Head of Revenue

Grid-Line Transportation is seeking a Head of Revenue to build and own the company’s entire revenue engine. This role is responsible for designing, implementing, and enforcing the sales strategy, CRM architecture, sales playbooks, and performance culture that will allow the company to scale 10× over the next five years. This is a builder role, not a passive manager. The Head of Revenue will work hands-on with sales leadership, sales reps, and marketing to create structure, accountability, and predictable growth. Core Responsibilities Sales Strategy & ICP Ownership Define and document the Ideal Customer Profile (ICP), including: Target customer types Freight profiles (flatbed, steel, specialized) Lane strategy Margin thresholds Disqualifying criteria Establish clear revenue priorities and focus areas Align pricing, qualification, and deal selection with company goals CRM Ownership & Architecture Own CRM setup, structure, and governance Define pipeline stages, required fields, and data standards Build dashboards for: Pipeline health Activity metrics Conversion rates Rep performance Enforce CRM discipline (if it’s not in the CRM, it doesn’t exist) Sales Playbooks & Process Build and maintain a living sales playbook, including: Prospecting cadence Call and email frameworks Qualification standards Objection handling Pricing logic Sales-to-Operations handoff Train sales team on playbooks Audit execution and update playbooks quarterly Sales Team Leadership & Culture Lead and develop the Sales Manager and Sales Reps Establish a high-urgency, execution-driven sales culture Run weekly pipeline and performance reviews Set clear expectations and hold the team accountable to standards Drive consistency, focus, and follow-through Sales & Marketing Alignment Partner with Marketing to guide demand capture strategy, including: City- and lane-specific landing pages SEO keyword priorities (e.g., “Flatbed trucking Gary IN”) Messaging based on real sales conversations Provide continuous feedback from the sales floor to marketing Ensure marketing efforts directly support revenue goals Key Success Metrics CRM adoption and data accuracy Pipeline quality and predictability Sales rep productivity and execution Revenue growth and margin quality Sales process consistency and discipline Ideal Background 7–12+ years in B2B sales leadership Experience in logistics, trucking, freight, or asset-based services strongly preferred Proven experience building sales systems from the ground up Strong CRM experience (HubSpot, Salesforce, or similar) Comfortable enforcing standards and driving accountability Strategic thinker who is also operational and hands-on At Grid-Line, we move with purpose. We’re building a tech-powered operation designed for speed, efficiency, and excellence. If you thrive in a structured, high-accountability environment where your precision directly impacts compliance and safety, we want you on our team. Job Type: Full-time Pay: $100,000.00 - $115,000.00 per year Benefits: 401(k) 401(k) matching Dental insurance Health insurance Paid time off Prescription drug insurance Application Question(s): Are you able to work onsite? Experience: B2B Sales Leadership: 7 years (Required) logistics, trucking or freight: 3 years (Required) Ability to Commute: Dyer, IN 46311 (Required) Work Location: In person