We are seeking a Senior Director, Digital Strategy to expand Bounteous’ work across Health Systems, Life Sciences, and B2B organizations. This role is responsible for shaping and closing enterprise digital transformation engagements across digital experience, data and AI, and marketing technology. The ideal candidate brings a track record of leading and selling complex strategy-led programs within healthcare and regulated B2B environments.
The Senior Director will partner with business, marketing, and technology leaders to position Bounteous’ capabilities across Digital Experience, Data & AI, Cloud, and Digital Engineering. This is a consultative, market-facing role focused on defining transformation roadmaps, aligning initiatives to business outcomes, and guiding clients through execution.
This leader will drive new client relationships, expand strategic accounts, and support growth across Bounteous’ Health+ and B2B portfolio.
Information Security Responsibilities
- 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
Role & Responsibilities
Serve as a trusted advisor to C-suite executives, shaping enterprise transformation agendas across digital experience, data, AI, and marketing technology.
Define and lead multi-year digital transformation strategies, aligning business objectives with scalable technology, operating models, and measurable outcomes.
Lead and contribute to $6M–$8M in annual pre-sales revenue, shaping complex pursuits, defining solution strategy, and driving account expansion.
Act as an executive strategist across key client engagements, ensuring alignment between business goals, solution approach, and delivery execution.
Partner with Solutioning, Client Service, and Delivery leadership to ensure seamless execution of transformation programs, maintaining strategic alignment across all phases of work.
Provide executive oversight across engagements, driving quality, velocity, and accountability across complex, multi-workstream programs.
Establish and evolve a point of view on AI enablement in healthcare, including use cases across operations, marketing, and organizational design, and translate this into actionable client strategies.
Lead industry-specific strategy development, including:
Commercialization of healthcare and life sciences offerings
Member/patient engagement, acquisition, and retention strategies
Digital front door and omnichannel experience transformation
Bottom-line growth modeling, aligning transformation initiatives to client EBIT and measurable financial outcomes
Influence and mentor cross-functional teams across strategy, solutioning, and delivery, leading through expertise and collaboration rather than direct reporting lines.
Collaborate with practice and competency leaders to ensure alignment of capabilities, talent, and delivery models to support client and market needs.
Contribute to the development of Health+ go-to-market offerings, industry frameworks, and strategic partnerships.
Represent Bounteous externally as a thought leader in healthcare digital transformation, supporting market positioning and industry presence.
Preferred Qualifications
15+ years of experience in digital strategy, consulting, or client leadership roles within healthcare, life sciences, or related industries.
Deep expertise within the U.S. healthcare ecosystem, including payer, provider, and/or life sciences organizations at enterprise scale.
Proven track record of leading enterprise digital transformation strategy, including roadmap development and execution across people, process, data, and technology.
Strong understanding of marketing technology, digital experience platforms, and data ecosystems, including Adobe, Salesforce, and CDP solutions.
Demonstrated leadership in AI-enabled transformation, with experience defining and operationalizing use cases across healthcare organizations.
Experience developing commercial and growth strategies within healthcare, including patient/member engagement and retention.
Strong financial acumen, with experience connecting digital transformation initiatives to business value, ROI, and EBIT impact.
Experience operating within global delivery models, influencing distributed teams across regions to deliver complex programs at scale.
Exceptional executive presence with the ability to influence C-suite stakeholders and drive strategic decision-making.
Proven success in business development and strategic pursuits, including complex, multi-million-dollar opportunities.
Ability to lead through influence, mentorship, and cross-functional collaboration in a matrixed organization.
Client Engagement & Travel: Willingness to travel 50% or more to support executive client engagement, strategic workshops, and business development activities.
Bachelor’s degree in business, technology, or related field; advanced degree preferred.
Top Skills
Bounteous Calgary, Alberta, CAN Office
1215 13 Street Southeast. Suite 212, Calgary, Alberta, Canada, T2G 3J4
