Director of Strategy & Systems

HEALTHWORKS MEDICAL LLC • Paducah, KY

76d • Onsite

About The Position

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.

Requirements

• 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
• Comfort operating in regulated environments with security and compliance requirements
• 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

Nice To Haves

• Healthcare, occupational health, or multi-site services experience strongly preferred

Responsibilities

• 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
• 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
• 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
• 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, and 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
• Lead cross-functional planning for major initiatives, launches, and strategic programs
• Ensure initiatives are launched with defined processes, clear decision rights, and system and reporting readiness
• Serve as a strategic thought partner to the Director of Operations and Director of Future Operations
• Facilitate clean handoffs between design, pilot, and steady-state execution
• 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

Benefits

• Comprehensive benefits package including health benefits, paid time off, and retirement options
• Ongoing leadership and professional development support

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Number of Employees: 251-500 employees