About Ciullo, Inc. Ciullo Inc. is a Boca Raton-based privately held holding company building enduring businesses in healthcare, technology, and wellness. Twice recognized on the Inc. 500 for building separate high-growth companies from the ground up, we don't just identify opportunity. We apply operational rigor and institutional capital to turn it into something lasting. Our portfolio spans six companies across four sectors, with a collective team of 500+ and an expanding footprint across some of the fastest-growing verticals in the country. Our healthcare and technology brands include Nsight Health, a healthcare SaaS platform managing 350+ clinics in Remote Patient Monitoring, Chronic Care Management, and complex chronic care programs; Nsure, our revenue cycle and verification division; Nvera, our dedicated Revenue Cycle Management division; and PRVNT (prvnt.ai), our AI-powered healthcare technology platform. Beyond healthcare, our portfolio includes Arryva, a full-service short-term rental operations company, and The Sweat Room, Boca Raton's premier hot pilates and sculpt studio. Our core values of Resilience, Innovation, Passion, Ownership, Urgency, and Transparency are not aspirational. They are operational. Position Summary Ciullo, Inc. is looking for a Director of Revenue Operations who wants to own something real. This is the commercial data backbone of a multi-company portfolio, and the person in this seat will have direct access to senior leadership, full ownership of the systems and numbers that drive decisions, and the autonomy to build something that actually scales. This is a fully remote individual contributor role. You do not carry a quota, you do not manage a team, and you do not travel. What you do is build the infrastructure, maintain the integrity of the data, and show up prepared to every leadership touchpoint with clean, accurate, and actionable information across Nsight Health, Nsure, PRVNT, Nvera, and Arryva. If you are energized by the challenge of bringing order to a fast-moving, multi-entity commercial operation and you want your work to matter at the highest level of the organization, this role was built for you. 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.
Key Responsibilities
HubSpot CRM Ownership: Own and govern the full HubSpot CRM ecosystem across all portfolio companies, including pipeline configuration, workflow automation, and reporting infrastructure. Maintain clean, auditable data across all commercial roles and drive adoption and proper utilization across SDR, AE, and Customer Success functions. Manage integrations with supporting platforms including Apollo and LinkedIn Sales Navigator.
Revenue Reporting and Forecasting:Own all revenue forecasting across the Ciullo, Inc. portfolio, delivering accurate monthly, quarterly, and annual projections to senior leadership. Build and maintain pipeline coverage models using historical data and cross-entity commercial trends. Produce standardized reporting across all brands with consistent methodologies and definitions so leadership always has one version of the truth. Participate in weekly huddles across commercial, finance, and operations functions, presenting data-driven updates on pipeline health, forecast accuracy, and performance trends across the portfolio.
Quota Architecture and Compensation Administration: Design bottoms-up quota models, territory frameworks, and sales capacity plans aligned to growth targets. Design, calculate, and administer all variable compensation plans across the full commercial organization including SDRs, Account Executives, Customer Success Managers, and Customer Success Liaisons. Model compensation scenarios to support new hire planning, quota changes, and organizational restructuring. Maintain clean, auditable compensation records and deliver timely payout calculations to Finance.
Cross-Functional Alignment: Act as the revenue operations point of contact for Finance, Clinical, Compliance, and Implementation teams on matters related to commercial data, reporting, and process governance. Support pricing analysis, deal economics, and P&L inputs in partnership with senior leadership. Identify and flag commercial process gaps across the organization and recommend solutions that improve efficiency at scale.
The Impact You’ll Make
Commercial Backbone: You will be the single source of truth for revenue data across a six-company portfolio. When senior leadership makes a growth decision, they will make it with your numbers. That is a meaningful seat at the table.
Systems Builder: You will take a multi-entity HubSpot environment and turn it into a clean, scalable, and trusted operating infrastructure. The commercial organization will run better because of what you build.
Compensation Architect: Every SDR, AE, and Customer Success Manager across the portfolio will be paid on plans you designed. When the incentives are right, the behaviors follow. That is downstream impact on revenue growth.
Operational Force Multiplier: By identifying process gaps, building coverage models, and delivering clean forecasting, you will give leaders across every brand the visibility they need to move faster and with more confidence.
QualificationsRequired:
5 or more years of progressive experience in Revenue Operations, Sales Operations, or a closely related commercial function
Expert-level proficiency with HubSpot CRM including pipeline architecture, workflow automation, and executive reporting
Demonstrated ability to build revenue forecasting models, quota architectures, and territory frameworks in a high-growth environment
Proven experience designing and administering variable compensation plans across multi-role sales organizations
Strong analytical skills with the ability to translate complex commercial data into clean, leadership-ready reporting
Industry experience relevant to the portfolio, particularly in B2B healthcare services, health technology, or clinical operations environments
Preferred:
Experience supporting multiple operating companies or portfolio entities under a parent organization
Familiarity with RPM, CCM programs, value-based care models, or healthcare payer and provider ecosystems
Proficiency with BI and analytics platforms such as Domo, Tableau, or equivalent
Active, practical use of AI tools to accelerate reporting, analysis, and operational workflows
Compensation & Benefits
Competitive base pay: $150,000 – $160,000 annually.
Additional Compensation:
Performance-Based Bonus: Eligible for an annual bonus based on company and individual performance.
Benefits Include:
Unlimited PTO
Medical, Dental, Vision, and supplemental insurance options
401(k) Plan with 3.5% Company Match
Company-provided equipment
Join Our Mission-Driven Team
At Ciullo Inc., you won't be a cog in a corporate machine. You'll be a builder inside a portfolio of high-growth companies that started as ideas and became Inc. 500 honorees. We operate with the speed of a startup and the discipline of an institution, and we expect the same from everyone on our team. We are looking for people who are wired to build, not maintain. Operators who see a gap and close it, who take ownership without being asked, and who are energized by the challenge of doing something that has not been done before.
