IT Lead

SimplePractice

11h•$135,978 - $169,973

About The Position

SimplePractice is seeking a Lead IT Support Engineer to drive enterprise IT operations, lead strategic infrastructure initiatives, and mentor a growing team of support engineers. The role bridges technical execution and strategic business goals by helping architect scalable systems and improve internal service delivery. A primary focus is leading the company’s internal AI adoption initiative, including rollout, administration, governance, and vendor ecosystem management for AI productivity tools. Reporting to the Senior IT Manager, the role owns complex project roadmaps, establishes operational standards, and mentors junior IT Support Engineers. It is structured for someone aiming to transition into a formal IT Manager role with direct reports as the department expands. The position divides time between leading enterprise-wide IT initiatives and mentoring (50%), and architecting, automating, and maintaining resilient IT infrastructure, handling complex escalations, and managing vendors and licensing (50%). It includes an on-call schedule to support team members during off-hours and weekends, including one weekend day every two weeks.

Requirements

High school diploma or equivalent, or a higher degree.
At least 7 years of progressive IT experience, including senior, technical lead, or mentoring responsibilities in a fast-growing enterprise environment.
Deep administrative expertise in Okta, Jamf or similar MDMs, Google Workspace Enterprise, Zoom Admin, Slack Enterprise, and automated Identity Lifecycle Management solutions.
Familiarity with enterprise AI tooling environments, API key management, consumption- or token-based licensing models, and enterprise AI security considerations.
Experience evaluating vendor tools, managing SaaS license pools, and collaborating with Procurement on contract negotiations and renewals.
Ability to coach, mentor, and develop IT Support Engineers, with aptitude and interest in progressing into formal IT management with direct reports.
Practical experience in regulated environments requiring HIPAA, SOC 2, or NIST compliance controls.
Strong technical troubleshooting skills and a business-first mindset, including the ability to turn operational pain points into scalable technical solutions under pressure.
Exceptional written and verbal communication skills and expertise creating documentation, workflows, and playbooks in Notion or similar enterprise wikis.
A proactive, high-energy, collaborative leadership style, with empathy, clarity, and accountability.

Responsibilities

Lead enterprise-wide IT initiatives, including the enterprise AI adoption initiative, and partner with cross-functional leaders to align IT strategy with business growth.
Mentor junior and mid-level IT Support Engineers in their day-to-day work.
Architect, automate, and maintain resilient IT infrastructure; oversee complex escalations; and manage vendor relationships and licensing models.
Lead deployment, access provisioning, security controls, and administration for tokenized and consumption-based AI tools, including Claude, Cursor, OpenAI, Notion AI, and Gemini.
Partner with internal teams to track AI consumption metrics, optimize token usage, and evaluate emerging AI solutions.
Work with Procurement on contract negotiations, license management, and vendor relationships for enterprise software, hardware, and AI providers.
Architect, engineer, and implement internal enterprise technology solutions that promote self-service, reduce operational friction, and scale productivity.
Lead the design and continuous audit of internal IT controls to support adherence to HIPAA, SOC 2, and enterprise security frameworks across systems, devices, and AI integrations.
Design, implement, and optimize Single Sign-On (Okta), SCIM, and software integrations across the enterprise SaaS stack.
Oversee knowledge management in Notion, including advanced playbooks, standard operating procedures, AI usage guidelines, and technical onboarding programs.
Serve as the senior escalation point for complex Tier 3 technical issues and conduct root cause analysis to prevent recurring incidents.
Manage enterprise endpoint management platforms such as Jamf or similar MDMs, including deployment standards, patch management, and hardware lifecycle strategies.
Help build operational workflows and onboarding practices that scale with the IT team and company.
Participate in an on-call schedule covering off-hours and weekends, including one weekend day every two weeks.