Regional Sales Executive

CaseGuard · Arlington · Remote

Posted 2/18/2026 · last confirmed live 8/26/2026

CaseGuard is a fast-growing startup based in the DC area, helping organizations securely redact sensitive information. We are looking for a driven, consultative Account Executive to own and grow a territory across multiple industries, including law enforcement, government, legal, healthcare, education, and enterprise organizations. This is an opportunity for someone who thrives in a high-growth startup environment, enjoys building relationships, and is energized by solving customer challenges and closing complex deals. You’ll have the autonomy to build out your territory while partnering closely with leadership, product, and customer-facing teams to help shape the future of CaseGuard. Responsibilities Own and grow a defined territory by developing and executing strategic sales plans across target industries. Manage the full sales cycle from prospecting to close, including outbound outreach, qualification, discovery, product demonstrations, proposal creation, negotiation, and contract execution. Generate new business opportunities through cold outreach, networking, referrals, and industry events. Build and maintain a strong pipeline through proactive prospecting and account development activities. Develop trusted relationships with key stakeholders and decision-makers across public and private sector organizations. Serve as a consultative advisor by understanding customer workflows, operational challenges, and compliance needs. Collaborate cross-functionally with Account Management, Product, Marketing, and Technical support team to deliver exceptional customer experiences. Maintain accurate pipeline activity, forecasting, and customer data within the CRM system. Represent CaseGuard at conferences, trade shows, and customer meetings across industries. Stay informed on industry trends, competitive offerings, and evolving customer needs within your territory. Qualifications: 3-5+ years of quota-carrying B2B software sales experience. Proven track record of consistently meeting and exceeding revenue targets. Experience managing complex, full-cycle sales processes. Strong prospecting, pipeline generation, and outbound sales skills. Experience owning a geographic territory. Excellent communication, presentation, negotiation, and relationship-building skills. Ability to work independently and thrive in a past-faced startup environment. Strong organizational and time management skills. Experience selling into the public sector, government, law enforcement, legal, healthcare, or education markets is highly preferred. Familiarity with CRM platforms and maintaining accurate forecasting and pipeline reporting. Willingness to travel for conferences, customer meetings, and industry events as needed. What Success Looks Like: Consistently achieving or exceeding quarterly and annual revenue goals. Building and maintaining a healthy, predictable sales pipeline. Expanding CaseGuard’s market presence and brand visibility within your territory. Developing long-term customer relationships and high customer satisfaction. Becoming a trusted advisor to organizations responsible for handling sensitive information. Benefits: Competitive Salary Stock Option Medical, Dental, and Vision Insurance 401K Paid Vacation Ten paid holidays per year Friendly and Learning environment Ability to commute/work hybrid: Arlington, VA, or remote Pay Range:  Base: $70,000 - $85,000 plus uncapped commission  OTE: $140,000 - $180,000+ About CaseGuard CaseGuard is a software company that helps law enforcement agencies, federal agencies, hospitals, schools, airports and others manage all their media redaction needs in one easy to use redaction software. CaseGuard Studio is one of its kind. Our team is driven by a passion for great software design, the creation of great products and the creative process, CaseGuard implements innovative ideas across multiple services and agencies. We invest in people. We nurture skills that are consistent with both our values and our future strategy. Our passionate pursuit of excellence, the application of our creativity to solve our clients’ challenges, our technical expertise and our collaborative spirit are measures of our success.

This role is published by CaseGuard on greenhouse. SwiftFit is not the employer and does not accept applications.