Head of AI Transformation

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

Benefits offered by this job

Medical Insurance

Dental Insurance

Vision Insurance

Life Insurance

Disability Insurance

401(k) with match

Flexible Time Off

Wellbeing days

Paid holidays

Summer Fridays

Mental health resources

Parental leave

Tuition reimbursement

ERGs

Job summary

SimplePractice LLC seeks a technical Head of AI Transformation to lead AI adoption across GTM and G&A. You will build a small team of AI solution engineers and bridge technology with domain experts in marketing and operations.

You will define strategy, roadmaps, and KPIs for AI adoption, partner with IT on shared infrastructure, and ensure data privacy and security as technology evolves. This senior IC leadership role aims to accelerate value for customers while aligning with existing roadmaps.

Qualifications

• 10+ years of technology leadership experience.
• Cross-functional leadership and change management.
• Experience in B2B SaaS serving small businesses.
• Background in regulated healthcare environments and security-minded culture.

Responsibilities

• Lead AI transformation across GTM and G&A functions.
• Build and lead a team of AI solution engineers.
• Define strategy, vision, and roadmaps for AI adoption.
• Collaborate with IT and Technology on shared infrastructure.
• Educate and evangelize AI across the company.

Skills

Technology leadership

Cross-functional leadership

AI enthusiasm

B2B SaaS

Healthcare/regulatory awareness

Tools

IT collaboration

Job description

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. In 2026, we were recognized by BuiltIn as a Best Remote Company to Work For, Software Guru’s Best Places to Code, Becker Healthcare Telehealth Companies to Know, and we won a MedTech Breakthrough Award for Best Practice Management Solution Provider.

The Role

At SimplePractice, we are embracing AI to improve our internal way of working - increasing velocity, quality and overall efficiency - allowing our people to focus on the most human areas of effort - working with other humans.

We believe that AI can fundamentally change how we do work - but it takes a deep connection between the domain (such as marketing) and the technology - especially when the technology is still evolving so quickly. It’s not enough to just adopt tools to make video creation faster, or to automate email campaigns, we need to start with what we need to accomplish - we like the Jobs To Be Done framework for this - and break down to first principles.

To lead the Technology side of this partnership, we are looking for a technical Head of AI Transformation that will drive the AI transformation efforts across the GTM and G&A functions at SimplePractice. This person will build a small team of AI solution engineers that will embed with functions such as Marketing - providing the bridge between technology and domain expertise.

This role will provide the leadership on the strategy and vision for AI adoption in these functions and work closely with the Technology and IT teams to share the foundational tooling to make AI effective. The hardest part of this role may be providing the vision on what is possible as the technology evolves and temper it with our responsibilities to our customers to ensure the privacy and security of their data - and then lead the rest of the company on this journey with you.

This is an opportunity to come in and lead AI transformation at a company at scale and be part of our mission to help independent private practices to thrive.

Responsibilities

In this role, you will drive the adoption of AI across the GTM and G&A functions at SimplePractice. The components of this are:

• Collaborate and drive consensus with the company leadership on what the vision and goals for AI Adoption are at SimplePractice
• Convert vision and goals to a concrete roadmap and execution plan
• Own delivery of that plan through building and leading a team of AI solution engineers.
• Bring in the latest AI advancements into the discussion and drive change to the vision/goals/plan as needed.
• Evangelize and educate the company on AI and specifically on AI for internal automation.
• Getting hands on with AI and these use cases.

You will own:

• The overall AI Internal Transformation roadmap
• Definition and updates to the KPIs and OKRs for Internal AI Adoption
• Direct management responsibility for the AI Solution Engineers.
• The methodology and framework for building new AI based tooling internally
• Define and lead specific project work in the AI Internal Platform track.

How will you do it

• We are a collaborative culture so bold changes like this require bringing people along for the journey. Education, demos, examples, and understanding concerns around AI adoption need to be heard and recognized by this leader.
• A small matrixed team of individuals will be the execution arm of this role but it will still require cross company coordination and alignment.
• We view AI adoption as critical for our success as a company by allowing us to move faster and deliver more value to our customers but also need to avoid disrupting our current customer base and roadmap. A fine balance to walk.
• This is primarily an Individual Contributor leadership role - your drive and passion will pull people with you - do not expect or require rigid top down mandates to achieve your goals - but we do have company level goals for adoption that will line the company behind you. But be prepared to be inspiring.
• You will partner with the IT and Technology teams on shared infrastructure - company context hub, harnesses and other enabling technologies.

Desired Skills & Experience

• 10+ Years of Technology leadership experience. While AI adoption is a business change, it is driven by transformational technology and we believe that understanding that technology and having a strong, fact based opinion on where it is going is important for success in this role. There are also strong technology underpinnings in the data and knowledge layer that requires a technical background to provide direction and vision for.
• Examples of cross company/functional leadership and change management
• Enthusiasm for AI but tempered by realism. We want to stay grounded on real value.
• Time in the trenches at B2B SaaS companies serving small businesses.
• We are a healthcare company and the trust of our customers is a privilege - background in regulated environments would be helpful and a security first mindset is required.

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 [e-mail].

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

$250,000—$315,000 USD