Chief of Staff

Company Description

insightsoftware is a global provider of comprehensive solutions for the Office of the CFO. We believe an actionable business strategy begins and ends with accessible financial data. With solutions across financial planning and analysis (FP&A), accounting, and operations, we transform how teams operate, empowering leaders to make timely and informed decisions. With data at the heart of everything we do, insightsoftware enables automated processes, delivers trusted insights, boosts predictability, and increases productivity. Learn more at insightsoftware.com.

Job Description

Position Overview 

Seeking an exceptional Chief of Staff to serve as strategic partner to the President & General Manager, driving operational excellence across our $100M+ ARR Data + Analytics business. This role orchestrates our transformation from 14 point products into a unified AI-first platform, executing our mission to make intelligent products the standard. 

Key Responsibilities 

Strategic Leadership & Executive Partnership 

• Partner with President & General Manager on strategic planning, decision-making, and priority setting the entire product portfolio 

• Drive business unit-wide strategic initiatives through the Strategic Deployment Process (SDP), ensuring alignment between corporate objectives and business unit execution 

• Lead quarterly SDP cycles, X-Matrix development, and accountability frameworks 

• Represent the President & General Manager in senior leadership meetings and cross-functional forums when needed 

Business Unit Operations Excellence 

• Own the daily operating cadence for the Data + Analytics business through weekly leadership reviews, monthly executive reviews, and strategic review sessions 

• Design and maintain executive dashboards tracking pipeline, bookings, ARR, retention, product performance, and platform migration progress across product pillars 

• Drive SDP process adherence and execution discipline, ensuring quarterly cycles complete on time with clear X-Matrix accountability and measurable outcomes 

• Lead cross-functional goal setting that aligns with company Annual Operating Plan and strategic SDP objectives, translating strategy into measurable quarterly commitments 

• Establish comprehensive metrics review framework and deliver weekly/monthly operational reports to leadership team and board 

• Champion internal AI adoption, identifying use cases for natural language interfaces, proactive intelligence, and workflow automation that improve operational productivity 

Portfolio Rationalization & Platform Consolidation 

• Spearhead product rationalization to consolidate 14 point products into unified platform, leveraging product operations expertise to manage dependencies, technical debt, and migration sequencing 

• Support product portfolio roadmap alignment with platform consolidation strategy, working closely with VP of Product Management and engineering leaders 

• Partner on technical complexity of on-premise deployments, customer-controlled environments, and hybrid cloud transitions during platform consolidation 

• Drive execution of 3-year portfolio migration strategy from legacy products to modern platforms, balancing customer retention with platform velocity 

• Own product lifecycle management across legacy and modern platforms, establishing sunset timelines and migration incentives 

• Coordinate business transformation initiatives including brand consolidation, unified go-to-market positioning, organizational design, and operational improvements 

• Oversee strategic projects such as market expansion, partner ecosystem development, and customer migration programs 

Organizational Development 

• Lead organizational structure optimization and design, working with HR on hiring strategy and talent development 

• Support executive team through talent assessment, succession planning, and team development initiatives 

• Foster effective collaboration with centralized teams (HR, Finance, Legal, IT) while maintaining business unit autonomy as a 'good corporate citizen’ 

Communication & Stakeholder Management 

• Facilitate internal communications, ensuring consistent messaging around AI-first positioning and unified platform vision 

• Prepare executive-level materials, presentations, and board updates 

• Coordinate business participation in company-wide initiative