decide on full facts, and I would give it all of them: my Halvery role and equity, the other holdings of Brackenridge Lane Partners as far as I can learn them, my directorship at Thornhaven Access Society and any customer or supplier link, however indirect. I would not call myself independent until that board had concluded that I was.

Judgement in practice

01

Telling a customer before the forensics were finished

In March 2024 a misconfigured analytics export sent trip records for about 3,100 riders of one agency to a planning contractor who should have received only aggregated data. The contractor reported it the same day and confirmed deletion. Our general counsel wanted a forensic review completed before we told the agency, which was responsible for the records under its provincial privacy law. I recommended telling the agency within 48 hours, with what we knew and what we did not, so that it could decide on its own obligations to riders and to its privacy commissioner. Our chief executive agreed. The agency notified the affected riders. I reported the incident and its causes to our Audit and Risk Committee at its next meeting, and every export of identifiable data now needs two approvals. As a director I would ask management whether a customer, a regulator or a rider has heard about an incident before the board has.

02

Recommending that the board decline a data partnership

In 2022 a location-analytics company offered Halvery about C$1.2 million a year for de-identified trip-planner and tap data across our customers, to be resold to retailers and property developers. Our contracts arguably allowed it, and the revenue would have helped in a year when our pricing change was reducing income. I recommended that the board decline. The agencies had not collected the data for that purpose, their riders had not been asked, and movement data is harder to de-identify than it sounds, because a handful of origins and destinations can often identify a person. Two directors argued that a competitor would simply take the money. The board declined and asked me to write the restriction into every new contract. On another board I would ask of any new revenue built on data whether the people it describes would recognise it as the purpose they agreed to.

03

Disclosing an accessibility gap before customers found it

In 2025 an internal review found that a redesign of our trip planner had broken screen-reader navigation in the list of route options on one phone platform for nine weeks. No agency had noticed and no rider had complained in writing. I told all 38 agencies that offer the app within the same week, released a fix twelve days later and reported the gap to our Audit and Risk Committee with the release-process change that would have caught it. Our sales leadership feared the disclosure would damage two bids in progress. One evaluator asked about it, and we kept both bids. The lesson I would carry to a board is that a disclosed gap with a dated fix is a manageable matter, while a hidden one becomes a question about the whole organisation.

Committee contribution

Chair and member readiness
CapacityCommittees
Ready to chairA technology, cyber-security and privacy committee, after a year as a member
Ready to joinRisk committee · Technology or cyber-security committee · Governance and nominating committee

Capacity and preferences

Time available
24 days per year
Current directorships
1
Sectors
Provincial Crown corporations in public insurance, utilities or transportation · Infrastructure and transportation services · Software and payment businesses serving public-sector customers outside transit · Health and social-service organisations with large client-facing digital services
Company type
A Canadian Crown corporation, a TSX-listed company or a privately held company with an independent board, where digital services carry public obligations and there is no commercial relationship with Halvery
Company stage
In the middle of a large customer-facing system change, where the board wants a member who has delivered one for public customers and seen one fail

The seat I am pursuing

I am looking for one independent seat on the board of a Canadian organisation that delivers an essential service through digital systems to a public that cannot easily go elsewhere. A provincial Crown corporation in public insurance, utilities or transportation would fit, as would a TSX-listed infrastructure-services company or a privately held software company with an independent board that serves governments outside transit. I would expect revenue somewhere between C$300 million and C$3 billion: large enough to need a technology and privacy committee, small enough that one director's questions are heard.

I would like to join a risk or technology committee and, after a year, chair a committee on technology, cyber-security and privacy if the board has one or wants one. I would also serve on a governance and nominating committee. I am not seeking a second seat while I remain an executive, nor a paid advisory role at a company that sells to transit agencies. What I can offer is the view of someone who has built the kind of system such boards approve, and has watched one fail on a cold morning.

Board and committee exposure

Presented to the Board or a committee

Halvery Transit Systems Inc.

Board of directors: product strategy, annual product plan, pricing changes and major bids

April 2019–present

Presents the product plan and every pricing change at quarterly board meetings; not a director and holds no vote.

Reported to a committee

Halvery Transit Systems Inc.

Audit and Risk Committee: privacy, product-related security incidents and accessibility compliance

April 2019–present

Reports twice a year, and between meetings on any incident affecting rider data.

Served as a director

Thornhaven Access Society

Board of a Winnipeg not-for-profit providing travel training and accessible-transportation advocacy; member of its finance committee

June 2017–present

Elected director in 2017 and re-elected every two years since; reviews budgets, audited statements and the society's provincial funding agreements.

Presented to the Board or a committee

Rideaumont Transit Commission

Commission board: rider-information projects and the bilingual stop-announcement programme

2004–2007

Presented capital-project proposals and progress reports at public meetings of an appointed transit board.

Governance learning and readiness

IICA Independent Directors’ Databank: Not yet registered

India's databank of independent directors, kept by the IICA, concerns people serving as independent directors of Indian companies. It plays no part in Canadian appointments, and I am not registered with it. Canadian boards assess independence and qualifications through their own processes and, for listed companies, the securities rules described on this page.

  • Quarterly board meetings at Halvery since 2019 as a presenter, and twice-yearly reports to its Audit and Risk Committee
  • Nine years on the Thornhaven Access Society board, including its finance committee and annual audit review
  • A university-based course on governance for not-for-profit directors, completed in 2018
  • Study of Canadian governance guidance for listed issuers, including Canada's national governance policy and its audit-committee rules, with Halvery's general counsel
  • Privacy impact assessment training taken alongside Halvery's product leaders in 2023