Lead IT Support Engineer

About Us

At SimplePractice, we are improving access to quality care by equipping health and wellness clinicians with all the tools they need to thrive in private practice. 

More than 250,000 providers trust SimplePractice to build their business through our industry-leading software with powerful tools that simplify every part of practice management. From admin work to clinical care, our suite of innovative solutions work together to reduce administrative burden—empowering solo and small group practitioners to thrive alongside their clients. 

Award-winning and people-first, SimplePractice is shaping the future of health tech. Recognized by MedTech Breakthrough, the Digital Health Awards, and BuiltIn's Best Places to Work.

Our Culture

At SimplePractice, culture is our foundation. It influences the way we work, how we serve our customers, and how we approach accomplishing our mission. We have five core values that we strive to embody every day:

• We think big
• We take simplicity seriously
• We come as we are
• We act with humility
• We are built on trust

Culture is everyone’s responsibility at SimplePractice. Our culture is what drives us to do better for our teammates and customers.

Connection and collaboration are also key to our success. You will work with our talented multi-national teams and have opportunities to participate in onsites in both the US and Mexico.

The Role

SimplePractice is the future of practice management. We’re at the forefront of making it simple for clinicians to run and grow their practices. We’ve built the highest-rated practice management software and we’re on track to become the market leader. 

We are looking for a Lead IT Support Engineer to drive our enterprise IT operations, lead strategic infrastructure initiatives, and mentor a growing team of support engineers. In this high-impact role, you will act as a bridge between technical execution and strategic business goals, helping architect scalable systems and elevate internal service delivery.

A primary focus for this role will be spearheading our Internal AI Adoption initiative which is a high-priority upcoming enterprise project. As our IT department expands, you will lead the rollout, administration, governance, and vendor ecosystem for next-generation AI productivity tools.

Reporting directly to the Senior IT Manager, you will hold a key leadership role within a growing department by taking ownership of complex project roadmaps, establishing operational standards, and mentoring junior IT Support Engineers. This position is explicitly structured for a candidate aiming to transition into a formal IT Manager role with direct reports as the department expands in the future.

Responsibilities

• As a Lead IT Support Engineer, your core responsibilities include: 
• 50% of your time leading enterprise-wide IT initiatives, like our enterprise AI adoption initiative, partnering with cross-functional leadership to align IT strategy with business growth, and mentoring junior and mid-level IT Support Engineers through their day-to-day work.
• 50% of your time architecting, automating, and maintaining resilient IT infrastructure, overseeing complex escalations, and managing key vendor relationships and licensing models.  
• Lead the technical deployment, access provisioning, security controls, and admin management for tokenized and consumption-based AI tools across the organization (e.g., Claude, Cursor, OpenAI, Notion AI, Gemini).
• Partner with internal teams to track consumption metrics, optimize token usage, and evaluate emerging AI solutions to enhance productivity across all business functions.
• Work closely with Procurement on contract negotiations, license management, and vendor relationships for enterprise software, hardware, and AI providers.
• Architect, engineer, and implement internal enterprise tech solutions that promote self-service, reduce operational friction, and scale productivity across a growing team.
• Lead the design and continuous audit of internal IT controls to guarantee strict adherence to HIPAA, SOC 2, and enterprise security frameworks across all systems, devices, and AI integrations.
• Design, implement, and optimize Single Sign-On (Okta), SCIM, and complex software integrations across our enterprise SaaS tech stack.
• Oversee the department's knowledge management framework in Notion, authoring advanced playbooks, standard operating procedures (SOPs), AI usage guidelines, and technical onboarding programs.
• Serve as the senior point of escalation for complex, Tier 3 technical issues, conducting root cause analysis (RCA) to prevent recurring incidents across internal tools and infrastructure.
• Manage enterprise endpoint management platforms (Jamf or similar MDMs), establishing deployment standards, patch management strategies, and hardware lifecycle strategies.
• Help build operational workflows and onboarding practices designed to scale as the IT team and company continue to grow.
• On-call schedule to support our team members during off hours and weekends (1 weekend day every 2 weeks).

Desired Skills & Experience

• High school diploma (or equivalent) or higher degree 
• 7+ years of progressive IT experience, with demonstrated experience acting in a senior, tech lead, or mentor capacity within a fast-growing enterprise environment.
• Deep administrative expertise in Okta (Identity & Access Management), Jamf (or similar MDMs), Google Workspace Enterprise, Zoom Admin, Slack Enterprise, and automated Identity Lifecycle Management solutions.
• Familiarity with deploying and managing enterprise AI tooling environments (e.g., OpenAI, Claude, Cursor, Notion AI, Gemini), including understanding API key management, consumption/token-based licensing models, and enterprise security considerations for AI.
• Experience evaluating vendor tools, managing SaaS license pools, and collaborating with Procurement on contract negotiations and renewals.
• Proven ability to coach, mentor, and elevate the technical capabilities of fellow IT Support Engineers, with a strong desire and aptitude to step into a formal IT Management role with direct reports as the department grows.
• Practical experience working in regulated environments requiring strict HIPAA, SOC 2, or NIST compliance controls.
• Superior technical troubleshooting capabilities combined with a business-first mindset—able to translate complex operational pain points into scalable technical solutions under pressure.
• Exceptional written and verbal communication skills, with expertise structuring documentation, workflows, and playbooks in Notion or similar enterprise wikis.
• A proactive, high-energy leader who thrives in a collaborative, scaling environment and approaches every challenge with empathy, clarity, and accountability.

Benefits

We offer a competitive benefits program including:

• Medical, dental, vision, life & disability insurance
• 401(k) plan with company match 
• Flexible Time Off (FTO), wellbeing days, paid holidays, and summer Fridays
• Mental health resources
• Paid parental leave & Backup Care
• Tuition reimbursement
• Employee Resource Groups (ERGs)

California Job Applicant Privacy Notice

Thank you for your interest in opportunities at SimplePractice LLC (“SimplePractice” or “us” or “we” or “our”). Please note that when you submit your resume or application materials to us for employment purposes, you are subject to the SimplePractice California Job Applicant Privacy Notice. 

For more information about our privacy practices, please contact us at [email protected].

Base salary is one component of total compensation. Employees may also be eligible for an annual bonus or commission. Some roles may also be eligible for overtime pay.

The amount below represents the expected annual base compensation range for this job requisition. Ultimately, in determining your pay, we’ll consider many factors including, but not limited to, skills, experience, qualifications, geographic location, and other job-related factors.

Base Compensation Range 122381 - 152976 USD