Director, SaaS Sales

This is a fully remote position, open to applicants in Illinois.

📋 Description

• Carry and fulfill a personal annual sales quota, taking direct ownership of a pipeline that includes both new and expansion opportunities for ShipperGuide.

• Proactively seek out, develop, and finalize strategic deals while exemplifying top-tier selling practices for the team.

• Manage a personal portfolio of clients, which encompasses key accounts and high-value prospects, with complete responsibility for forecasting and maintaining pipeline health.

• Create and implement a cohesive go-to-market strategy for both ShipperGuide and OpenDock, aimed at maximizing market penetration and driving revenue growth.

• Oversee comprehensive sales execution across the funnel, from lead qualification to closing and onboarding processes.

• Establish repeatable sales procedures and ensure the consistent use of tools, CRM maintenance, and reporting standards.

• Collaborate with marketing to define and enhance Ideal Customer Profiles (ICPs), messaging, and campaign strategies.

• Coordinate with Customer Success to guarantee a seamless transition from sales to onboarding and retention efforts.

• Partner with Finance to develop pricing strategies, approve discounts, and conduct revenue forecasting.

• Work alongside the Account Management team to proactively identify and implement strategies for account growth, including upselling and cross-selling.

• Collaborate closely with Managed Transportation and Brokerage sales leadership to uncover cross-sell and upsell opportunities.

⛳️ Requirements

• Minimum of 7 years in SaaS TMS sales, with at least 5 years in a leadership capacity, including direct quota-carrying responsibilities at the Director level or higher.

• Experience in public speaking and participating in events.

• Demonstrated success in personally closing multi-million-dollar deals while also leading a team to surpass Annual Recurring Revenue (ARR) targets.

• Strong operational discipline with the capability to establish scalable and repeatable sales processes.

• Proven success in guiding teams to exceed multi-million-dollar ARR benchmarks.

• Exceptional skills in communication, negotiation, and presentation.

• Proficiency with Salesforce, SalesLoft, and sales analytics tools.

• Background in selling to supply chain, logistics, transportation, or related industries.

• Experience in managing multi-product sales teams or selling a platform with interconnected offerings.

• Familiarity with both SMB/mid-market and enterprise SaaS sales dynamics.

• Proven history of working closely with marketing and product teams to refine go-to-market strategies.

🏝️ Benefits

• Competitive base salaries – we are committed to rewarding top talent.

• Highly competitive equity package – become a shareholder in our company!

• Unlimited Loadie Time Off – PTO and sick days without a cap.

• Comprehensive Medical, Dental, and Vision insurance plans.

• 401k Match.