Director of Strategy & Systems

The Director of Strategy & Systems is responsible for architecting aligning and governing the enterprise operating system of HealthWorks Medical. This role owns strategy execution process architecture and information technology strategy ensuring that systems workflows data and technology enable scalable reliable growth.

This role serves as the single point of accountability for enterprise systems design translating business and clinical needs into clear operating models technology roadmaps and execution plans while partnering with internal leaders and external vendors to enable delivery.

This position does not require hands-on software engineering expertise but it does require above-average IT systems and data acumen strong vendor leadership skills and the ability to guide modern technology and AI adoption in a regulated healthcare environment.

Core Responsibilities

1. Enterprise Strategy Execution

• Translate HealthWorks long-term strategic priorities into clear executable operating plans
• Own the enterprise strategy execution roadmap and planning cadence (annual quarterly rolling initiatives)
• Support executive leadership in prioritizing initiatives based on capacity readiness risk and return
• Ensure strategic initiatives are launched with appropriate process system and reporting readiness
• Align cross-functional leaders around shared priorities and execution frameworks

2. IT Strategy & Technology Governance (Explicit Ownership)

• Own the enterprise IT and technology strategy for HealthWorks Medical
• Develop and maintain a multi-year technology roadmap aligned to business clinical and operational goals
• Serve as the primary business owner for all internal platforms systems and integrations
• Oversee proprietary in-house application development in partnership with approved third-party development partners
• Define standards for system architecture interoperability data flow security posture scalability and reliability
• Partner closely with HealthWorks managed service provider (MSP) cybersecurity and compliance partners to:
  • Enable secure reliable and compliant IT operations
  • Support infrastructure access management monitoring incident response and data protection
  • Ensure alignment between strategic technology direction and operational execution
• Translate business and operational needs into clear technical requirements for MSPs developers and vendors
• Evaluate select and govern third-party technology platforms tools and partners
• Ensure technology investments deliver measurable operational financial and strategic value
• Reduce technical debt system sprawl and reliance on manual workarounds

This role owns technology direction priorities and governance while execution is enabled through internal teams and external partners.

3. AI Strategy & Intelligent Enablement

• Own HealthWorks AI strategy and roadmap aligned to operational efficiency clinical support analytics and decision-making
• Identify evaluate and prioritize AI use cases across operations clinical workflows reporting and administrative functions
• Partner with leaders and vendors to responsibly integrate AI into systems and processes
• Establish guardrails for ethical use data security compliance and scalability of AI solutions
• Ensure AI initiatives are practical value-driven and integrated into existing workflows not siloed experiments

4. Process Architecture & Playbook Governance

• Design and maintain HealthWorks end-to-end enterprise process architecture
• Own and govern the HealthWorks Process Playbooks ensuring:
  • Consistent structure and documentation standards
  • Clear ownership and accountability
  • Ongoing updates as the organization evolves
• Identify process gaps redundancies and friction points across functions
• Partner with functional leaders to simplify standardize and scale workflows
• Ensure processes and systems evolve together not independently

5. Cross-Functional Planning & Enablement

• Lead cross-functional planning for major initiatives launches and strategic programs
• Ensure initiatives are launched with:
  • Defined processes
  • Clear decision rights
  • System and reporting readiness
• Serve as a strategic thought partner to:
  • Director of Operations (todays execution)
  • Director of Future Operations (tomorrows growth)
• Facilitate clean handoffs between design pilot and steady-state execution

6. Organizational Design & Readiness

• Partner with executive leadership and HR to support future-state organizational design
• Identify capability gaps system constraints and readiness risks tied to growth
• Support leadership clarity by defining decision rights roles and accountability structures
• Ensure organizational complexity scales intentionally not reactively

What This Role Is Not

• Does not manage day-to-day clinic or site operations
• Does not own frontline performance or staffing execution
• Does not act as a project manager for routine operational work
• Does not serve as a hands-on IT engineer or developer

This role focuses on system design strategic alignment and enablement not execution.

Key Outcomes & Measures of Success

• Clear repeatable enterprise processes across all major functions
• Strategic initiatives launched without operational disruption
• Technology investments aligned to business value
• Reduced operational friction rework and workarounds
• Scalable secure and well-governed IT and application ecosystem
• Practical AI adoption embedded into workflows
• Leadership teams operating from shared systems playbooks and data

Why This Role Matters

As HealthWorks Medical grows complexity will increase faster than headcount. The Director of Strategy & Systems ensures growth remains intentional scalable and secure aligning people process technology and AI so the organization can scale without friction.

***Optional Video Submission (Strongly Encouraged)***

Candidates are invited to submit a short (23 minute) video in lieu of or in addition to a traditional cover letter.

In this video please briefly address the following:

1. An example of an operating system process architecture or enterprise framework you designed or materially improved
2. How you translated business strategy into systems technology or process improvements
3. How you led cross-functional change without direct authority

If you choose to submit a video please email a link (Loom Google Drive Vimeo etc.) directly to with the subject line:

Director of Strategy & Systems Video Submission Your Name

Qualifications & Experience

• 8 years of experience in strategy operations systems design IT governance or organizational development
• Demonstrated experience designing scalable operating models and enterprise systems
• Above-average IT and systems literacy (architecture integrations data flow vendor management)
• Experience leading cross-functional initiatives without direct authority
• Healthcare occupational health or multi-site services experience strongly preferred
• Comfort operating in regulated environments with security and compliance requirements

Leadership Attributes

• Enterprise mindset with strong judgment and discretion
• Systems thinker who balances structure with adaptability
• Ability to influence and align leaders without direct control
• Clear communicator with strong written and executive presence
• Service-oriented leader focused on enabling others success

Compensation & Benefits

• Base Salary: Competitive commensurate with experience and scope; expected range $120000 $155000 annually
• Performance Incentive: Eligibility for an annual performance bonus tied to individual performance strategic milestones and company results
• Benefits: Comprehensive benefits package including health benefits paid time off and retirement options
• Professional Development: Ongoing leadership and professional development support

Compensation will be aligned with experience demonstrated capability and long-term potential within HealthWorks Medical.