Chief Human Resources Officer (CHRO) - AI-First Healthcare Technology Holding Company

Chief Human Resources Officer (CHRO)

Employment Type: Full-Time | Remote | Executive Leadership

About Ciullo, Inc.

Ciullo, Inc. is a fast-moving, AI-first holding company building and scaling a portfolio of high-impact businesses across healthcare technology, people operations, and digital innovation. We operate like a startup at every layer — fast decisions, bold bets, and a relentless focus on building the future. Our team is distributed, purpose-driven, and obsessed with using artificial intelligence to fundamentally transform how organizations operate.

Our core values — Resilience, Innovation, Passion, Ownership, Urgency, and Transparency — are not aspirational. They are operational.

The Role

The Chief Human Resources Officer is the most senior people leader in the company and a true strategic partner to the CEO and executive team. This is not a traditional HR role. We are looking for a transformational operator who has built people functions from the ground up in high-velocity startup environments, who leads with an AI-first mindset, and who can simultaneously hold strategy, culture, and execution across multiple business units.

You will own the full people agenda — talent strategy, organizational design, culture, compensation architecture, AI-powered HR operations, and executive team development — while moving at the speed of a startup scaling across multiple markets.

AI Fluency Requirement — Non-Negotiable

Ciullo, Inc. is an AI-first organization. Every member of our leadership and operations team is expected to actively use AI tools in their day-to-day work — not as a novelty, but as a core productivity multiplier. This role requires genuine curiosity about AI, comfort experimenting with tools like Claude, ChatGPT, and workflow automation platforms, and the judgment to know when AI helps and when it doesn’t. If AI makes you uncomfortable, this is not the right role.

What You Will Own

People Strategy & AI-First Operations

• Architect and execute a company-wide people strategy aligned to Ciullo’s multi-entity growth roadmap
• Deploy and expand AI-powered HR tools across recruiting, onboarding, performance management, and workforce analytics
• Build scalable, intelligent people processes that replace manual workflows with AI-assisted systems
• Lead organizational design across all portfolio companies
  
  

Talent Acquisition & Development

• Own recruiting strategy from executive hires to high-volume roles across all business units
• Build world-class onboarding and development programs that drive retention and time-to-productivity
• Create leadership pipelines and succession plans for every critical role across the portfolio
• Partner with business unit leaders on workforce plans and headcount models 6–12 months ahead
  
  

Culture & Employee Experience

• Define, protect, and evolve Ciullo’s culture across a distributed, multi-company structure

Interested in remote work opportunities in Human Resource? Discover Human Resource Remote Jobs featuring exclusive positions from top companies that offer flexible work arrangements.

• Design engagement strategies that drive belonging, accountability, and performance
• Lead DEI strategy with measurable outcomes — not performative programs
• Build a feedback culture powered by real-time data and AI-assisted sentiment tools
  
  

Executive Coaching & Leadership Development

• Coach and advise the CEO and senior leadership team on organizational effectiveness and team dynamics
• Build and facilitate leadership development programs for directors and above
• Directly mentor the SVP of HR — expanding their executive presence and preparing them to operate at the CHRO level
• Cascade leadership development throughout the entire people function
  
  

Compensation, Benefits & HR Infrastructure

• Design competitive, market-benchmarked compensation frameworks across all business units
• Oversee benefits strategy, vendor management, and total rewards philosophy
• Ensure HR compliance across all jurisdictions — employment law, labor regulations, and policy
• Partner with Finance on workforce budgeting, headcount planning, and people-cost optimization
  
  

Qualifications

Must Have

• 12+ years of progressive HR leadership experience with at least 5 years in a VP or C-suite people role
• Proven experience scaling people functions in startup or high-growth environments — you have built from 0 to 1 and from 1 to 100
• Demonstrated AI-first approach — you actively use AI tools in your work and have implemented AI-powered HR systems at scale
• Experience leading people strategy across multiple business units, departments, or portfolio companies simultaneously
• Exceptional change management skills — you thrive in ambiguity and lead others through it with confidence
• Track record of operating at both the strategic and operational level — you can think 3 years ahead and still roll up your sleeves
• Deep expertise in organizational design, compensation architecture, talent acquisition, and culture development

Browse our curated collection of remote jobs across all categories and industries, featuring positions from top companies worldwide.

• Strong executive presence and communication skills — you are a trusted advisor to CEOs and boards
  
  

Strong Differentiators

• CHRO or VP People experience at a venture-backed or PE-backed company
• Background across multiple industries or portfolio companies in a holding company structure
• Proficiency with ADP WFN and AI tools (Claude, ChatGPT, etc.)
• Experience building and managing remote-first or globally distributed teams
• MBA or advanced degree in Organizational Psychology, HR, or related field
  
  

Compensation

Compensation & Benefits

• Base Salary: $215,000 – $255,000
• Performance Bonus: Up to 35% of base — paid monthly and quarterly
  
  

Benefits Include

• Medical, dental, and vision benefits
• Unlimited PTO with a 10-day minimum encouraged
• 401(k) Plan with 3.5% Company Match
• Company-provided equipment
• Fully remote
  
  

Join Our Mission-Driven Team

At Ciullo, Inc., you’ll be part of a fast-growing organization that sits at the intersection of healthcare, technology, and compassion. Our team culture is collaborative, agile, and purpose-driven. Every role — from clinical operations and customer success to marketing, technology, and leadership — directly contributes to improving how healthcare organizations care for their patients.