Vice President, Customer Success

Description Datarails is transforming how finance teams operate by bringing together data, automation, and AI into a unified platform for modern FP&A. We empower finance leaders to move faster, reduce risk, and make better decisions - without leaving the tools they already trust. As we enter our next phase of growth, we are evolving Customer Success into a strategic function that not only supports retention and expansion, but also shapes how customers adopt AI and data-driven workflows across the finance organization. We are looking for a Vice President of Customer Success to lead and elevate our global Customer Success organization. This leader will drive customer outcomes, retention, and expansion while helping define how finance teams adopt AI-enabled workflows within FP&A. This role requires a strategic operator who understands technology and data at a business level - without needing to be deeply technical - and who is excited to help customers navigate the shift toward AI-powered finance. You will partner closely with the Chief Customer Officer and cross-functional leaders across Product, Sales, Marketing and Operations to ensure customers are realizing measurable value and that Customer Success is a true growth engine for the business. What You’ll Do Customer Strategy & Outcomes Define and execute a global Customer Success strategy aligned to retention, expansion, and long-term customer value Build customer journey frameworks that drive adoption, engagement, and measurable business impact Elevate Customer Success from reactive support to proactive, insight-driven partnership AI & Modern FP&A Adoption Help shape how customers adopt AI-enabled workflows within finance and FP&A processes Partner with Product to translate AI capabilities into real customer value and use cases Guide Customer Success teams in positioning AI as a practical enabler—not a theoretical concept Team Leadership & Scale Lead, develop, and scale a high-performing global Customer Success organization Build a culture of accountability, curiosity, and continuous improvement Establish clear success metrics, operating rhythms, and performance visibility Revenue & Growth Alignment Partner closely with Sales and Revenue leadership to drive expansion, renewals, and customer health Identify and operationalize opportunities for upsell, cross-sell, and increased product adoption Ensure Customer Success is tightly aligned to revenue goals and business outcomes Customer Insight & Product Influence Act as the voice of the customer internally, influencing product direction and roadmap Build strong feedback loops between Customer Success, Product, and Engineering Leverage customer data and insights to inform strategic decisions Requirements 6+ years of experience in Customer Success, Account Management, or related functions, with at least 2+ years in senior leadership roles Proven success leading Customer Success in a SaaS, fintech, or data-driven environment Strong understanding of customer lifecycle management, retention strategy, and expansion models Comfortable working with data, analytics, and technology concepts without needing to be deeply technical Demonstrated ability to lead through change and scale teams in high-growth environments Experience partnering cross-functionally with Product, Sales, and executive leadership Strong executive presence with the ability to influence both internally and externally Preferred Experience Experience in FP&A, finance tools, or working closely with finance stakeholders (CFOs, FP&A leaders) Familiarity with AI-enabled products or experience driving adoption of new technology paradigms Background in venture-backed or high-growth SaaS environments What We Offer A collaborative, team-oriented environment, the ability to own your schedule (work your local time zone), and the opportunity to grow at Datarails over many years The target OTE salary range will be between 250-300 OTE USD per year, based on multiple factors including prior experience, skills, and location. We are open to candidates with varying levels of experience. Meaningful equity 401(k) plan with up to 4% match and HSA & FSA Options 100% paid medical, dental, and vision coverage for employees and 100% paid medical and 80% paid dental and vision coverage for dependents $540/year toward glasses, sunglasses, or contact lenses from XP Health for employees enrolled in any Guardian Vision plan Calm app membership Paternity leave Flexible, unlimited sick time and PTO (we recommend 18-25 vacation days annually) 12 paid company holidays Life insurance CPA/CFA license renewal reimbursement We want to make sure everyone has an equal chance to participate and make a difference. Datarails is an equal opportunity employer and prioritizes building a diverse and inclusive workplace. We provide equal employment opportunities to all employees and applicants of any type and do not discriminate based on race, color, religion, national origin, gender, age, sexual orientation, physical or mental disability, genetic information or characteristic, gender identity and expression, veteran status, or other non-job related characteristics or other prohibited grounds specified in applicable federal, state, and local laws. Datarails’ policy is to comply with all applicable laws related to nondiscrimination and equal opportunity and will not tolerate discrimination or harassment based on any of these characteristics. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.

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