From the night desk to the product roadmap

Mandate

Make the product dependable and fairly priced for carriers of one to twenty-five trucks while the company grew past ten thousand accounts.

Outcomes

• Made fee-free broker terms the payment default and priced advances in dollars
• Introduced hours-shortfall flags on load offers for connected fleets
• Limited location sharing to the load window and declined a partner's wider request
• Grew paying carrier accounts from about 7,600 to 12,400

Decisions in context

The chief product officer role at Ostervane joins three things that small carriers experience as one: the work of moving a load, the cost of getting paid for it, and the data the app collects on the way. I report to Ruth Lomenzo and lead five directors across load and dispatch, documents, payments, design and research. I do not run engineering, credit decisions or the partner bank's programme, but I am accountable for what carriers see and what they pay. My time goes mostly into decisions where revenue and a carrier's interest point in different directions, and into making those trade-offs visible to our board. Each decision described on my Impact page was taken in this role. I also built a practice of quarterly support shifts for every product leader, so that complaints reach us in carriers' own words before they become churn.

Reason for the move

Current appointment; pursuing a first independent board seat alongside it.

Mandate

Turn a founder-built load and invoicing app into a product a four-truck owner could run the business from.

Outcomes

• Built offline document capture with a visible upload queue
• Moved subscription pricing from seats to trucks, with free dispatcher seats
• Grew paying carriers from about 3,100 to 7,600

Decisions in context

When I arrived, Ostervane's founders had a loyal following among owner-operators and a product that worked well in town and badly on the road. Invoices failed silently in dead zones, and carriers discovered missing paperwork only when a broker refused to pay. My first year went into offline capture: documents stored on the phone, a visible queue and a clear message when a page had reached the broker. I then changed pricing from seats to trucks, after watching families share one login because a second seat cost money. Revenue per account fell slightly in the first year and rose as fleets grew. I built a research team of four and a habit of testing in truck stops. The pandemic years tested everything, as freight rates swung and many new one-truck carriers joined with little office experience and urgent cash needs.

Reason for the move

Appointed chief product officer as the company's board added payments and data oversight to the product remit.

Mandate

Design the driver-facing logging application as customers moved from paper logs to electronic logging devices.

Outcomes

• Redesigned duty-status and remaining-hours screens with drivers
• Introduced driver-visible records of edits proposed by carriers
• Cut support calls per thousand drivers by about a third

Decisions in context

Tallowrun put me at the point where regulation, software and a driver's working day meet. Most of its customers were moving from paper logs to electronic logging devices, and drivers were understandably wary of a device recording every hour. My team designed the screens for changing duty status, reviewing remaining hours and accepting or rejecting edits proposed by the office. We made every proposed change visible to the driver before it applied, because a log altered without the driver's knowledge destroys trust in the whole system. I learnt to work with compliance specialists without turning product decisions into legal opinions, and to treat location records with care. The role grew from one product to a group of three. I left because I wanted to build for the smallest carriers, whose needs most fleet software treats as an afterthought.

Reason for the move

Joined Ostervane to work for small carriers rather than fleets of several hundred trucks.

Mandate

Improve the driver pay card and the fuel-card controls used by fleet managers.

Outcomes

• Replaced a monthly paper fee summary with fees shown on each transaction
• Added fleet-set fuel-card limits by location and time
• Reduced card disputes per thousand accounts by about a quarter

Decisions in context

Velmarsh hired me in the middle of the financial crisis, when fleets watched every dollar and drivers were suspicious of any card that carried fees. I managed the driver pay card, which carriers used to pay wages and trip advances. Fees for withdrawals and balance enquiries were disclosed, but drivers saw them only in a monthly statement. I worked with compliance and our bank's card team to show each fee on the transaction itself, which reduced revenue a little and complaints considerably. I also added fuel-card controls that let fleet managers limit purchases by location and time. Payments taught me the difference between a fee that is legal and a fee that a customer understands, and the value of reading dispute logs before writing requirements. I left to work on a product drivers used every hour, not once a week.

Reason for the move

Moved to telematics to work on software drivers used throughout the day.

Mandate

Install and configure dispatch and billing software at carriers with fifty to five hundred trucks.

Outcomes

• Completed implementations at more than forty carrier terminals
• Wrote the first written requirements from observed yard and night-desk work
• Simplified the driver settlement screen used by payroll clerks

Decisions in context

Carrowbrook took me from one carrier's dispatch office to dozens of them. I configured rating, dispatch and billing, trained office staff and stayed through each go-live week, often on the night shift. Mostly I saw that software designed in a conference room rarely survived a night shift. A screen that suited the controller could take a night dispatcher three times as long. I began keeping notes on what I watched people do, and in 2007 the director of product asked me to turn those notes into requirements. As a product analyst, I worked on driver settlements and billing exceptions, where small errors meant late or wrong pay. The role taught me to separate the person buying software from the people using it, and to give the second group more weight than they usually receive in a sales cycle.

Reason for the move

Joined a payments company to learn how fees and money movement shaped carriers' choices.

Mandate

Plan loads and drivers, reconcile paper logs and keep brokers and receivers informed.

Outcomes

• Kept a daily reconciliation of planned loads against logged hours
• Set up a night-desk handover sheet still in use when I left
• Tracked fuel-advance costs for leased owner-operators at their request

Decisions in context

I joined Wendcastle a month after graduating, expecting to plan routes and finding that the work was mostly about people's hours. Flatbed loads meant mills, lumber yards and construction sites, with long waits, tarping and receivers who closed early. My manager made me check every driver's log before promising a delivery time, and I learnt to say no to a broker when the hours were not there. By 2004 I led the night desk. Owner-operators leased to us asked me to track what their fuel advances had cost, because the deductions appeared on settlement statements without a running total. Those conversations shaped the payment rules I set two decades later. I left because our dispatch software made every task harder at night, and I wanted to understand why software for trucking seemed to be designed by people who had never sat at the desk.

Reason for the move

Moved into software after seeing how much of dispatch depended on tools built for someone else.