Rick Hennessey

About

Senior Product Manager with 10+ years turning complex operational workflows into B2B SaaS, mobile, compliance, and marketplace products. Most recently owned product delivery for Penske Fleet Insight Mobile across vehicle visibility, roadside assistance, maintenance workflows, analytics, and release execution. Known for roadmap ownership, customer escalation triage, quantified success metrics, API/data-flow literacy, and building clear requirements and acceptance criteria for field workflows.

Experience

• Product Manager, Fleet Insight Mobile · Penske Truck Leasing02-01-2026 – 06-30-2026

  ● Owned product definition and delivery for Fleet Insight Mobile, a B2B fleet app supporting vehicle visibility, roadside assistance, maintenance, invoices, insights, driver management, and rental workflows across iOS and Android. ● Prioritized roadmap scope, UX refinements, defects, and technical trade-offs across a 12-person team spanning iOS, Android, backend, QA, design, analytics, architecture, and product leadership. ● Redesigned high-stakes roadside-assistance workflows with validation, error states, permissions, review/edit behavior, trailer logic, attachments, and location capture; reduced key-flow steps by 30%+. ● Authored detailed requirements, user stories, and acceptance criteria for complex mobile workflows; triaged release issues, hotfix candidates, QA findings, and live-product behavior risks. ● Established GA4/Firebase measurement strategy; surfaced gaps between reported customer activity and actual logins and built a cleaner adoption, activation, engagement, and retention framework. ● Conducted JTBD interviews and behavioral analysis that identified product opportunities projected to lift monthly active usage by 80%; converted insights into roadmap recommendations.

• Founder & Head of Product · Paragon Heavy02-01-2023 – 02-28-2026

  ● Founded and led product for an AI-powered heavy-haul logistics platform spanning route planning, permit/compliance automation, GPS tracking, contracts, checkout, and payments. ● Designed a state-by-state compliance engine consolidating permit, weight-limit, route, and escort rules across 50 states into one workflow; cut route/permit research from ~8 hours to ~5 minutes per oversized load. ● Managed roadmap and execution for a 10-person team; translated carrier, dispatcher, pilot car, regulator, and operator needs into prioritized MVP features and technical requirements. ● Owned integration/product architecture decisions across maps, GPS/location data, compliance rules, contracts, and payments; partnered with engineering to diagnose workflow failures and validate feasibility.

• Product Manager / Product Strategist · WANDR09-01-2021 – 06-30-2023

  ● Led product strategy and UX for B2B SaaS and MVP builds, turning ambiguous operational and marketplace concepts into roadmaps, prototypes, user flows, and delivery-ready requirements. ● Product strategist for Asset Panda MVP rebuild, aligning asset-management workflows, UX, and technical implementation across product, design, and engineering. ● Product strategist for an AI-moderated AIA construction-document system and a car-sharing marketplace onboarding redesign, relevant to forms, compliance, document workflows, and activation.

• Product Manager · Hennessey Digital Consulting01-01-2020 – 11-30-2021

  ● Led product strategy and cross-functional execution for MVP/pilot products, including auto-quote, e-commerce, and 3D modeling/quote workflows for manufacturers. ● Translated complex business rules into user journeys, requirements, prototypes, and technical plans across executives, design, and engineering.

• Senior Digital Project Manager · Wood-Mode, LLC01-01-2014 – 01-31-2019

  ● Planned digital tools and customer-experience improvements for a 500+ dealer network; documented workflows and partnered with executives and dealer stakeholders on digital process improvements.

• Digital Experience Strategist · Stoner Bunting–

  Earlier experience: Digital Experience Strategist, Stoner Bunting; Digital Marketing Manager, Inovat. Client strategy, analytics, UX, prototyping, and multichannel digital programs.

• Digital Marketing Manager · Inovat–

  Earlier experience: Digital Experience Strategist, Stoner Bunting; Digital Marketing Manager, Inovat. Client strategy, analytics, UX, prototyping, and multichannel digital programs.

Education

• Stanford Graduate School of Business - Executive EducationExecutive Education, Executive Education
• ThinkfulFull Stack Engineering, Full Stack Engineering

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