Vice President, Professional Services

Datarails

1d•$250,000 - $300,000•Remote

About The Position

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 Professional 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.

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.
Exceptional leadership, communication, and executive stakeholder management skills.

Nice To Haves

Experience developing AI-related consulting, transformation, or enablement services is highly preferred.

Responsibilities

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.

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
Meaningful equity
401(k) plan with up to 4% match
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