Director, Revenue Operations

Nsight Health• US,

8h•$150,000 - $160,000•Remote

About The Position

We are seeking a Director of Revenue Operations who builds, not just manages. This is a hands-on execution role for someone who takes personal pride in being the person leadership counts on to get the details right, move fast without sacrificing accuracy, and construct the commercial infrastructure that makes a multi-brand revenue organization run. Reporting to the Chief Revenue Officer, you will own the full revenue operations function across the Ciullo, Inc. portfolio, including Nsight Health, Nsure, PRVNT, Nvera, and Arryva. You are a master of HubSpot and backend reporting who turns raw commercial data into clean, decision-ready intelligence. You manage the infrastructure that powers forecasting, pipeline visibility, and compensation across every brand, and you come to leadership huddles prepared to walk through live, accurate reporting and adjust the analysis in real time as the business moves. If you have spent your career building things from scratch, running clean systems in complex multi-entity environments, and showing up to every leadership conversation with the data already done, 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.

Requirements

5 or more years of progressive experience in Revenue Operations, Sales Operations, or a closely related commercial function.
Expert-level mastery of HubSpot CRM, including pipeline architecture, workflow automation, custom reporting, and backend system management; candidates who have configured and built HubSpot from the ground up are strongly preferred.
Demonstrated ability to build and maintain revenue forecasting models, quota architectures, and territory frameworks in a fast-paced, high-growth environment.
Proven experience 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 and present it with confidence in a live setting.
Comfort operating across multiple brands and functions at speed, supporting both sales and customer success without losing accuracy.

Nice To Haves

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.
Practical use of AI tools to accelerate reporting, analysis, and operational workflows.
Familiarity with short-term rental management, hospitality technology, or property management operations.

Responsibilities

Own and build out the full HubSpot CRM ecosystem across all portfolio brands, including pipeline architecture, workflow automation, custom properties, and reporting infrastructure.
Build and maintain backend reporting and dashboards that give leadership real-time, full-funnel visibility into commercial performance across every entity.
Maintain clean, auditable, and accurate data at all times, holding every commercial function to a high standard of CRM hygiene and discipline.
Drive adoption and proper utilization across SDR, AE, and Customer Success teams, and manage integrations with supporting platforms including Apollo and LinkedIn Sales Navigator.
Build and manage revenue forecasting across the portfolio, delivering accurate monthly, quarterly, and annual projections built on clean data and sound methodology.
Construct and maintain pipeline coverage models using historical trends and cross-entity commercial data to support predictable, scalable growth.
Participate in weekly leadership and team huddles with live, active reporting, presenting pipeline health, forecast accuracy, and performance trends and adjusting analysis in real time as questions arise.
Produce standardized reporting across all brands using consistent definitions and methodologies so leadership always works from one version of the truth.
Build and maintain quota models, territory frameworks, and sales capacity plans in line with growth targets set by revenue leadership.
Calculate and administer 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 adjustments across all brands.
Maintain clean, auditable compensation records and deliver timely, accurate payout calculations to Finance.
Provide hands-on operational support across both sales and customer success functions, stepping in wherever the business needs reporting, analysis, or process help.
Serve as the revenue operations point of contact for Finance, Clinical, Compliance, and Implementation teams on matters related to commercial data, reporting, and process execution.
Support pricing analysis, deal economics, and P&L inputs in partnership with revenue leadership.
Identify and flag process gaps across the commercial organization and implement solutions that improve efficiency and scale in a fast-moving, multi-brand environment.