Chief of Staff

Description:

Flexi Software is seeking a Chief of Staff to support our CEO in accelerating the company’s strategic priorities and operational excellence during a critical period of modernization and growth. The Chief of Staff will work closely with the CEO to ensure strategic priorities are executed with clarity, speed, and precision, with the broader goal of scaling Flexi’s operations, driving sustainable growth, and unlocking long-term enterprise value. This individual will serve as a force multiplier to the CEO, connecting high-level strategy with day-to-day execution.

This role is ideal for someone who thrives in a dynamic environment, brings strong judgment and ownership, and is excited about working in enterprise software. The Chief of Staff will not be a passive participant. This person will be deeply embedded in both the strategic and tactical heartbeat of Flexi, with access to high-level decision making and the opportunity to shape the future of a long-standing and respected company.

The Chief of Staff is expected to travel frequently (6–10 times a year) to visit customers, attend industry events, visit other team members, and work in-person with the CEO as needed. This is a remote-eligible role, with a preference for candidates based in or near Atlanta, GA.

A B O U T F L E X I

Flexi Software has been a trusted provider of accounting solutions for over 30 years, offering both cloudbased and on-premise software tailored for organizations with complex accounting requirements, such as multi-entity and intercompany accounting. Our comprehensive suite includes modules like General Ledger, Accounts Payable, Accounts Receivable, Purchasing, Fixed Asset Management, Project Accounting, Workflow Automation, Financial Reporting, and Budget Software. Serving industries including banking, insurance, financial services, credit unions, healthcare, and business process outsourcing, Flexi is renowned for its robust features, flexible deployment options, and exceptional customer support.

In January 2025, Flexi was acquired by Quality Standard, a permanent capital holding company that acquires and grows fintech and govtech software businesses with a long-term ownership mindset. Quality Standard is actively investing in Flexi’s people, product, and operations. Flexi’s offices are located in Shelton, CT and Atlanta, GA. Quality Standard is headquartered in New York, NY.

R O L E S A N D R E S P O N S I B I L I T I E S

• Serve as right-hand to CEO, managing execution of the CEO’s top priorities, ensuring alignment, progress, and accountability
• Act as a thought partner and sounding board to the CEO and broader executive leadership team
• Drive key cross-functional initiatives across all departments: sales, marketing, engineering, product, business operations, finance, professional services, and support
• Identify and drive the adoption of AI tools and workflows to improve operational efficiency, accelerate execution, and help scale the business
• Identify gaps in existing systems or processes, and create and implement solutions to fill those gaps
• Support planning cycles (monthly, quarterly, annual), including goal setting, business reviews, and strategy development
• Prepare briefing materials, presentations, and follow-ups for internal and external meetings
• Develop internal dashboards, operating rhythms, and reporting tools to support decision-making, including the Flexi Scorecard – a snapshot of the most important metrics by which we hold ourselves accountable
• Step into gaps across the organization and thrive in high-need areas, delivering value wherever plugged in

Requirements:

• 2+ years of experience in consulting, investing, strategy, operations, or similar analytical roles
• Demonstrated experience supporting or workin g alongside senior executives
• Strong project management, organizational, and communication skills, with high attention to detail
• Ability to synthesize complex issues, develop structured recommendations, and drive execution
• Comfort with financial statements, metrics, and Excel modeling
• Experience in enterprise software, B2B SaaS, or technology-enabled services is a plus

P E R S O N A L C H A R A C T E R I S T I C S

• Proactive, self-directed, and capable of owning workstreams end-to-end
• Comfortable with ambiguity, fast decision-making, and a high bar for excellence
• High integrity, sound judgment, and trusted with confidential information
• Genuine curiosity about AI and emerging technologies; comfortable experimenting with and incorporating AI tools to improve personal productivity and team decision-making
• Collaborative and low ego; thrives on enabling others to succeed
• Curious, pragmatic, and eager to improve the business in small and big ways
• Positive attitude and sense of humor — work is way more fun with people you enjoy

Salary range for this positions is $95-115K/year with bonus eligibility. Additionally, Flexi provides excellent benefits including paid holidays and paid time off, a 401(k) Plan with company participation, health and dental insurance, life and disability insurance, and a vision discount plan.

Location: Remote-Eligible • Preference for Atlanta, GA

Only candidates under consideration will be contacted. Any offer of employment will be contingent upon positive criminal background check. No phone calls, please. Principals Only.

Drug-free workplace. M/F/V/H EEO