Director, Finance Transformation

About the role

You will define and execute the strategic vision for KAYAK's global finance systems landscape, ensuring every technology decision supports enterprise scalability and long-term business objectives. You own the end-to-end lifecycle of critical finance platforms, from initial discovery and requirements synthesis through implementation, optimization, and continuous improvement. This role is responsible for shaping how finance teams interact with technology on a daily basis, removing friction and enabling more insightful, efficient operations. You will be the central thought leader guiding the evolution of the finance tech stack across the entire organization. By focusing on outcomes over outputs, you ensure that systems deliver tangible value in speed, accuracy, and reliability. You will champion the adoption of emerging capabilities, embedding AI and automation into the core of financial workflows. Ultimately, your work will determine whether our technology stack becomes a strategic asset or a limiting constraint for the business.

Key facts

What you'll do

Define the enterprise architecture for finance systems, aligning product strategy with business goals to enable scalable, future-ready technology solutions.

Own the NetSuite ERP platform as the system of record, establishing standards for configuration, customization, and integration across Pontus, BlackLine, and FloQast.

Champion the multi-year finance systems roadmap, prioritizing initiatives that reduce close cycles, lower reconciliation risk, and strengthen data integrity.

Lead the development and execution of the finance AI and automation strategy, identifying high-impact opportunities across forecasting, variance analysis, and workforce planning.

Partner with Data Engineering to establish a trusted data foundation, ensuring data quality, accessibility, and governance before large-scale AI or ML applications are deployed.

Recruit, develop, and retain a high-performing team of Systems Analysts, Finance Systems Product Managers, and Solution Engineers, fostering a culture of psychological safety and continuous learning.

Translate complex finance transformation objectives into clear, phased delivery plans with defined milestones, owners, success criteria, and transparent scope management.

Manage capital and operating budgets for finance systems initiatives, building data-backed business cases to secure executive sponsorship from the CFO, CAO, and corporate controllers.

Serve as the primary subject matter expert for NetSuite governance, overseeing configuration control, upgrade management, and adherence to SOX requirements.

Represent Finance Systems in corporate architecture forums and data governance councils, promoting collaboration and innovation through demos, showcases, and automation hackathons.

Build and maintain strong partnerships with Accounting, Tax, Treasury, FP&A, Internal Audit, and Engineering to align systems strategy with enterprise priorities.

Develop and maintain an AI use-case registry to govern the full lifecycle of automation ideas, from initial discovery through implementation and eventual retirement.

Drive cultural change by creating internal moments for innovation, such as process improvement challenges, knowledge-sharing sessions, and cross-team collaboration.

Act as the key liaison between technical teams and senior finance leadership, translating business needs into clear requirements and technology roadmaps.

Requirements

Bring a minimum of 10 years of cumulative experience in finance systems, enterprise technology, or a closely related discipline, with a proven ability to deliver complex systems at scale.

Demonstrate hands-on experience with NetSuite ERP and a deep understanding of end-to-end finance processes, including Order-to-Cash, Procure-to-Pay, and Record-to-Report.

Show a clear history of leading cross-functional transformation initiatives, such as ERP migrations, payment system implementations, or major enhancements to financial reporting environments.

Have direct experience implementing AI-driven or automation-first solutions within finance or enterprise settings, including the ability to assess feasibility and measure impact.

Consistently build strong, trust-based relationships across a wide range of teams, navigating complex organizational environments with empathy and professionalism.

Communicate clearly and directly, both in writing and verbally, presenting structured recommendations and compelling narratives to senior leadership including the CFO and executive committee.

Adopt a proactive mindset, anticipating risks and opportunities, and driving the organization forward rather than reacting to problems after they emerge.

Hold a Bachelor's or advanced degree in Accounting, Engineering, Computer Science, Finance, or a related field that provides a strong foundation for technology leadership in finance.

Nice to have

Experience with corporate architecture frameworks and enterprise data governance principles.

Familiarity with AI model selection, prompt engineering, and responsible AI practices in financial contexts.

Background in managing global systems rollouts, including coordination across regions and regulatory considerations.

Practical notes

This role requires 3 days per week in our Norwalk, CT office.

Success in this role depends on the ability to influence stakeholders and manage multiple priorities in a fast-paced environment.