Director, Information Technology

Hopscotch Primary Care • Chicago, IL

14h • $150,000 - $190,000

About The Position

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.

Requirements

• 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.

Nice To Haves

• 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).

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.

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: Associate degree