Account Executive

Brickwork GTM; Chesapeake (VA); On-site; USD 90,000 - 130,000; Full time

Job summary

Charles IT is seeking a highly driven Account Executive to accelerate growth within Financial Services and Alternative Investments. You will prospect, open new logos, and develop long-term relationships in a regulated environment, leveraging a strong network and targeted outbound strategies.

The role emphasizes self-sourcing, executive-level communication, and collaboration with security teams to craft compliant IT and MSSP solutions. On-site in Chesapeake, with local travel as needed.

Qualifications

• 5+ years of B2B sales experience with a hunter mindset.
• Experience selling to Financial Services or similar regulated sectors is preferred.
• Proven ability to source, nurture, and close new business.

Responsibilities

• Generate net-new business by prospecting and hunting for new logo opportunities.
• Build relationships with senior decision-makers (CIOs, CTOs, COOs, Compliance Leaders).
• Develop pipeline via outbound efforts, referrals, partnerships, and events.
• Manage inbound leads and convert to opportunities; conduct discovery and onsite assessments.
• Collaborate with internal teams to tailor MSSP, IT, and compliance-focused solutions.
• Maintain CRM activity, pipeline hygiene, and accurate forecasting.

Skills

Hunter mindset

New logo prospecting

B2B sales

Executive-level communication

Regulated environments

Tools

HubSpot CRM

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 are seeking a highly driven Hunter-style Account Executive to accelerate growth within the Financial Services market, with a strong focus on Alternative Investment firms. This role is designed for a proactive seller who thrives on building pipeline independently, opening new logos, and developing long-term relationships within a regulated, compliance-driven environment.

Approximately 20% of opportunities will be company-provided leads, while 80% of business development is expected to be generated through the Account Executive’s personal network, referrals, partnerships, and targeted outbound efforts.

Responsibilities

• Generate net-new business by prospecting and hunting for new logo opportunities within Financial Services and Alternative Investments
• Build and maintain relationships with senior decision-makers including CIOs, CTOs, COOs, and Compliance Leaders
• Develop pipeline through outbound outreach, networking, referrals, strategic partnerships, and industry events
• Manage and convert inbound leads into qualified opportunities
• Conduct discovery meetings and onsite assessments to understand technical, security, and compliance requirements
• Collaborate with internal technical and security teams to develop tailored MSSP, IT, and compliance-driven solutions
• Position offerings that address regulatory frameworks such as SEC, SOC 2, ISO 27001, and similar standards
• Maintain accurate CRM activity, pipeline hygiene, forecasting, and reporting
• Prepare proposals, contracts, and sales documentation and support clean handoffs post-close
• Represent Charles IT professionally within the Financial Services and Alternative Investment community

Requirements

• 5+ years of B2B sales experience with a strong hunter mindset
• Background selling into Financial Services; experience with Alternative Investment firms strongly preferred
• Experience selling managed services, MSSP offerings, or compliance-focused solutions
• Strong understanding of regulated environments and security/compliance requirements
• Proven ability to self-source, hunt, and close new business
• Excellent consultative selling, negotiation, and executive-level communication skills
• Highly organized with strong administrative and reporting discipline
• CRM experience required; HubSpot experience is a plus
• Ability to work from the Chesapeake office and travel locally as needed

Commitment to Inclusion

Charles IT offers a comprehensive benefits package including medical, dental, vision, life and disability insurance, paid holidays, PTO, 401(k), performance-based bonuses, professional development opportunities, and a collaborative, growth-oriented culture.

Charles IT is an equal opportunity employer committed to fostering an inclusive and respectful work environment. We welcome candidates from diverse backgrounds and experiences and do not discriminate based on any protected characteristic