The Chief of Staff will drive strategic initiatives, support executive leadership, manage key operations, and facilitate communication across the organization, ensuring alignment with company objectives.
About the Role
Engageware is seeking a high-impact Chief of Staff to serve as a force multiplier for our executive leadership team. Reporting directly to the CFO — and working in close partnership with the CEO and other senior leaders — this role is designed for a driven, analytically-minded professional who thrives at the intersection of strategy, finance, and organizational execution. The Chief of Staff will accelerate key initiatives, ensure leadership alignment, and bring operational rigor to the highest-priority work across the company.
Executive Leadership Support
- Act as a trusted partner and right hand to the CEO and CFO, helping drive their most important strategic priorities forward
- Own and manage the CEO's calendar — prioritizing meetings, protecting focus time, and ensuring agenda alignment with company objectives
- Attend key executive meetings, capture decisions and action items, and drive accountability across the organization for follow-through
- Prepare executive briefings, board materials, and presentations that communicate complex topics with clarity and precision
- Represent the CEO and CFO in internal and external meetings as needed, providing continuity and follow-up
Strategy & Planning
- Support the development and execution of the company's strategic plan, OKRs, and annual operating priorities
- Coordinate and manage the cadence of Quarterly and Monthly Business Reviews — including agenda development, cross-functional data collection, and post-meeting follow-up
- Identify organizational bottlenecks or misalignments, and work proactively to resolve them
- Facilitate cross-functional working sessions and ensure key decisions are made efficiently and on time
Finance & FP&A Support
- Support FP&A activities including financial modeling, scenario analysis, and business case development for strategic initiatives
- Assist in the preparation and review of budget materials, variance analyses, and executive financial reporting
- Partner with the Finance team on forecasting, headcount planning, and other operational finance workflows
- Help synthesize financial data and metrics into clear narratives for leadership and board consumption
Organizational Operations
- Drive follow-up and accountability across the organization on CEO and CFO priorities — tracking progress and escalating risks proactively
- Design and manage internal communication rhythms, ensuring consistent information flow across teams
- Lead or support special projects and cross-functional initiatives as directed by the CEO or CFO
What We're Looking For:
Education & Experience
- Bachelor's degree required; MBA or equivalent graduate degree strongly preferred
- 5 years of experience in management consulting, investment banking, FP&A, corporate strategy, or a similar analytically rigorous role
- Experience in the SaaS industry
Skills & Competencies
- Exceptional financial modeling and analytical skills — fluency in Excel, PowerPoint, AI and business intelligence tools
- Outstanding written and verbal communication; able to distill complex information into clear, executive-ready narratives
- Strong project management skills with the ability to manage multiple high-priority workstreams simultaneously
- High emotional intelligence — discreet, trustworthy, and skilled at navigating organizational dynamics with diplomacy
- Proactive self-starter with a bias toward action; comfortable with ambiguity and able to operate without a detailed playbook
- Detail-oriented and highly organized
Top Skills
AI
Business Intelligence Tools
Excel
PowerPoint
Similar Jobs
Healthtech
The Chief of Staff will advise the executive team, manage strategic projects, ensure organizational alignment, and facilitate communication across teams.
Top Skills:
Microsoft Office Suite
Cloud • Security • Software
The Chief of Staff to the CRO operates as a strategic partner to advance the global revenue organization by aligning leaders, managing operational processes, and supporting key revenue initiatives.
Information Technology • Consulting
The Chief of Staff will support the CMO, drive strategic marketing initiatives, manage cross-team connectivity, and enhance stakeholder communication.
What you need to know about the Boston Tech Scene
Boston is a powerhouse for technology innovation thanks to world-class research universities like MIT and Harvard and a robust pipeline of venture capital investment. Host to the first telephone call and one of the first general-purpose computers ever put into use, Boston is now a hub for biotechnology, robotics and artificial intelligence — though it’s also home to several B2B software giants. So it’s no surprise that the city consistently ranks among the greatest startup ecosystems in the world.
Key Facts About Boston Tech
- Number of Tech Workers: 269,000; 9.4% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: Thermo Fisher Scientific, Toast, Klaviyo, HubSpot, DraftKings
- Key Industries: Artificial intelligence, biotechnology, robotics, software, aerospace
- Funding Landscape: $15.7 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Summit Partners, Volition Capital, Bain Capital Ventures, MassVentures, Highland Capital Partners
- Research Centers and Universities: MIT, Harvard University, Boston College, Tufts University, Boston University, Northeastern University, Smithsonian Astrophysical Observatory, National Bureau of Economic Research, Broad Institute, Lowell Center for Space Science & Technology, National Emerging Infectious Diseases Laboratories
