[Hiring] Vice President of Customer Success @Datarails

Role Description

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 Own

• 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

Qualifications

• 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

Benefits

• 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