Chief Human Resources Officer

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About the Job

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
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
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.

Location: United States (Remote)