ABOUT THE ROLE

Hopscotch Primary Care is looking for an experienced and strategic Director of IT. The ideal candidate will develop a deep understanding of the business, our strategy and the technical needs across teams. They will be responsible for overseeing all aspects of our IT department, ensuring the alignment of technology initiatives with our business objectives.If you’re excited by the opportunity to shape the future of healthcare in rural and small-town communities and enjoy solving difficult problems in a fast-moving environment, we’d love to hear from you.

RESPONSIBILITIES 

Lead technology strategy

• Develop and maintain the multi-year technology roadmap spanning infrastructure, security, and IT operations, maintaining alignment with the business strategy and needs.
• Set and manage the annual technology budget across IT and security, balancing build, buy, and partner decisions.
• Translate technical strategy for executive and non-technical stakeholders, communicating security and IT direction in clear, accessible terms, and using data to influence decisions toward the best outcome for the business.
• Own strategic vendor and partner relationships across cloud, security, and clinical-systems providers, negotiating commercial and technical terms. This includes the electronic health record deployment and maintenance.

Own enterprise infrastructure, security, and compliance

• Own overall IT infrastructure and software systems - including SaaS platforms, identity, collaboration tooling, and data flows between them.
• Lead the enterprise security program end-to-end. Accountable for policy, controls, risk posture, and incident response, with authority to set direction and enforce standards.
• Own HIPAA and PCI compliance across the technology stack. Accountable for continuous compliance, audit readiness, and timely remediation of any gaps.
• Set and enforce enterprise policy including disaster recovery, backup and retention, and acceptable AI use.
• Own system lifecycle planning driving platform modernization, legacy sunset, and continuous improvement of enterprise knowledge management.
• Establish the AI safety, governance, and responsible-use posture spanning data handling, model access, evaluation gates, and approval pathways, with accountability mechanisms that hold teams to the standard.
• Partner with product & engineering to review, secure, and operate the internal-facing systems and tools they build, holding them to consistent standards for access control, reliability, and supportability.

Scale clinic and corporate IT operations

• Own the technical buildout of new and acquired clinics. Accountable for network, endpoint, security, and clinical-system readiness from evaluation through go-live.
• Own IT lifecycle management for corporate and clinic hardware and software including procurement strategy, deployment, refresh, and decommissioning across the fleet.
• Lead the central and market IT operations team. Ensure responsive, high-quality support to clinicians, care teams, and central staff.
• Define, track, and manage to operational metrics for IT and AI services including availability, response times, adoption, and cost, driving measurable improvement against clear targets.

ABOUT YOU:

• Strategic and business-oriented with the ability to articulate business needs, scope solutions and clearly communicate value, tradeoffs and timing.
• Data-informed and decisive - confident making hard prioritization and tradeoff decisions using a mix of qualitative insights, quantitative data, KPIs and expected business impact.
• Experienced leading cross-functional initiatives; able to interface with stakeholders, structure work, manage dependencies and maintain momentum amid frequent context switching.
• A clear and compelling communicator; able to articulate the strategy and value of the tactical roadmap items to audiences ranging from technical peers to executive leadership.
• Self-aware and resilient, able to recognize missteps, learn from execution failures and re-engage with confidence and a bias toward action.

From a cultural perspective, you are:

• Accountable. You hold a high standard and you expect it from others too.
• Someone who treats mistakes as data. You move fast, name what isn't working, fix it, and carry the lesson forward.
• Customer-obsessed. You build genuine empathy with users, dig into what they actually need, and stay focused on solving real problems.
• A problem-solver, not a finger-pointer. You own challenges alongside your teammates - no blame, no deflection, just shared accountability for finding the way forward.
• A contributor who shapes the answer. You bring your strengths and perspective to every conversation because rigorous debate is how the strongest solutions get built.
• Comfortable with uncertainty. The plan will change and the priorities will shift - you make smart calls with what you have and course-correct with good judgement when things evolve.

Background

• 10+ years of progressive experience in technology leadership, including IT, infrastructure, security, or applied AI / software engineering with at least some of that time leading teams.
• Operating familiarity with healthcare-grade compliance (HIPAA, SOC 2, PCI), modern SaaS administration (Google Workspace or Microsoft 365, identity, security), and cloud infrastructure.
• Degree in computer science, engineering, a related technical discipline preferred or equivalent experience.

ADDITIONAL QUALIFICATIONS

• Experience leading IT, security, or platform engineering for a regulated industry (healthcare strongly preferred).
• Strong programming foundation preferred; current or recent proficiency in Python or TypeScript and comfort using AI-assisted development tools (Cursor, Copilot, Claude Code) as part of your own workflow.
• Experience with Azure or Google Cloud and the Microsoft 365 or Google Workspace stack at enterprise scale.
• Experience with athenahealth or other electronic health record.
• Experience with cyber-risk reduction strategies and security operations leadership (SOC/SIEM, identity, MXDR).

In accordance with the Illinois Pay Transparency Act, we’re providing the full salary range for this position. Actual compensation will be determined based on location, relevant experience and qualifications. Most offers will fall within a portion of the listed range. This position has a salary range of $150,000 – $190,000 annually, based on location, relevant experience and qualifications. In addition to base salary, we offer a comprehensive benefits package that includes:

• Paid holidays + PTO
• Company sponsored medical, dental, and vision insurance for you + your family
• FREE short-term and long-term disability insurance
• FREE $100k life insurance policy
• 401k plan with 4% company match + no vesting period
• $720 - $1,000 added to employee Health Savings Account annually for eligible health plans
• And more!

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