Director, Commercial Financial

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, results-oriented, collaborative environment. 

U.S pay range

$131,000 - $180,000 CAD

What Diligent Offers You 

• Creativity is ingrained in our culture. We are innovative collaborators by nature. We thrive in exploring how things can be differently both in our internal processes and to help our clients
• We care about our people. Diligent offers a flexible work environment, global days of service, comprehensive health benefits, meeting free days, generous time off policy and wellness programs to name a few
• We have teams all over the world. We may be headquartered in New York City, but we have office hubs in Washington D.C., Vancouver, London, Galway, Budapest, Munich, Bengaluru, Singapore, and Sydney.
• Diversity is important to us. Growing, maintaining and promoting a diverse team is a top priority for us. We foster and encourage diversity through our Employee Resource Groups and provide access to resources and education to support the education of our team, facilitate dialogue, and foster understanding.

Diligent created the modern governance movement. Our world-changing idea is to empower leaders with the technology, insights and connections they need to drive greater impact and accountability – to lead with purpose. Our employees are passionate, smart, and creative people who not only want to help build the software company of the future, but who want to make the world a more sustainable, equitable and better place. 

Headquartered in New York, Diligent has offices in Washington D.C.,  London, Galway, Budapest, Vancouver, Bengaluru, Munich, Singapore and Sydney.   To foster strong collaboration and connection, this role will follow a hybrid work model. If you are within a commuting distance to one of our Diligent office locations, you will be expected to work onsite at least 50% of the time. We believe that in-person engagement helps drive innovation, teamwork, and a strong sense of community.

We are a drug free workplace. Diligent is proud to be an equal opportunity employer. We do not discriminate based on race, color, religious creed, sex, national origin, ancestry, citizenship status, pregnancy, childbirth, physical disability, mental disability, age, military status, protected veteran status, marital status, registered domestic partner or civil union status, gender (including sex stereotyping and gender identity or expression), medical condition (including, but not limited to, cancer related or HIV/AIDS related), genetic information, or sexual orientation in accordance with applicable federal, state and local laws. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. See also Diligent's EEO Policy and Know Your Rights. We are committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. If you need assistance or an accommodation due to a disability, you may contact us at

To all recruitment agencies: Diligent does not accept unsolicited agency resumes. Please do not forward resumes to our jobs alias, Diligent employees or any other organization location. Diligent is not responsible for any fees related to unsolicited resumes.

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