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Diligent · 2 days ago

Director, Commercial Finance & Operations

Washington, DC

Full-time

Hybrid

Director/Executive

$151K/yr - $194K/yr

10+ years exp

Diligent is an AI leader in governance, risk and compliance SaaS solutions, seeking a highly analytical and business-oriented Director of Commercial Finance & Operations. This role will serve as a core financial partner, driving planning, forecasting, investment evaluation, and operational insights to improve Gross Dollar Retention and overall post-sales efficiency.

Business IntelligenceCollaborationComplianceData CenterInformation TechnologyMeeting SoftwareMessagingRisk ManagementSaaSSoftware

Responsibilities

Support Post-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

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

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

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

Qualification

Financial modelingSaaS experienceAnalytical skillsERP financial systemsGTM metricsProcess improvementCommunication skillsInterpersonal skillsCollaboration

Required

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