Chief of Staff

Flexi Software

Chief of Staff supporting CEO in executing strategic priorities at Flexi Software. Collaborating across departments to drive growth and operational efficiency in enterprise software.

Posted 5/8/2026full-timeRemote • 🇺🇸 United StatesLead💰 $95,000 - $115,000 per yearWebsite

About the role

Key responsibilities & impact

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

What you’ll need

2+ years of experience in consulting, investing, strategy, operations, or similar analytical roles
Demonstrated experience supporting or working 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

Benefits

Comp & perks

Paid holidays and paid time off
401(k) Plan with company participation
Health and dental insurance
Life and disability insurance
Vision discount plan

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

project managementExcel modelingfinancial statementsdata analysisAI toolsoperational efficiencydashboard developmentreporting toolsbusiness reviewsstrategy development

Soft Skills

communication skillsorganizational skillsattention to detailsynthesis of complex issuesstructured recommendationscross-functional collaborationexecutive supportproblem-solvingadaptabilityleadership