Director of AI Enablement & Advancement

Role Description

Spring Health is actively seeking a Director of AI Enablement & Advancement to join our People Team. Reporting directly to the Senior Director of Employee Experience, this person will own the strategy and execution of advancing AI fluency, rebuilding manual workflows across the organization, and support AI transformation efforts across the company. This is a full-time position that is fully remote-friendly, with occasional travel required for company-wide on-sites and team meetings.

What you’ll own:

• Company-wide AI Enablement:
  • Design and own a company-wide AI fluency progression framework that defines clear, role-anchored benchmarks for advanced AI usage across all business levels.
  • Build and deliver advanced learning experiences and workshops focused on agentic AI, automation design, and multi-step workflows.
  • Partner with functional leaders across the organization to identify role-specific AI use cases and implement targeted enablement programs to close operational skill gaps.
  • Establish and maintain scalable public knowledge infrastructure within internal communication platforms to make AI prompts, workflows, and use cases searchable and reusable.
  • Develop frameworks, toolkits, and standard operating procedures that empower internal teams to independently evaluate and rearchitect their own workflows.
• AI Operations and People Advancement:
  • Be a technical thought partner to our People Leadership Team, supporting core People Team workflows across Talent Acquisition, People Business Partners, Learning & Development, Total Rewards, and People Operations to eliminate manual effort and reduce operational latency.
  • Build systematic AI capabilities within critical functions across the org, establishing durable process standards and playbooks that embed AI into daily operations by default.
  • Transform traditional performance and development programs into continuous, AI-assisted systems that actively drive a day-to-day coaching culture.

What you’ll support:

• Audit high-volume, high-friction manual workflows across various business functions and lead end-to-end process redesign initiatives to make them fundamentally AI-native.
• Partner with executive leaders and People Business Partners to guide organizational design initiatives, evaluating and adjusting team structures to maximize the impact of AI-native workflows.

What success looks like:

• Redesign and deploy the company-wide performance and development framework within nine months, driving a measurable increase in continuous coaching touchpoints and match rate between managers and their direct reports.
• Establish and launch the company-wide AI fluency progression framework across all core departments within the first six months of hire.
• Audit and successfully redesign at least three high-volume manual corporate workflows into AI-native processes within the first year, demonstrating measurable reductions in processing time or operational friction.
• Support change efforts to create a more public infrastructure for knowledge and context sharing (in Slack, etc.).

Qualifications

• 8–12+ years of experience in enterprise change management, workforce transformation, organizational development, or digital enablement. Consulting, product, engineering or business operations experience strongly preferred.
• Proven track record of building scalability programs that advance employee technical depth from basic tool usage to advanced AI workflows, agents, and automations.
• Hands-on experience leading end-to-end process discovery, redesign, and change management for high-volume manual workflows.
• Familiarity with core People Team functions including talent acquisition, learning and development, and total rewards preferred.
• Strong functional understanding of generative AI, large language models, agentic workflows, and basic AI governance principles.
• Exceptional written and verbal communication skills, with a demonstrated ability to translate complex technical concepts clearly for non-technical audiences and executive leadership.
• Proven ability to influence and align cross-functional stakeholders effectively without direct formal authority.
• Demonstrated systems-thinking mindset with high comfort navigating ambiguous organizational environments.
• High emotional intelligence and experience guiding teams through technological change or workforce anxiety.
• Experience operating successfully as a senior individual contributor driving enterprise-wide strategic programs.

Nice to have:

• Prior experience working within a fast-growth technology, healthcare, or employee benefits company.
• Experience designing scaled organizational knowledge management systems on modern internal collaboration platforms.

Requirements

• The target base salary range for this position is $180,000-225,000 and is part of a competitive total rewards package including stock options and benefits. Individual pay may vary from the target range and is determined by a number of factors including experience, location, internal pay equity, and other relevant business considerations.

Benefits

• Health, Dental, Vision benefits start on your first day at Spring. You and your dependents also receive access to One Medical accounts. HSA and FSA plans are also available, with Spring contributing up to $1K for HSAs, depending on your plan type.
• Employer sponsored 401(k) match of up to 2% for retirement planning.
• A yearly allotment of no cost visits to the Spring Health network of therapists, coaches, and medication management providers for you and your dependents.
• We offer competitive paid time off policies including vacation, sick leave and company holidays.
• At 6 months tenure with Spring, we offer parental leave of 18 weeks for birthing parents and 16 weeks for non-birthing parents.
• Access to Noom, a weight management program—based in psychology, that’s tailored to your unique needs and goals.
• Access to fertility care support through Carrot, in addition to $4,000 reimbursement for related fertility expenses.
• Access to Wellhub, which connects employees to the best options for fitness, mindfulness, nutrition, and sleep in one subscription.
• Access to BrightHorizons, which provides sponsored child care, back-up care, and elder care.
• Up to $1,000 Professional Development Reimbursement a year.
• $200 per year donation matching to support your favorite causes.