Vice President 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!

About the Role

The Vice President of Sales will provide strategic leadership for the sales organization, driving revenue growth across our core solution areas: Managed IT, Print, Office Technology, and Security. You will build high-performing regional sales teams, develop and execute aggressive growth strategies, foster a client-first culture, and partner closely with executive leadership to achieve ambitious revenue targets while maintaining our reputation for world-class service.

This is a high-impact executive role for a proven sales leader who thrives in consultative B2B technology sales and wants to shape the future of a respected regional powerhouse.

Key Responsibilities

• Lead, mentor, and inspire a multi-state sales organization (including Directors, Managers, Account Executives, and Specialists) to exceed annual revenue and profitability goals
• Develop and implement comprehensive sales strategies, territory plans, and go-to-market approaches focused on new logo acquisition, account expansion, and cross-selling opportunities
• Drive consistent revenue growth across Managed IT Services, Managed Print, Unified Communications, and related solutions
• Collaborate with Marketing, Service Delivery, vCIO, and Solutions Engineering teams to align offerings with market needs and client feedback
• Identify emerging market opportunities, competitive trends, and innovative ways to expand our Northeast footprint
• Champion a high-performance, client-centric sales culture aligned with Usherwood’s family-owned values of integrity, teamwork, and exceptional service
• Report directly to executive leadership on sales performance, pipeline health, and strategic initiatives

Qualifications & Experience

• 10 years of progressive B2B sales leadership experience, with at least 5 years in a senior sales executive role (VP, Director, or equivalent)
• Proven track record of driving multi-million dollar revenue growth in technology services, office equipment, managed print, IT solutions, or related industries (copier/MFP dealer or technology reseller experience strongly preferred)
• Deep understanding of consultative/solution selling, managed services, recurring revenue models, and complex B2B sales cycles
• Experience leading distributed/regional sales teams across multiple states or territories
• Strong strategic thinking combined with hands-on leadership and coaching ability
• Excellent communication, negotiation, and presentation skills with C-level executives
• Proficiency with CRM systems (e.g., Salesforce), sales analytics tools, and modern sales methodologies
• Bachelor’s degree required; MBA or advanced degree a plus

What We Offer:

• Benefits: Comprehensive health, dental, and vision insurance, 401K with company match, paid time off, and much more.
• Unlimited PTO!!!
• Culture: Join a team that values growth, innovation, and world class service.
• 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!