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.

The Director of Product Management, Lease Lifecycle Management, is a strategic leader and executive owner of our enterprise lease management and administration solutions within our comprehensive suite of financial software platforms. This senior leadership role is responsible for driving market dominance, commercial growth, and transformative customer impact within our Lease Lifecycle Management portfolio, with an executive focus on business value creation, strategic go-to-market execution, and enterprise-wide customer engagement. 

As the senior market authority and customer advocate for the Lease Lifecycle Management product segment, you will own the end-to-end product strategy and execution, from technical feasibility assessment and enterprise architectural alignment to commercial leadership and customer adoption at scale. Leading cross-functional teams including Engineering, UX, Product Marketing, and Sales, you will ensure our lease management solutions are technically superior, highly scalable, and aligned with evolving global lease accounting standards and compliance requirements. 

Our Lease Lifecycle Management solutions, including LeaseAccelerator, EZLease, PureLease, and Real Estate Manager, empower multi-national enterprise teams to gain real-time insights and make faster, data-driven decisions about their lease portfolios, lease accounting compliance (ASC 842/IFRS 16), lease administration automation, and strategic portfolio optimization, driving continuous business improvement and ensuring adherence to complex regulatory requirements while optimizing operational efficiency. 

Key Responsibilities 

1. Strategic Product Leadership & Vision 

• Define and drive the enterprise-wide technical product strategy for Lease Lifecycle Management solutions, ensuring alignment with global lease accounting standards (ASC 842, IFRS 16), compliance requirements, and modern cloud-first enterprise technology strategies 

• Lead the development of high-performance, scalable lease management platforms that seamlessly integrate with major ERP and EPM systems including Oracle, SAP, Microsoft Dynamics, NetSuite, Workday. 

• Validate, architect, and execute the long-term product roadmap and portfolio strategy for both immediate market needs and 3-5 year growth by collaborating with internal and external stakeholders, including Fortune 500 customers, lease advisory partners, regulatory bodies, Marketing, Sales, and Customer Success 

• Leverage strategic partnerships with lease technology providers, real estate consulting firms, and regulatory organizations to accelerate innovation and create sustainable competitive advantages 

• Form strategic cross-portfolio partnerships with other insightsoftware business units to drive unified platform opportunities and customer expansion 

• Extract maximum commercial value from your product portfolio through sophisticated packaging, pricing optimization, strategic feature development, and market enablement 

• Champion AI-powered lease abstraction capabilities and agentic automation to revolutionize lease data extraction and administration workflows 

2. Business Leadership & Go-to-Market Excellence 

• Own and optimize the complete business performance of the Lease Lifecycle Management portfolio, delivering strategic recommendations to accelerate commercial growth and exceed financial targets 

• Drive portfolio expansion through strategic market penetration, lessor functionality expansion, and international market development 

• Transform complex technical innovations into compelling customer-centric solutions, ensuring enterprise lease professionals can derive actionable insights from consolidated lease portfolio data across global operations 

• Partner strategically with Sales, Marketing, and Customer Success leadership to ensure premium positioning, competitive pricing, and sophisticated value articulation of Lease Management products to C-suite executives 

• Execute comprehensive product launch strategies, partnering with Product Marketing and Sales Enablement to deliver executive-level product education, demonstrations, and thought leadership to internal teams and enterprise customers 

• Drive and lead enterprise-wide sales and customer education programs to ensure comprehensive understanding of product capabilities, competitive differentiation, and consultative selling methodologies 

• Develop and execute strategic pricing frameworks, including enterprise price optimization, competitive market analysis, and value/consumption-based pricing models. 

• Lead cross-sell initiatives across the insightsoftware portfolio to drive bi-directional revenue growth 

3. Product Development & Technical Execution 

• Drive delivery of complex market and enterprise customer requirements, including strategic definition, prioritization, technical trade-offs, and execution of major release milestones 

• Address critical competitive gaps in integration capabilities, lessor functionality, and international accounting standards support identified through loss analysis 

• Lead platform consolidation initiatives to unify disparate lease solutions and create seamless user experiences across the portfolio 

• Drive exceptional customer experiences across the entire lease lifecycle (procurement, administration, accounting, compliance, reporting), measured by NPS, retention, and customer expansion metrics 

• Lead resolution of enterprise customer escalations, retention challenges, and strategic account management issues 

• Oversee migration strategies for customers to flagship platforms 

4. Market Leadership & Customer Strategy 

• Develop comprehensive market intelligence on customer usage patterns, competitive positioning, and global lease management trends, translating insights into strategic product requirements and market opportunities 

