Chief of Staff

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