Chief of Staff

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.

Position Overview 

Seeking an exceptional Chief of Staff to serve as strategic partner to the President & General Manager, driving operational excellence across our $122M ARR Data + Analytics business. This role orchestrates our transformation from 14 fragmented 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 across Connect, Analyze, Collaborate, and Intelligence product categories 

• 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 and optimize the day-to-day operating cadence for the Data + Analytics business through standups, monthly executive reviews, and strategic review sessions 

• Drive internal adoption and evangelism of AI-first transformation across the business, embedding AI capabilities and mindset into all operations and decision-making 

• Establish and drive comprehensive metrics review framework covering pipeline, bookings, ARR, retention, and product performance across product pillars 

• Lead cross-functional goal setting that aligns with company Rally Cry and strategic objectives 

Portfolio Rationalization & Platform Consolidation 

• Spearhead product rationalization initiative to consolidate 14 products into unified platform under Simba brand 

• Execute 3-year portfolio migration strategy moving $45M+ ARR from legacy products to modern platforms. 

• Lead business transformation initiatives including brand consolidation, unified go-to-market positioning, and platform integration roadmap 

• Drive business transformation initiatives including organizational design, process optimization, 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 (marketing, web, automation) while maintaining business 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 initiatives and corporate planning cycles 

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

What Success Looks Like: 

• SDP execution with clear X-Matrix accountability and quarterly goal achievement 

• Platform consolidation milestones achieved: 14→5 products by FY28 

• 90%+ customer retention through no-force migration strategy 

• AI adoption metrics showing internal transformation progress 

• Operational excellence enabling $122M→$130M ARR growth trajectory 

• Cross-functional alignment and "good corporate citizen" reputation 

Required Qualifications: 

• 7-10+ years progressive experience in strategy, operations, or management consulting roles, preferably in B2B SaaS or enterprise software 

• 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 

• Experience with portfolio rationalization, product consolidation, or platform transformation initiatives 

• Comfort operating in ambiguous, fast-paced environments with competing priorities 

• Bachelor's degree required; MBA or advanced degree strongly preferred 

Preferred Qualifications: 

• Experience in data/analytics, embedded software, or AI/ML product companies 

• Background in regulated industries (financial services, healthcare, manufacturing) 

• Familiarity with Hoshin Kanri, X-Matrix, or similar strategic deployment methodologies 

• Understanding of on-premise software business models and hybrid cloud transitions 

• Previous Chief of Staff or similar strategic leadership role experience 

Why This Matters 

• You'll help steer how 3,600+ customers—including Microsoft, Databricks, Snowflake, HSBC, Qlik—think about embedding trusted intelligence into enterprise products. This is the rare combination of meaningful scale ($122M ARR business targeting $150M+ over 3 years) with genuine transformation opportunity. Prove that AI-augmented marketing delivers exponential leverage while establishing new category leadership in a $4B+ regulated enterprise market. 
   

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

** At this time insightsoftware is not able to offer sponsorship to candidates who are not eligible to work in the country where the position is located. **

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

insightsoftware About Us: Hear From Our Team - InsightSoftware (wistia.com)

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

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.