Sr. Manager of Transportation & Gig Network Planning

Reporting to the CEO, this leadership role is preferred to be based in Cincinnati, but other metro applicants will be considered and are encouraged to apply.

We are seeking a strategic and analytical leader to serve as our Sr. Manager of Transportation & Gig Network Planning. This role will own the planning and performance of our driver and carrier network — ensuring capacity aligns with market demand, identifying operational bottlenecks, and implementing solutions that drive efficiency and responsiveness across our platform.

You will be responsible for ensuring our network is not only scalable and compliant, but also high-performing and deeply engaged. Ideal candidates will bring proven experience developing gig or carrier-based logistics networks, with a track record of using data to forecast needs, diagnose underperformance, and take corrective action. Your leadership will play a critical role in strengthening market readiness, fostering a reliable and motivated driver base, and optimizing network health across all stages — from onboarding and compliance to long-term engagement and retention.

Responsibilities – What you will do

· Scale Network Growth – Own and drive the strategy for driver and carrier network growth, forecast demand coverage, and overall market readiness.

· Own Active Network Capacity – Identify capacity constraints, unlock efficiencies, and optimize onboarding.

· Drive Continuous Improvement – Use data to identify cost drivers, fulfillment bottlenecks, and opportunities for redesign.

· Champion New Network Products – Co-lead with the Product Director new driver/carrier pilot programs and product rollouts to enhance engagement and performance.

· Design and Pioneer our Fleet Network – Oversee our Driver team’s mission to build out an STL/LTL/FTL network to pioneer our large asset capacity offering, recruiting owner-operators and fleet owners.

· Lead our Driver/Logistics Services & Compliance teams – develop a high-performing team, fostering a culture of accountability, development, and results.

· Oversee Driver Regulations and Insurance – Oversee driver and carrier compliance with all regulatory and insurance requirements, champion our insurance coverage renewals, and look for gaps and cost savings.

What makes you an extra great fit:

· You’re a systems thinker – You see the full picture of how revenue opportunities, gig/carrier networks, and operations connect—and design accordingly.

· You’re data-driven and execution-oriented – You ground your strategy in data, move quickly from analysis to action, and can lead execution across teams.

· You thrive in ambiguity – You’re energized by complexity and enjoy building new strategies and models in uncharted territory.

· You’re comfortable in a fast-paced, scaling startup environment and energized by complex operational challenges.

· You have 10+ years of relevant experience – You’ve worked with a logistics or gig network, transportation, operations strategy, supply chain consulting, or a fast-paced tech environment. Experience with SQL, Looker, network modeling tools, or transportation systems is a strong plus.

What We Value / Our Culture Pillars

· Ownership – We are stakeholders, freely operating within a framework of accountability, expecting more from ourselves and others while bringing solutions, not problems.

· Transparency – We’re forthright in our capabilities, sharing what we know and learning through every circumstance while leading with authenticity.

· Relentless innovation – We are designing for tomorrow, not settling for industry standards, but taking calculated risks while reaching for excellence.

· Discipline – We recruit disciplined people who apply disciplined thought to execute disciplined action. Discipline outweighs motivation.

Benefits

· Competitive salary and performance-based bonus

· Equity opportunity in a growing, venture-backed company

· Comprehensive health, dental, and vision insurance

· 401(k) account

· Generous PTO and parental leave

· Hybrid-flex work culture with regular team meetups

· The chance to shape the future of logistics in a driver-first marketplace