Jobs at FleetWorks

Own the vision, strategy, roadmap, and execution of FleetWorks’ AI-powered freight marketplace products for brokers and carriers. Partner with founders, engineering, operations, and go-to-market teams to scale adoption, establish product excellence, ship rapidly, and drive measurable outcomes. The role requires strong customer instincts, data fluency, systems thinking, comfort with ambiguity, and a founder-like ownership mindset.

Own the vision, strategy, roadmap, and end-to-end execution for AI-powered marketplace products serving freight brokers and carriers. Partner with founders, engineering, operations, and go-to-market teams to scale adoption, ship quickly, establish product standards, and deliver measurable results. Use customer insights and data to make high-judgment decisions, manage change, and build category-defining products in an ambiguous, fast-paced environment.

The Senior Software Engineer will work directly with customers to develop and integrate AI-driven solutions, ensuring operational success and feature deployment in real-world environments.

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As a Senior Software Engineer at FleetWorks, you will lead customer integrations, build workflows, develop platform components, and provide field insights to enhance software solutions in freight booking.

Lead technical delivery for customer implementations and integrations, architect and build workflows and platform components, adapt solutions to messy real-world customer systems, shape product roadmap with field insights, and travel 20–30% while working from the Chicago office.

As a Senior Software Engineer, you'll lead customer implementations, build workflows, develop platform components, and provide insights from the field, all while traveling to customer sites.

As a Senior Software Engineer, you will lead end-to-end feature development for a customer-facing product, make product decisions, and collaborate with team members and users.

As a Senior Product Engineer, you will own end-to-end feature development on customer-facing products, make product decisions, and work closely with a collaborative team.