Director of Sales

Usherwood Office Technology is a proud family-owned business with a rich legacy of delivering innovative office technology solutions, including managed IT services, print management, and cutting-edge office equipment. For decades, we have fostered a warm collaborative environment where our employees thrive, building meaningful relationships with teammates who share a passion for excellence and client success. At Usherwood, we are dedicated to empowering our clients and each other. With real opportunities for professional growth and career advancement, you'll work alongside supportive colleagues who make every day rewarding. 

Usherwood currently operates 19 offices throughout New England and New York, with ambitious growth plans set for 2026 and beyond. Join a company that's rapidly expanding and build your career with a true industry leader!

The Director of Sales is a strategic, hands‑on leader responsible for driving revenue, developing high‑performing teams, and shaping Usherwood’s go‑to‑market strategy. This role requires deep experience in office technology or related B2B solutions, a strong understanding of consultative selling, and the ability to inspire and coach a team to exceed targets. The on target earning for this role is $175,000.

Key Responsibilities

• Develop and execute a comprehensive sales strategy aligned with company growth goals
• Lead, mentor, and motivate a team of Account Executives and Sales Managers
• Build a strong pipeline through forecasting, territory planning, and performance management
• Strengthen customer relationships and expand market presence across key verticals
• Collaborate with marketing, operations, and service teams to ensure a seamless customer experience
• Analyze market trends, competitive activity, and emerging technologies to inform strategy
• Report on KPIs, revenue performance, and strategic initiatives to executive leadership

Qualifications

• 5+ years of progressive sales leadership experience, preferably in office technology, physical security systems, or IT business services
• Proven track record of leading teams to exceed revenue targets
• Strong understanding of solution selling and long‑cycle B2B sales
• Excellent communication, negotiation, and presentation skills
• Data‑driven mindset with the ability to translate insights into action
• High level of business acumen and strategic thinking

What We Offer:

• Benefits: Comprehensive health, dental, and vision insurance, 401K with company match, paid time off, and much more.
• 4 Weeks PTO your first year!
• Culture: Join a team that values growth, innovation, and world class service.
• Career Development: Excellent training where you’ll be working alongside industry experts and leaders committed to your success. 
• Continuing Education: Company paid training and certification opportunities 

Equal Opportunity Employer:

At Usherwood Office Technology, we are committed to fostering a diverse and inclusive workplace where everyone feels valued, respected, and empowered to succeed. We proudly provide Equal Employment opportunities to all individuals regardless of race, color, religion, sex, national origin, age, disability, veteran status, sexual orientation, gender identity, or any other characteristic protected by law. Our family-owned culture thrives on embracing unique perspectives and we strive to create an environment where every employee can grow, contribute, and belong. Join us in building a brighter, more inclusive future!