Director, Commercial Finance & Operations

About Us

Diligent is the AI leader in governance, risk and compliance (GRC) SaaS solutions, helping more than 1 million users and 700,000 board members to clarify risk and elevate governance. The Diligent One Platform gives practitioners, the C-Suite and the board a consolidated view of their entire GRC practice so they can more effectively manage risk, build greater resilience and make better decisions, faster.

At Diligent, we're building the future with people who think boldly and move fast. Whether you're designing systems that leverage large language models or part of a team reimaging workflows with AI, you'll help us unlock entirely new ways of working and thinking. Curiosity is in our DNA, we look for individuals willing to ask the big questions and experiment fearlessly - those who embrace change not as a challenge, but as an opportunity.

The future belongs to those who keep learning, and we are building it together. At Diligent, you're not just building the future - you're an agent of positive change, joining a global community on a mission to make an impact.

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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

* 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.

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,…