Vice President, AI Transformation & Services

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 seeking a Vice President of AI Transformation & Services to lead our customer-facing services organization and drive measurable customer outcomes across our SaaS platform. This leader will own the delivery of strategic, optimization, and advisory services for our core product while building and scaling an AI Enablement & Consulting practice that helps customers maximize value from emerging AI capabilities.

The VP of Professional Services will be responsible for improving customer retention, adoption, and long-term value realization while operating Professional Services as a self-sustaining business unit with strong utilization, project delivery, and financial performance.

This position is 100% remote position open to candidates in the Eastern time zone in the United States. No sponsorship or relocation assistance is available.

What You’ll Do

• Lead all Professional Services engagements, including product optimization, strategic advisory, workflow transformation, and value realization initiatives.
• Build and scale an AI Enablement & Consulting practice, including service offerings, methodologies, and customer-facing solutions.
• Drive customer outcomes that increase product adoption, retention, expansion, and overall customer lifetime value.
• Own Professional Services financial performance, ensuring the organization operates as a self-funding business unit with clear revenue, margin, and utilization targets.
• Establish and monitor KPIs for project delivery, resource utilization, customer satisfaction, retention impact, and profitability.
• Develop project management standards, customer communication frameworks, and governance processes to ensure successful delivery and measurable business outcomes.
• Partner closely with Customer Success, Sales, Product, and Engineering teams to align services offerings with customer needs and company strategy.
• Identify, package, and commercialize new consulting and AI-focused service offerings that create customer value and drive revenue growth.
• Recruit, develop, and lead a high-performing team of consultants, project managers, and subject matter experts.

Requirements

• 10+ years of experience leading Professional Services, Consulting, Customer Success, or related functions within a SaaS environment.
• Proven track record of building and scaling customer-facing consulting or professional services organizations.
• Experience managing services P&L, utilization, project delivery, and revenue generation.
• Strong understanding of customer adoption, retention, and value realization strategies.
• Experience developing AI-related consulting, transformation, or enablement services is highly preferred.
• Exceptional leadership, communication, and executive stakeholder management skills.

Successs Measures

• Improved customer retention and product adoption.
• Increased customer value realization and expansion opportunities.
• High project delivery quality, consultant utilization, and customer satisfaction.
• Growth and profitability of AI Enablement & Consulting services.
• Professional Services operating as a profitable, self-sustaining business unit.

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 

Equal Opportunity

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.