Account Executive

Company: Charles IT
Location: Chesapeake
Posted on: February 16, 2026

Job Description:

Job Description Job Description Exceptional Service, Endless Improvement, Passionate People, and Honest and Forthright. Guided by our values, we foster a culture of growth, balance, and belonging where every team member can thrive We're seeking a highly motivated Account Executive to support our continued growth through proactive client outreach and strategic relationship development. This role requires a strong ability to identify new business opportunities, engage prospects with confidence, and deliver tailored solutions. The ideal candidate is goal-driven, persuasive, and thrives in a fast-paced, results-oriented environment. Responsibilities: Develop and manage relationships with senior executives and key decision-makers across mid-market organizations Identify and pursue high-value opportunities with longer sales cycles and complex business needs Conduct strategic outreach through cold calling, referrals, and networking to build a strong center of influence within the assigned territory Lead discovery meetings, onsite evaluations, and business reviews to assess client environments and deliver tailored IT solutions Collaborate with Technical Solutions Architects, vCIOs, and internal teams to design and present service offerings that address compliance (HIPAA, CMMC, SOC 2) and strategic objectives Represent Charles IT at industry events, roundtables, and networking functions to elevate brand visibility and foster key relationships Maintain accurate pipeline forecasting, account planning, and activity tracking in HubSpot CRM Requirements 3-5 years of B2B sales experience, with a strong background in IT solutions, MSPs, or professional services. Proven track record managing major or strategic accounts. Demonstrated experience selling to the C-suite, including CFOs, CTOs, and CISOs. Exceptional consultative selling, negotiation, and solution design skills. Familiarity with navigating RFPs, procurement, and legal/compliance processes. Entrepreneurial mindset and a proactive approach to identifying new opportunities. Willingness to travel as needed. HubSpot or comparable CRM experience required. Benefits Charles IT offers a comprehensive benefits package, including medical, dental, vision, life and disability insurance, paid holidays, PTO, 401(k), and performance-based bonuses. Team members also enjoy ongoing training, professional development, quarterly team-building events, and a collaborative workplace culture. Commitment to Inclusion: Charles IT is an equal opportunity employer committed to fostering an inclusive and respectful work environment. We welcome diverse backgrounds and perspectives and do not discriminate based on any protected characteristic.

Keywords: Charles IT, Chesapeake , Account Executive, Sales , Chesapeake, Virginia