Fleetworthy Customer Portal
Product Manager (Group / Senior equivalent)
Led product strategy and roadmap across three flagship products — Bestpass tolling, ExpressTruckTax, and the Fleetworthy flagship portal — and drove the new customer portal from ideation to launch.
Context & problem
Bestpass (now Fleetworthy) consolidates tolls, compliance, safety, and tax for trucking fleets. Through acquisition it ended up with multiple products and a dated customer experience.
I led product across three flagship products at once, and owned the build of a new, modernized version of the Bestpass customer portal — plus the company's first fully self-serve onboarding flow.
Fleets don't just pay tolls; they manage which transponder — the in-cab device that's read at toll plazas — belongs to which truck as vehicles are retired and replaced. The portal had to make that real-world operational workflow simple, and surface where it was breaking down.
We served two very different customers in one product — large enterprise fleets and independent owner-operators — each with distinct needs, workflows, and expectations to balance.
What I did
- Led product strategy and roadmap across three flagship products simultaneously — Bestpass tolling, ExpressTruckTax (acquisition), and the Fleetworthy flagship portal (acquisition).
- Led the new version of the Bestpass customer portal from ideation to launch, modernizing the tech stack along the way.
- Launched the company's first fully self-serve onboarding flow with payments — letting new customers sign up, configure their account, and pay without a sales hand-off or manual back-office setup, which boosted signups and earned a 92% “very easy to use” rating.
- Redesigned reporting from real customer evidence — interviewed users on which legacy reports they relied on and why, then decided what to retire, what to highlight, and what new reports to build, including ones that surfaced costly gaps like transponders assigned but not tracking data and trucks racking up plate (toll-by-plate) charges because no transponder was assigned.
- Designed transponder-management workflows — e.g. moving a transponder from a retired truck to a newly purchased one — so fleets could keep device-to-vehicle assignments accurate in our system.
- Optimized the mobile experience for owner-operators managing their fleet on the go, not just from a desk.
- Knocked out high-impact, low-hanging fruit — fixing login issues and session timeouts that were quietly hurting the everyday experience.
- Wrote 50+ SQL scripts for data pulls and dashboards, partnering with the data team to monitor and improve adoption and success metrics.
- Mentored and developed PMs — trained a product analyst into a PM — and influenced other PMs' roadmaps to drive alignment across the portfolio.
Outcome & impact
- Reduced support tickets by 60% on top issues and improved CSAT with the new portal.
- Boosted signups with self-serve onboarding, earning a 92% “very easy to use” rating from users.
- Contributed to company growth from $150M to $850M, partnering with execs to align products across the portfolio.
A look inside
Selected screens from the product.
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