Director of Sales

Company Overview Gilmore is a leading provider of confidential material destruction, commercial warehousing, and records management solutions. With a strong commitment to security, efficiency, and customer satisfaction, we pride ourselves on delivering on our corporate promise of people-centered security. Our family owned and operated organization specializes in offering comprehensive services to businesses across the southeastern United States and beyond. We encourage you to learn more about our services by visiting our website. Job Summary 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. Key Responsibilities Revenue & Pipeline Ownership 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 Sales Process & Execution 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 Team Leadership & Development 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 Go-To-Market Strategy 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 Cross-Functional Collaboration 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 Performance Metrics 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 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 Benefits Competitive salary commensurate with experience Comprehensive benefits package that includes health, dental, and vision insurance with a portion of premiums being covered by Gilmore Retirement savings plan with employer match Paid time off in accordance with company policy Dynamic and collaborative work environment focused on innovation and excellence 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. Director of Sales Gilmore Jacob Gilmore 31 East Fairfield Drive Pensacola FL 32501 View phone number on click.appcast.io Send Email Visit Website #J-18808-Ljbffr