Sales Director

Exceptional Service. Endless Improvement. Passionate People. Honest and Forthright. These values guide everything we do, and we achieve them thanks to the diverse and collaborative efforts of our team. We are dedicated to creating a supportive environment where every team member can thrive. This includes fostering learning, professional growth, and valuing each team member’s input, all within a culture that promotes work-life balance and a strong sense of belonging. As a Sales Director, you’ll take a consultative approach to driving new business and expanding Charles IT’s presence in highly regulated industries. You’ll focus on cultivating long-term relationships with key decision-makers, aligning their business goals with our trusted managed services. Your role will center on identifying new opportunities, representing our brand locally, and guiding prospects through a strategic, value-focused sales journey. Responsibilities Lead strategic, executive-level sales engagements with mid-market and enterprise clients. Develop tailored, value-focused solutions that align with each client’s business goals and regulatory needs (HIPAA, CMMC, SOC 2, etc.). Navigate complex buying cycles with multiple stakeholders, including C-suite leaders. Serve as a trusted advisor and long-term partner to key accounts, representing Charles IT with authority and insight. Prospect and close net new business while expanding relationships within major accounts. Represent Charles IT at high-level industry events and executive forums. Maintain precision in pipeline forecasting, client communication, and CRM hygiene (HubSpot). Requirements 10–12+ years of B2B sales experience, including a strong background in IT services, cybersecurity, or managed services. Executive-level presence with the ability to earn the trust of CFOs, CTOs, and business owners. Sophisticated consultative selling skills—able to listen deeply, think strategically, and advise credibly. Proven success closing multi-year, high-value deals in complex environments. High degree of self-direction, with the polish, pace, and discretion expected in a client-facing leadership role. A crisp, persuasive communicator—verbally and in writing. Located in or willing to travel regularly to Stamford or Middletown, CT. Benefits Charles IT offers a competitive benefits program including Medical, Dental, Vision, Life, Disability, Paid Holidays, PTO, 401K, and bonuses. In addition, we offer free dry cleaning, a fully stocked break room, Friday team lunches, paid training, team-building outings every quarter, professional development and so much more!  Our Commitment to Inclusion:  Charles IT is committed to creating an inclusive environment for all employees. We do not discriminate based on race, color, religion, sex, age, national origin, marital status, disability, veteran status, genetic information, sexual orientation, gender identity, or any other protected category. We welcome and encourage diverse perspectives.  The information contained in this job description is for compliance with the American with Disabilities Act (A.D.A.) and is not an exhaustive list of the duties performed for this position. Additional duties may be required.  If you’re excited about contributing your expertise to a fast-growing company that values innovation and teamwork, we’d love to hear from you!