Job Description
Simplex Group is seeking an experienced Digital Product Manager to lead the discovery, strategy, and delivery of digital products that solve real customer problems and drive measurable business outcomes as part of our digital transformation.
This role is responsible for deeply understanding customer needs, business objectives, and technical constraints—and translating that understanding into a clear product vision and prioritized roadmap. The Digital Product Manager will focus on how products are designed, packaged, priced, delivered, and experienced by customers—including digital experiences through our portal and mobile app; while partnering closely with design, software engineering, marketing, sales, and operations.
The ideal candidate is outcome-driven, not feature-driven. You are comfortable making hard prioritization decisions, testing assumptions, and using data and customer insight to guide direction. You empower teams with clarity rather than control, and you measure success by customer impact and business results—not output alone.
As Simplex Group modernizes how its products and services are delivered through digital channels, this role will be critical in shaping experiences that customers trust, adopt, and rely on. We are looking for a product leader who embodies strong product thinking and can help elevate how product is practiced across the organization.
About Simplex Group
For over 25 years, Simplex Group has supported trucking companies and owner-operators with DOT/FMCSA compliance management, tax and permitting services, commercial insurance, and operational solutions.
Simplex Group believes in respect and fairness; prizes quality and reliability; and is driven by a can-do attitude. Our culture fosters a team-oriented working environment where ideas and initiatives from all corners of the company are welcome. We have a clear vision and a thirst for success, and we’re looking for team members who share our passion and drive.
Job Description & Responsibilities
The Digital Product Manager serves as the owner of Simplex Group’s digital product vision and execution, responsible for ensuring that our digital solutions solve real customer problems while delivering measurable business outcomes.
This role leads product discovery and delivery for Simplex Group’s customer-facing digital experiences—including the customer portal and mobile app—by deeply understanding customer needs, operational workflows, and business objectives.
The responsibilities of this position include:
● Define and execute the product vision and strategy for the Simplex customer portal and mobile app, aligned with company goals and customer needs
● Design and development of new products including their digital delivery and the user experience within the portal and mobile app
● Lead the end-to-end product lifecycle: discovery, requirements, design, development, QA, launch, and iteration
● Prioritize features and enhancements that drive engagement, self-service, and satisfaction for both new and existing customers
● Work closely with Operations and SMEs to convert service workflows into digital modules
● Develop expert-level understanding of the trucking industry including the customer personas, journeys and pain points through research, analytics, and direct customer feedback to create a differentiated product experience
● Collaborate closely with UX/UI designers to deliver seamless, modern, and accessible digital experiences
● Build strong feedback loops with sales and customer-facing teams to continuously refine products based on real-world input
● Stay ahead of industry and technology trends to identify new opportunities for innovation
● Ensure alignment between product, development, design, and operations on roadmap priorities and delivery milestones
● Define and refine the company’s product portfolio including value propositions, service levels, and pricing models by partnering with sales and finance
● Define, track, and report on product KPIs — including adoption, engagement, satisfaction, retention, revenue, and margin impact
● Collaborate with marketing to develop positioning and go-to-market materials for new or refined services
● Drive iterative improvements to UX, workflows, and automation to increase customer value
Qualifications
● 7+ years in Product Management, preferably with ownership of digital products
● Proven track record leading digital product strategy and delivery, including UI/UX design
● Experience in logistics, transportation, or a regulated industry strongly preferred
● Strategic thinker with strong operational and analytical skills
● Deep understanding of how to translate customer needs into offerings
● Exceptional communication and stakeholder management skills
● Data-driven decision-maker with strong business acumen and financial understanding
● A visionary who likes to create and push boundaries to create differentiation in the market
Compensation & Benefits
● Medical, Vision, and Dental: 100% Employer Paid (for Simplex Associate)
● PTO & Company Paid Holidays
● Employee Life Insurance
● 401k with Employer Match
● Job type: Full time (in-office)
● Location: Doral, FL (Not a remote position)