• Serve as the recognized thought leader for enterprise lease management software, leading industry conferences, webinars, FASB/IASB panels, advisory boards, and customer executive briefings 

• Execute sophisticated win/loss analysis and customer feedback programs (including executive NPS interviews and strategic customer advisory boards) to refine product capabilities and enhance enterprise user experiences 

• Monitor global lease accounting regulatory changes, compliance requirements, and competitive landscape evolution, ensuring our solutions maintain market leadership and regulatory compliance across all jurisdictions 

• Function as the primary internal product evangelist and sought-after external market authority for enterprise lease lifecycle management solutions 

• Identify strategic market opportunities through comprehensive market analysis, executive customer interviews, and competitive intelligence programs 

• Lead competitive positioning against competitors while capturing disruption opportunities 

Technical & Domain Expertise 

• Deep expertise in enterprise lease management software, lease accounting processes, and global lease compliance requirements 

• Extensive experience with lease accounting platforms, lease administration systems, and enterprise real estate management technologies 

• Strong understanding of global lease accounting standards (ASC 842, IFRS 16, GASB 87/96), lease administration best practices, and multinational compliance requirements 

• Understanding of modern data analytics, business intelligence platforms, and real-time reporting technologies in the context of lease portfolio management 

• Growing understanding and enthusiasm for artificial intelligence and the potential it has to revolutionize lease abstraction, administration automation, and portfolio optimization 

• Experience with enterprise software architectures, cloud platforms, and their impact on financial software solutions at scale 

• Knowledge of advanced software development methodologies (Agile, DevOps, CI/CD) and enterprise-grade security frameworks desirable 

Product & Business Leadership 

• 10+ years of experience in B2B enterprise software Product Management, with at least 5 years in senior leadership roles focused on lease management, real estate, or financial compliance solutions 

• Proven ability to bridge complex technical and business requirements, ensuring lease management solutions drive measurable enterprise business value and ROI 

• Extensive experience in SaaS/cloud-based product leadership, with deep expertise in financial data analytics, reporting, and enterprise integrations 

• Strong P&L ownership mindset, making strategic product investment decisions based on market opportunity, technical feasibility, and competitive positioning 

• Demonstrated success engaging with C-suite executives, CFOs, Controllers, Real Estate Directors, and enterprise IT leadership to drive adoption and strategic business outcomes 

• Expertise in enterprise pricing strategy development and implementation, including value-based pricing and competitive positioning 

• Proven track record managing complex product metrics including bookings, ARR, net expansion, gross retention, and customer lifetime value 

• Experience driving product rationalization and portfolio optimization strategies 

Executive Leadership & Communication 

• Proven ability to influence and lead cross-functional organizations without formal authority, driving alignment across Engineering, Sales, Marketing, and Customer Success 

• 5+ years of experience building, managing, and developing high-performing product management and technical teams 

• Exceptional executive communication and presentation skills, with demonstrated ability to present to boards of directors, C-suite executives, and industry analyst organizations 

• Ability to balance competing enterprise priorities and make critical strategic decisions under pressure 

• Extensive experience partnering with Product Marketing leadership to commercialize complex enterprise offerings 

• Experience leading UX and design organizations to create intuitive, accessible enterprise solutions 

• Demonstrated ability to drive execution across global Development, Sales, Marketing, Support, and Customer Success organizations 

Education & Certifications 

• Bachelor's degree (or foreign equivalent) in Business, Computer Science, Engineering, Finance, Accounting, Real Estate, or related field 

• Professional qualification or Master's degree in Business (MBA), Finance, Real Estate, or related field strongly preferred 

• Beneficial Certifications: CPA, CMA, CCIM (Certified Commercial Investment Member), CPM (Certified Property Manager), Pragmatic Marketing, CSPO, or Enterprise Lease Technology certifications 

• Professional or in-house experience and certification in lease accounting standards (ASC 842, IFRS 16), real estate management, or equipment finance preferred 

Additional Requirements 

• Executive presence with exceptional organizational and strategic planning capabilities 

• Strategic visionary with disciplined tactical execution - ability to balance long-term market vision with rigorous operational excellence 

• Executive drive and resilience - ability to operate in demanding enterprise environments with unwavering focus on achieving exceptional results 

• Compelling executive presence - ability to effectively engage with enterprise prospects, Fortune 500 customers, and industry leaders, building confidence in our strategic direction 

• Market authority - recognized expertise in lease lifecycle management, with ability to speak authoritatively on industry trends, regulatory changes, and best practices 

• Comfortable with 25-35% executive travel for customer meetings, industry events, and team leadership 

#LI-Remote

** 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.