Head of Digital & AI Transformation

Summary

Join SingleStore as the Head of Digital & AI Transformation, a pivotal leadership role accelerating the company's digital and AI maturity. Reporting to the VP of Analytics, you will spearhead the enterprise's IT strategy, encompassing business application management and the AI & Automation Center of Excellence (CoE). Drive digital transformation, process optimization, and adoption of advanced AI and automation solutions. Lead and inspire a high-performing team to deliver measurable improvements in efficiency and financial performance. Shape company culture and operational excellence in a fast-growing tech environment. This position requires a bold vision for technology and proven change leadership.

Requirements

• Bachelor’s degree in Computer Science, Information Technology, Business, Engineering, or a related field (Master’s or MBA preferred)
• Minimum 10 years of experience in IT management, digital transformation, or related fields, with significant leadership exposure and cross-functional team leadership
• Direct experience delivering enterprise-scale digital transformation projects, preferably in SaaS, cloud, or data infrastructure contexts
• Deep expertise with AI, machine learning, automation technologies, and systems integration
• Strong background in strategic planning, change management, and project management methodologies (e.g., Agile, Lean, Six Sigma)
• Demonstrated ability to manage IT budgets, oversee resource allocation, and drive financial efficiency
• Outstanding communication, interpersonal, and collaboration skills—capable of influencing at all organizational levels
• Track record of integrating emerging digital solutions and navigating dynamic, high-growth business environments

Responsibilities

• Develop and execute a comprehensive digital transformation strategy aligned with organizational objectives
• Provide visionary leadership and set strategic direction for IT, Business Applications, and the AI & Automation CoE
• Champion a culture of innovation, continuous improvement, and operational excellence
• Identify, prioritize, and oversee implementation of AI and automation solutions for process improvement and operational efficiency
• Ensure continuous enhancement of AI tools, frameworks, and automation practices
• Foster upskilling of staff and organization-wide adoption of transformative technologies
• Direct IT infrastructure management; optimize mission-critical business applications and SaaS portfolio performance
• Oversee effective integration of digital tools with legacy systems, ensuring seamless business operations
• Build and manage strong relationships with executive leadership and cross-functional teams (GTM, Finance, Marketing, HR, Engineering)
• Lead change management efforts and engage stakeholders to maximize digital adoption and impact
• Continuously research and pilot emerging technologies and industry trends
• Promote experimentation, rapid scaling of innovation, and continuous learning across the organization

Benefits

• Technology stipend for new employees
• Monthly cell phone and internet stipend
• Health and wellness benefit
• In-office catered lunches (where applicable) and monthly Grubhub credit
• Company and team events
• Flexible time off and volunteer time off
• Stock options
• Comprehensive health benefits (medical, dental, vision)
• 401(k) retirement plan
• Stock options
• Flexible paid time off
• 14 weeks of fully-paid gender-neutral parental leave
• Fertility and adoption assistance
• Mental health counseling
• 401(k) retirement plan
• Rich health insurance offerings—including medical, dental, vision and life and disability insurance