Head of Digital Transformation

We are seeking a strategic, collaborative, and user-centered leader to serve as Head of Digital Transformation within our technology and operations organization. The successful candidate will define and drive a multi-year digital transformation roadmap that modernizes systems and processes, strengthens cross-functional capabilities, and delivers measurable business outcomes. This role requires strong strategic vision, experience leading enterprise-scale change programs, fluency with modern digital platforms and data practices, and an emphasis on user experience and measurable value.

Key Responsibilities - Strategy & Transformation

• Develop and own the organization’s digital transformation strategy and roadmap, aligning initiatives with business priorities, industry trends, and customer needs.

• Lead cross-functional planning to identify opportunities for modernization across product, engineering, operations, marketing, and customer success, prioritizing initiatives based on impact, risk, and cost.

• Establish governance, decision-making frameworks, and metrics to evaluate program progress and ensure accountability across stakeholders and vendors.

• Design and implement scalable, user-focused digital products, platforms, and workflows that improve efficiency, customer experience, and data-driven decision making.

• Champion adoption of modern technology stacks, cloud services, APIs, integration patterns, and automation tools while balancing security, compliance, and cost considerations.

• Collaborate closely with design, product management, data & analytics, security, and IT teams to translate business requirements into technical solutions and user journeys.

• Drive organizational change management, including stakeholder engagement, training programs, communications, and role design to ensure durable adoption of new ways of working.

• Manage relationships with external partners, systems integrators, and vendors; develop scopes of work, assess proposals, and oversee delivery to quality, budget, and timeline targets.

• Define and track KPIs—such as time to market, cost to serve, customer satisfaction, uptime, and process cycle time—to measure transformation outcomes and guide continuous improvement.

• Prepare executive briefings, progress reports, and business case materials to secure funding and maintain leadership alignment.

Required Qualifications - Skills & Experience

• Bachelor’s degree in Business, Computer Science, Information Systems, or a related field, or equivalent practical experience.

• Minimum 8–12 years of progressive experience leading digital programs, product or platform teams, enterprise transformation, or management consulting engagements.

• Proven track record delivering complex, cross-functional transformation initiatives that produced measurable improvements in cost, speed, or customer outcomes.

• Strong strategic thinking with the ability to translate vision into pragmatic roadmaps, priorities, and deliverables.

• Technical fluency with cloud platforms, API-driven architectures, data platforms, SaaS solutions, and automation tooling; ability to partner effectively with engineering and operations teams.

• Experience with change management, stakeholder engagement, and building organizational capabilities to sustain digital initiatives.

• Excellent communication and interpersonal skills, including experience presenting to executives and leading interdisciplinary teams.

• Data-driven mindset with experience defining KPIs, using analytics to guide decisions, and driving continuous improvement.

Preferred Qualifications - Domain & Tools

• Experience with agile delivery models, product management practices, and platform-oriented operating models.

• Familiarity with cloud providers (e.g., AWS, Azure, GCP), integration platforms, modern data stack components, and CI/CD pipelines.

• Knowledge of information security, privacy frameworks, and regulatory requirements relevant to our sector.

• Experience managing vendor relationships and large third‑party implementations, including procurement, contracts, and SLAs.

• Advanced degree or certifications in project/program management, cloud, or change management (e.g., PMP, AWS/GCP certifications, Prosci) is a plus.

Work Environment & Compensation

• Full-time position with a collaborative, cross-functional work model; onsite presence is expected with opportunities for flexible scheduling as appropriate.

• Competitive salary and benefits package commensurate with experience, including health coverage, retirement plan options, paid time off, and professional development support.

• Opportunities for training, certification reimbursement, and career progression within a mission-driven and inclusive technology organization.

• We are committed to diversity, equity, and inclusion and foster a respectful work environment that supports work-life balance, employee well-being, and ethical conduct.