Head of Sales

Head of Sales

Job Type: Full-Time

Location: Remote – US

Compensation: $175K – $200K + Bonus + Equity

Role Overview

Seeking a highly hands-on Head of Sales to help scale and operationalize the enterprise sales organization during a critical phase of growth. This role requires a deeply experienced sales leader who thrives in the trenches—coaching reps, reviewing calls, improving outbound execution, advancing strategic deals, and building a high-performance sales culture.

Must-Have Qualifications

• B2B SaaS experience — 5–15+ years, including significant experience leading and coaching enterprise Account Executives.
• Scaling expertise — Proven track record helping scale sales organizations in high-growth SaaS environments.
• Enterprise sales — Strong background in complex, consultative, multi-stakeholder deals.
• Outbound expertise — Deep understanding of outbound prospecting, account-based selling, and field/event-driven pipeline generation.
• Hands-on leadership — Passion for coaching, call review, and deal development.
• Forecasting discipline — Experience managing forecasting, pipeline inspection, and sales process discipline.
• Sales technology — Strong working knowledge of HubSpot, Gong/Jiminny, LinkedIn Sales Navigator, sequencing tools, and ABM platforms.
• Collaboration skills — Excellent communication, organizational, and cross-functional collaboration abilities.
• Travel readiness — Willingness to travel (~25%) for customer meetings, conferences, and team collaboration.

Helpful, But Not Required

• Field sales verticals — Selling into distributors, manufacturers, or industrial sectors.
• Hybrid sales environments — Experience in hybrid field/inside sales organizations.
• Scaling ARR — Experience scaling organizations from ~$10M to $35M+ ARR.
• Location preference — Raleigh or NYC-based preferred.

Key Responsibilities

Sales Leadership & Coaching

• Manage AEs — Directly manage and coach Account Executives focused on mid-market and enterprise sales.
• Pipeline reviews — Conduct regular 1:1s, forecast calls, and deal strategy sessions.
• Call reviews — Review recorded sales calls/demos to improve discovery, positioning, objection handling, and execution.
• Hands-on coaching — Provide coaching across the full sales cycle: prospecting, discovery, demos, pricing, procurement, and negotiation.
• Best practices — Reinforce pipeline management, account planning, forecasting, and CRM hygiene.
• Multi-threading — Help reps navigate complex buying committees.

ABM & Pipeline Development

• Account-based sales — Partner with Marketing and RevOps to operationalize account-based sales.
• Outbound strategies — Coach reps on personalized outbound tactics (emails, direct mail, executive outreach, video messaging).
• Workflow standards — Build scalable outbound workflows and prospecting standards.
• Conference support — Maximize pipeline generation before, during, and after events.
• Territory planning — Collaborate on account ownership models and vertical segmentation.

Deal Support & Enterprise Sales Execution

• Strategic deals — Join customer/prospect meetings to accelerate complex opportunities.

Forecasting & Operational Management

• Forecast discipline — Own forecasting and pipeline inspection processes.
• Accuracy improvement — Improve forecast accuracy, deal stage consistency, and close-date integrity.
• Rep accountability — Ensure activity standards, follow-up execution, and opportunity management.
• Operational management — Oversee PTO approvals, commission reviews, territory disputes, and performance management.
• RevOps partnership — Ensure adoption of HubSpot workflows, reporting, and sales processes.

About the Organization

A fast-growing SaaS company on a mission to transform field sales teams across industries such as manufacturing, automotive, packaging, and supplies. The platform enables outside sales reps to drive more revenue through modern sales enablement capabilities. With rapid growth, strong retention rates, and recent capital raises, the organization is scaling responsibly to support its next phase of expansion. The team is fully remote and global, with a collaborative culture strengthened by semi-annual onsite weeks and regular virtual/in-person events.