Position Overview
Diligent is seeking a highly analytical and business-oriented Director of Commercial Finance & Operations to partner with the global Post-Sales organization (Customer Success, Support, Professional Services, and Onboarding). This role will serve as a core financial partner, driving planning, forecasting, investment evaluation, and operational insights that improve Gross Dollar Retention (GDR) and overall post-sales efficiency.
You will collaborate closely with Post-Sales leaders, FP&A, and cross-functional partners to translate strategy into measurable financial and operational outcomes. This is a high-visibility, high-impact role reporting to the Senior Director of Post-Sales Finance & Operations.
Key Responsibilities:
Strategic & Operational Leadership
- SupportPost-Sales leadership to translate strategy into an executable operating model, including capacity planning, segmentation, coverage design, service model evolution, process improvement, and KPI frameworks aligned to long-term financial and GDR objectives.
- Provide analytical support to the Post-Sales leadership team on long-range operating model design (role mix, digital/self-serve motions, AI-enabled service models).
- Evolve the Post-Sales KPI framework (leading indicators, performance guardrails, operational diagnostics) and use it to drive disciplined, data-backed decision-making.
- Standardize processes for investment intake, business cases, and ROI analysis across CS, PS, Support, and Onboarding.
- Support the Post-Sales GDR improvement roadmap through financial modeling, risk/opportunity identification, and investment evaluation.
Planning, Forecasting & Analytics
- Manage the monthly, quarterly, and annual planning processes, setting credible, data-driven targets and integrating them into the company’s financial model for executive and board review.
- Deploy AI-enabled forecasting frameworks, including automated variance explanations, scenario modeling, and early-warning risk detection.
- Evaluate the financial impact of proposed retention initiatives and investments; build models to assess scenario-based impact on GDR.
- Create and deliver clear, executive-ready financial and operational analyses for the Post-sales leadership team, CFO, and broader leadership teams.
Systems, Data & AI Enablement
- Partner with GTM Systems and Data teams to leverage tools such as Gainsight, Snowflake, Fullcast, and Adaptive to drive automated insights, churn analytics, and scalable capacity planning..
- Direct the headcount and resource allocation strategy and planning for Post-Sales, ensuring optimal deployment to maximize ROI and achieve long-range goals.
Stakeholder Leadership & Execution
- Deliver timely and accurate executive-level reporting and insights, elevating transparency and accountability across Post-Sales.
- Build and maintain strong, collaborative relationships across FP&A, Accounting, Sales Ops, HR, Legal, and the broader Diligent leadership community.
Required Experience:
- 10+ years of experience working in a senior financial and strategy & operations role in a complex organization, preferably a SaaS / computer software company.
- Excellent analytical, financial modeling/ MS Excel, and communication skills; in-depth experience with financial analysis and a strong understanding of GTM metrics.
- Strong financial modeling experience and a willingness to dig into the details.
- Advanced skill level in ERP financial systems.
- Experience creating annual plans for a GTM organization from the ground up.
- Proven ability to establish strategic, high-impact initiatives, defining performance indicators and operational focus.
- Ability to influence through outstanding interpersonal skills and build collaborative relationships and consensus among, multiple stakeholders with varying points of view.
- Ability to thrive in a fast-paced, results-oriented, collaborative environment.
