Head of AI Transformation

simplepractice55; United States; Remote; USD 250,000 - 315,000; Full time

Benefits offered by this job

Medical, dental, vision, life, and dis

Disability insurance

401(k) plan with company match

Flexible Time Off

Wellbeing days

Paid holidays

Summer Fridays

Mental health resources

Parental leave with backup care

Tuition reimbursement

Employee Resource Groups

Job summary

SimplePractice is seeking a Head of AI Transformation to lead internal AI adoption across GTM and admin functions. You will build a small team of AI solution engineers embedded with business domains and drive velocity and quality while safeguarding customer data in a regulated environment.

The role blends technology strategy with change management and requires a strong track record in cross-functional leadership within B2B SaaS and healthcare-adjacent spaces.

Qualifications

• Proven leadership in AI strategy and transformation.
• Track record directing data and knowledge-architecture decisions.
• Cross-functional change leadership across organisations.
• Experience in regulated environments with security focus.
• Hands-on experience in B2B SaaS serving small businesses.

Responsibilities

• Define the vision, goals, and roadmap for internal AI adoption in partnership with company leadership.
• Build, lead, and manage a team of AI solution engineers delivering the transformation roadmap.
• Set and update KPIs and OKRs for internal AI adoption and lead AI platform initiatives.
• Translate advances in AI into refreshed strategy and execution plans.
• Educate and evangelize AI across the organization with demos and use cases.
• Collaborate with Technology and IT to ensure secure, responsible data use.

Skills

AI strategy

Team leadership

Change management

B2B SaaS

Data security

Cross-functional leadership

Job description

Role overview

A healthcare technology company that supports independent health and wellness practitioners is hiring a Head of AI Transformation to lead internal AI adoption across its go-to-market and general/administrative functions. This senior leadership role blends technology strategy with change management, building a small team of AI solution engineers that embed with business domains such as marketing. The mission is to increase organizational velocity and quality by applying AI thoughtfully, while protecting customer data privacy and security in a regulated environment.

Responsibilities

• Define the vision, goals, and roadmap for internal AI adoption in partnership with company leadership, grounding decisions in a Jobs-To-Be-Done framework
• Build, lead, and manage a team of AI solution engineers, owning delivery against the AI transformation roadmap
• Set and update KPIs and OKRs for internal AI adoption and lead specific projects on the AI Internal Platform track
• Translate the latest advances in AI into refreshed strategy and execution plans as the technology evolves
• Evangelize AI across the organization through education, demos, and example use cases, listening to and addressing adoption concerns
• Collaborate with Technology and IT teams to align on shared foundational tooling and ensure responsible, secure use of data

Requirements

• Significant technology leadership experience with a strong, fact-based point of view on where AI is headed
• Technical background sufficient to direct data and knowledge-layer architecture decisions
• Demonstrated track record of cross-company and cross-functional change leadership
• Enthusiasm for AI paired with pragmatic, value-driven judgment
• Hands-on experience inside B2B SaaS companies serving small business customers
• Experience in regulated environments such as healthcare, with a security-first mindset and a focus on customer trust

Nice to have

• Background applying AI inside marketing, sales, or other GTM functions
• Experience embedding engineers into non-technical business teams as solution partners

Benefits and work setup

• Competitive benefits package including medical, dental, vision, life, and disability insurance
• 401(k) plan with company match
• Flexible Time Off, wellbeing days, paid holidays, and summer Fridays
• Mental health resources and paid parental leave with backup care
• Tuition reimbursement and Employee Resource Groups
• Annual bonus or commission eligibility may apply; some roles include overtime pay
• Expected annual base compensation range of $250,000–$315,000 USD, depending on skills, experience, qualifications, and location