VP of Sales

Logistics is broken. Let’s fix it.

We are a team of engineers, product designers, and customer champions applying the most transformative technology of our times, AI, to one of the largest industries in the world: logistics. Our mission is to streamline freight brokerage, carrier management, and 3PL operations through automation, freeing teams to focus on high-value strategic work.

We’re now looking for our first Vice President of Sales to scale our go-to-market engine and lead Augment’s next phase of growth.

• Build, train and lead a high-performing sales organization across enterprise and mid-market logistics.

• Design the GTM playbook including forecasting, enablement, and pipeline discipline from the ground up.

• Partner directly with Product and Engineering to translate customer insight into roadmap priorities.

• Personally drive and close strategic enterprise accounts in fleets, shippers, 3PLs and freight brokerages

• Represent Augment at major logistics events and with industry executives.

• 10+ years of B2B technology sales experience, with at least 5 years in logistics, transportation, or supply chain.

• Track record of owning $50M+ annual quotas and managing 25+ person sales organizations.

• Proven builder: You’ve scaled from founder-led sales to a structured, metrics-driven system.

• Skilled communicator who can translate AI and automation into clear ROI for operators.

• Hands-on, highly organized, detail-oriented, and comfortable leading both from the front and from the data.

• Hard-working, owner mentality. We are looking for leaders who can lean in and rapidly accelerate growth.

• Chicago-based or able to travel regularly to our Chicago hub.

• Competitive Salary + Stock Options

• Comprehensive Health, Vision, and Dental Benefits

• Flexible PTO

• On-site Gym

• Monthly stipend

At Augment, we set out to create a fully autonomous AI platform that streamlines operations and reclaims the human element in logistics. Our founders recognized a pattern: talented professionals were stuck handling manual data entry, phone calls, and repetitive tasks, instead of focusing on high-impact problem-solving and strategic decision-making.

That insight became our mission—to free logistics professionals from busywork so they can focus on what truly drives business growth. Augment isn’t just about efficiency; it’s about transforming an entire industry by empowering teams with AI-driven solutions that make logistics smarter, faster, and more adaptive.

Join us on this journey!

We are an equal-opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, gender identity, sexual orientation, age, marital status, veteran status, disability status, or any other legally protected status. Augment is committed to providing reasonable accommodations for candidates with disabilities through the hiring process.