Director / Sr. Director, Digital Strategy (Healthcare)

Bounteous is a global AI Services firm where agentic engineering and human experience converge to deliver transformative business outcomes for the enterprise. We help organizations design, build, and scale AI-driven products, platforms, and processes. With more than 5,000 team members worldwide, Bounteous delivers AI that sticks, powering adoption and outcomes that move organizations from experimentation to true transformation. Bounteous is backed by New Mountain Capital, a New York-based growth-oriented investment firm that emphasizes business building.

We are seeking a Director/Sr. Director, Digital Strategy to lead high-impact digital and AI-enabled transformation engagements for leading healthcare accounts.

This role is a senior client-facing leader, partnering with C-suite and senior stakeholders to shape enterprise digital and AI strategy, leading multidisciplinary teams of consultants and digital practitioners, and translating strategy into new operating models and measurable business outcomes. You will also play a key role in business development, partnering with the Growth team to identify, scope, and win new business.

• Promote and enforce awareness of key information security practices, including acceptable use of information assets, malware protection, and password security protocols
• Identify, assess, and report security risks, focusing on how these risks impact the confidentiality, integrity, and availability of information assets
• Understand and evaluate how data is stored, processed, or transmitted, ensuring compliance with data privacy and protection standards (GDPR, CCPA, etc.)
• Ensure data protection measures are integrated throughout the information lifecycle to safeguard sensitive information

• Serve as a trusted advisor to senior client executives, including C-suite stakeholders, shaping digital and AI-enabled transformation agendas.

• Lead and contribute to pre-sales activity, defining solution strategy for complex pursuits and expanding strategic accounts.

• Lead multidisciplinary teams of consultants and digital practitioners in developing and executing digital and AI strategies that create competitive advantage and measurable value for clients.

• Clarify and define ambiguous or complex business challenges, objectives, and goals.

• Partner with cross-functional teams to gather and analyze customer, market, and business insights, identifying opportunities for innovation.

• Lead assessments of clients' digital capabilities and AI maturity to inform strategic recommendations.

• Design and facilitate workshops and stakeholder interviews with senior client leadership, in person and virtually.

• Define the business vision, strategy, and roadmap for digital and AI-enabled transformation, connecting technology capability to organizational readiness, role redesign, and new ways of working.

• Conduct analysis and financial modeling to validate business viability and build the business case for change, connecting transformation initiatives to business value.

• Develop and present strategic recommendations, roadmaps, and plans to client leadership, gaining alignment on next steps.

• Design stakeholder engagement, communication, and change management strategies tailored to executive, operational, and frontline audiences.

• Actively contribute to firm growth by identifying new business opportunities, designing engagement approaches, scoping and estimating work, preparing proposals, and delivering pitch presentations.

• Advance the digital strategy practice by developing consulting frameworks, methodologies, and thought leadership.

• Mentor and develop junior team members, fostering their professional growth.

• 8+ years of experience in digital strategy, management consulting, or technology transformation consulting; candidates with 12+ years and enterprise-scale leadership will be considered for the Sr. Director level.

• Proven track record leading enterprise digital transformation strategy, including roadmap development and execution across people, process, data, and technology.

• Experience developing target operating models, role redesigns, and governance frameworks in the context of AI/technology adoption.

• Strong financial acumen, with experience connecting transformation initiatives and adoption outcomes to business value.

• Exceptional executive presence with the ability to influence C-suite and senior stakeholders, navigate complex organizations, and lead through ambiguity.

• Proven success in business development and strategic pursuits.

• Ability to lead through influence, mentorship, and cross-functional collaboration in a matrixed, global organization.

• Proficiency in customer research methods, journey mapping, service blueprints, ecosystem mapping, and prototyping.

• Excellent verbal and written communication skills.

• Willingness to travel 30–50% to support executive client engagement, strategic workshops, and business development activities.

• Bachelor's degree required; advanced degree (e.g., MBA) preferred.

$135,000 - $165,000 a year

Individual pay is determined by many factors, including experience, relevant education or training, and organizational needs. The mid-range to maximum of the salary range is generally reserved for individuals who are highly experienced in the role.

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Bounteous is proud to be an equal opportunity employer. Bounteous does not discriminate on the basis of race, religion, color, sex, gender identity, sexual orientation, age, physical or mental disability, national origin, veteran status, or any other status protected under federal, state, or local law. Bounteous is willing to sponsor eligible candidates for employment visas.

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