Chief of Staff

About Us

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insightsoftware is a global provider of reporting, analytics, and performance management solutions that unlock the potential of business data and transform the way finance and data teams operate. We empower leaders from over 32,000 organizations to make timely and intelligent decisions. Our comprehensive solutions span Financial Planning and Analysis (FP&A), Controllership, and Data and Analytics. We deliver finance teams the insights required to navigate any economic climate and drive greater financial intelligence, while increasing productivity, visibility, accuracy, and compliance. Learn more at insightsoftware.com.

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Job Description

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Position Overview

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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.

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Key Responsibilities

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Strategic Leadership & Executive Partnership

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• 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 

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Business Unit Operations Excellence

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• 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 

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Portfolio Rationalization & Platform Consolidation

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• 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 

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Organizational Development

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• 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

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Communication & Stakeholder Management

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• 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 initiatives and corporate planning cycles 
• Facilitate alignment between dedicated Data + Analytics resources and shared corporate services 

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What Success Looks Like

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SDP execution excellence: Quarterly cycles complete on time with clear X-Matrix accountability and <5% variance to committed deliverables 

• Platform consolidation milestones achieved with measurable customer migration progress and technical debt reduction 
• Operational rhythm established: Weekly/monthly reporting cadence with executive dashboards providing real-time visibility into business performance 
• Internal AI adoption: Documented productivity improvements from AI-first capabilities embedded in daily operations 
• 90%+ customer retention 
• Cross-functional alignment and "good corporate citizen" reputation 

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Qualifications

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Required Qualifications:

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• 7-10+ years progressive experience in product operations, operational strategy, chief of staff, or management consulting roles, preferably in B2B SaaS or enterprise software 
• Proven experience with product portfolio rationalization, particularly in on-premise or hybrid deployment models where customer control and technical complexity drive migration strategy 
• Strong operational execution: experience building dashboards, metrics frameworks, and operational cadences that drive accountability and business performance 
• Demonstrated success driving technology adoption and change management across business units, particularly with AI/ML capabilities 
• Proven track record leading complex, cross-functional initiatives and organizational transformations 
• Strong strategic thinking with exceptional analytical and problem-solving capabilities 
• Outstanding communication and presentation skills; ability to influence without authority 
• Comfort operating in ambiguous, fast-paced environments with competing priorities 
• Bachelor's degree required; MBA or advanced degree strongly preferred 

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Preferred Qualifications

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• Product operations background in data/analytics, embedded software, or enterprise infrastructure companies 
• Experience managing on-premise software portfolios through cloud transformation or platform consolidation initiatives 
• Background in regulated industries (financial services, healthcare, manufacturing) with understanding of customer-controlled deployment models 
• Working knowledge of Hoshin Kanri, X-Matrix, or similar strategic deployment methodologies (OKRs, V2MOM) 
• Experience with BI/analytics tools (Tableau, PowerBI, Looker) and building executive reporting frameworks 
• Previous Chief of Staff or similar strategic leadership role experience 

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Why This Matters

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This is a once-in-a-career transformation opportunity: consolidate 14 products into a unified AI-first platform serving 3,600+ enterprise customers who embed our intelligence into their mission-critical products. You'll be the operational architect of this 3-year journey, working directly with a President & GM who's led multiple successful exits across startups and $1B+ unicorns.

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The market opportunity is compelling: we're defining a new category—Intelligent Infrastructure—in a $4B+ market where cloud-native competitors can't compete. Your operational excellence will shape how we capture this white space.

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Our North Star: Make our customers' products the smartest person in the room.

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Additional Information

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All your information will be kept confidential according to EEO guidelines.

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Learn more about our high-energy, high-performance global team: Work With Us

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insightsoftware About Us: Hear From Our Team

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Background checks are required for employment with insightsoftware, where permitted by country, state/province.

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At insightsoftware, we are committed to equal employment opportunity regardless of race, color, ethnicity, ancestry, religion, national origin, gender, sex, gender identity or expression, sexual orientation, age, citizenship, marital or parental status, disability, veteran status, or other class protected by applicable law. We are proud to be an equal opportunity workplace.