Director of Sales

About the Role

Gilmore is seeking a high-impact Director of Sales to build, lead, and execute a scalable sales engine that drives consistent, profitable revenue growth across our core service lines, including shredding, records management, commercial warehouse, and compliance solutions. This is a hands-on, player-coach leadership role responsible for both building the sales function and directly contributing to revenue. The ideal candidate is a proven builder who thrives in a performance-driven environment and is motivated by creating structure, accountability, and measurable results.

Responsibilities

• Own and achieve company revenue targets (monthly, quarterly, annual)
• Build and maintain a healthy pipeline (targeting 3-5x revenue coverage)
• Drive new customer acquisition across defined target markets
• Personally close high-value and strategic accounts
• Develop, implement, and continuously improve Gilmore's Proven Sales Process
• Establish and enforce CRM discipline using HubSpot
• Define pipeline stages, forecasting methodology, and reporting cadence
• Identify, prioritize, and resolve sales bottlenecks through structured problem-solving
• Recruit, hire, and develop Sales Development Representatives (SDRs) and future Territory Managers
• Lead weekly Sales Level 10 (L10) meetings
• Conduct consistent pipeline and performance reviews
• Coach and develop team members while holding them accountable to activity and results
• Define and prioritize target verticals, with a focus on recurring commercial customers
• Build and execute outbound strategies, including cold outreach, referral partnerships, and channel development
• Partner with marketing to drive lead generation and campaign effectiveness
• Support the launch and growth of new service offerings, including compliance-based solutions
• Ensure seamless handoff from Sales to Operations and Billing
• Partner with Finance on pricing strategy and deal profitability
• Collaborate with Operations to ensure service delivery meets customer expectations

Qualifications & Experience

• 5–10+ years of B2B sales experience, preferably in service-based industries
• Proven track record of generating pipeline and closing new business
• Experience building or scaling a sales function or team
• Strong leadership, coaching, and accountability skills
• Proficiency with CRM systems (HubSpot preferred)
• Familiarity with EOS (Entrepreneurial Operating System) is a plus
• Ability to operate effectively in a fast-paced, growth-oriented environment

Core Competencies

• Results-driven with a strong sense of ownership
• Process-oriented with the ability to build structure
• Effective communicator and team leader
• Strategic thinker with hands-on execution capability
• High level of integrity and professionalism

Performance Metrics

Success in this role will be measured by:

• Revenue growth
• Pipeline value and coverage
• New contracts won (volume and value)
• Close rate and average deal size
• Sales activity and pipeline conversion metrics
• Team performance and accountability

Compensation & Growth Opportunity

This role is designed for a high-impact sales leader who is motivated by building, winning, and being rewarded for results. Compensation includes a competitive base salary combined with an aggressive, performance-driven incentive structure tied directly to new revenue, pipeline creation, and overall sales growth. Total on-target earnings are expected to exceed $175k, with top performers having the opportunity to earn $200k+ as they scale the business. This is not a maintenance role - it is a build-and-grow opportunity. The right candidate will have the autonomy and support to create a scalable sales engine, make a measurable impact on company performance, and grow into broader leadership responsibility as Gilmore continues to expand.