insightsoftware · 2 days ago
Chief of Staff
United States
Full-time
Remote
Director/Executive
7+ years expinsightsoftware is a global provider of reporting, analytics, and performance management solutions that empower leaders to make intelligent decisions. They are seeking a Chief of Staff to serve as a strategic partner to the President & General Manager, driving operational excellence and orchestrating a transformation into a unified AI-first platform.
AccountingAnalyticsBusiness IntelligenceConsultingFinancial ServicesSoftware
Responsibilities
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
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
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
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
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
Qualification
Required
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
Preferred
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
Company
insightsoftware
insightsoftware is the most comprehensive provider of solutions for the Office of the CFO.
1001-5000 employees
Funding
Current Stage
Late StageTotal Funding
$1BKey Investors
Hg
2021-07-13Private Equity· $1B
2019-08-15Private Equity
2018-06-14Acquired
Leadership Team
Bernie Emsley
Chief Technology Officer
Meg Christman
Executive Vice President Delivery Services
Recent News
Business Wire
2025-12-09
Company data provided by crunchbase