Remote Insurance Controller Jobs in Maryland (NOW HIRING)

For more than 30 years, The Squires Group (TSGi) has built its success on lasting relationships, exceptional service, and the people who make it all possible. As a WBENC-certified Woman-Owned Small Business and Workday Services Partner, we support federal, state, local, and commercial clients nationwide while fostering a culture where people are valued, ideas are welcomed, and contributions make a meaningful impact.

Our values-Integrity, Respect, Accountability, Collaboration, Excellence, and Giving Back-guide everything we do, from serving our clients to supporting one another.

As we continue our next phase of growth, we're seeking an experienced Controller to serve as our senior financial leader and trusted partner to the executive leadership team. This is more than an accounting role-it's an opportunity to influence business strategy, strengthen financial operations, ensure compliance, and help shape the future of the company.

We're looking for a leader who thrives at the intersection of strategy and execution. Whether you're partnering with executive leadership on long-term business planning, reviewing indirect rates, strengthening internal controls, or preparing for a DCAA audit, you'll move seamlessly between high-level strategy and operational detail while playing a critical role in our continued success.

You'll lead all aspects of accounting and finance, including financial reporting, budgeting, forecasting, cash management, payroll oversight, government contracting compliance, labor charging, timekeeping, audits, banking relationships, and strategic financial planning.

This position is primarily remote, with a preference for candidates located within reasonable driving distance of Annapolis, Maryland, to participate in occasional leadership meetings, collaborative planning sessions, and-yes-our legendary team events.

If you're looking for an opportunity where your expertise is valued, your voice is heard, and your work has a direct impact on a growing, relationship-driven organization, we'd love to meet you.

• Own and execute all accounting and finance operations, including GL, AP, AR, payroll, cash management, financial reporting, budgeting, forecasting, and close processes.
• Prepare and maintain accurate, timely financial statements, management reports, executive dashboards, forecasts, projections, cash flow reports, and ad hoc analyses.
• Manage the company's cash flow, banking relationships, lines of credit, liquidity planning, and related financial agreements.
• Serve as the internal subject matter expert for government contract accounting, DCAA compliance, FAR requirements, incurred cost submissions, audits, and cost accounting practices.
• Oversee timekeeping, labor charging, labor distribution, indirect cost management, and audit-ready documentation to ensure compliance with government contracting standards.
• Strengthen accounting policies, procedures, internal controls, systems, and reporting tools, including Deltek Costpoint and related platforms.
• Provide strategic financial guidance to executive leadership, including insights on performance, compliance risks, regulatory changes, and business planning.
• Lead, mentor, and develop accounting and finance staff while fostering accountability, collaboration, continuous improvement, and operational excellence.
• Coordinate with external partners, including auditors, tax advisors, banking institutions, payroll providers, insurance brokers, benefits vendors, legal counsel, and outside accounting firms.

• Bachelor's Degree in Accounting, Finance, or related field.
• Minimum of 15 years of progressive accounting and finance experience.
• Proven ability to operate independently as a senior hands-on accounting and finance leader in a small-to-mid-sized business environment
• Significant experience in government contracting environments.
• Deep understanding of DCAA regulations, FAR requirements, government contract accounting, and cost accounting principles.
• Expert-level experience with Deltek Costpoint.
• Proven experience managing monthly and annual financial close processes.
• Strong financial reporting, forecasting, budgeting, and cash management experience.
• Experience supporting DCAA audits, incurred cost submissions, and compliance reviews.
• Strong understanding of labor distribution, timekeeping compliance, and government contractor accounting requirements.
• Experience negotiating banking relationships, lines of credit, and vendor agreements.
• Excellent communication, ownership, judgement, and relationship management skills.
• Ability to work both strategically and operationally in a fast-paced environment.
• Flexibility to meet business needs typical of a senior leadership position.

Preferred Qualifications

• CPA strongly preferred.
• Experience scaling accounting operations in a growing small-to-mid-sized business.
• Experience supporting professional services, staffing, or government contracting organizations.
• Established network of industry relationships, including auditors, government contract accounting professionals, financial institutions, and compliance resources.
• Experience serving as a 401(k) Plan Administrator
• Experience partnering with Contracts and Human Resources to support contract administration, compliance, payroll, benefits, labor planning, and personnel-related financial operations.

Why Join TSGi?

• Work directly with executive leadership and influence company strategy.
• Play a critical role in shaping the financial future of a respected government services firm.
• Join a collaborative, entrepreneurial organization where your expertise and leadership make an immediate impact.
• Competitive compensation and benefits package.
• Remote flexibility with strong leadership visibility.

 The Squires Group is an Equal Opportunity Employer.

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