EVP, Customer Success

EVP, Customer Success

Remote
Employment Type: Full-Time | Executive Leadership

About Ciullo, Inc.
Ciullo, Inc. is a Miami-based portfolio company founded in 2023 to unify and accelerate a growing family of healthcare services and technology businesses. Each company in the portfolio addresses a distinct and critical layer of the healthcare ecosystem, from remote care delivery and revenue cycle management to AI-powered platform infrastructure. Together, they operate as an integrated system designed to help providers deliver better care, capture more revenue, and reduce operational burden.

• Nsight Health 

• Focus Area: Remote Care Delivery

• What They Do: Fully managed RPM, CCM, PCM, CoCM, and BHI programs serving physician practices and health systems nationwide.
  

• Nsure

  • Focus Area: Revenue Intelligence

  • What They Do: Eligibility verification, insurance discovery, demographic completion, and propensity-to-pay analysis for provider organizations.
    

• Nvera

  • Focus Area: Revenue Cycle Management

  • What They Do: Full-service billing, credentialing, and revenue optimization delivered on a contingency basis for medical practices.
    

• Prvnt

  • Focus Area: AI Operating Platform

  • What They Do: HITRUST R2-certified orchestration engine powering omni-channel engagement, care workflows, documentation, and escalation across the portfolio

• Arryva

  • Focus Area: Short-Term Rental Operations

  • What They Do: Helps property owners and investors unlock the full earning potential of their real estate assets through professional short-term rental management.

Position Summary
Ciullo, Inc. is searching for a Senior Vice President of Customer Success who has done this before at speed and at scale. Not someone learning the craft, but someone who has already lived the hard chapters: the rapid growth that exposes weak retention infrastructure, the multi-client environments where every account feels like it needs white-glove attention, the moment you realize your team is reacting instead of leading, and the work it takes to turn that around.

This role launches with a primary focus on Nsight Health, our fastest-growing portfolio company, where the CS function needs to be elevated, systematized, and scaled to match the pace of the business. From there, it expands across the portfolio, building a unified CS capability that serves Nsure, Nvera, and Prvnt as each company continues to grow.

You will build the playbooks, the data infrastructure, the team culture, and the client relationships that turn our current book of business into an engine of retention, expansion, and referral. You will hire and develop CS leaders inside each entity, consolidate performance data across the portfolio, and bring a clear, honest view of client health to the executive team. And you will do all of this while staying close enough to the work that your team knows you have been in the room.

This is not a role for a polished presenter who delegates everything. It is a role for someone who is still willing to get on a call, untangle a difficult client situation, and teach their team exactly how it is done. This role reports directly to the Chief Revenue Officer.

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

Customer Success Strategy and Systems: Design and implement a scalable CS operating model across the Ciullo, Inc. portfolio, starting with Nsight Health and expanding to Nsure, Nvera, and Prvnt as the role matures. Build the playbooks, onboarding frameworks, QBR structures, escalation protocols, and expansion motion that shift the CS function from reactive account management to proactive client partnership. Establish a unified client health scoring system and own the metrics that matter: net revenue retention, gross revenue retention, time to value, expansion rate, churn rate, and customer satisfaction scores.

Multi-Entity Portfolio Management: Serve as the executive CS leader across all Ciullo, Inc. portfolio companies, adapting strategy and methodology to the distinct client types, sales cycles, and service models of each business. Understand the different economics of each entity, build bridges where shared clients or cross-sell opportunities exist, and consolidate performance reporting across the portfolio into a single executive view that gives leadership a clear, honest read on client health, risk, and growth potential at any given moment.

Team Leadership and Development: Recruit, develop, and lead a high-performing CS team across the portfolio including CS Managers, Account Managers, and Client Success Representatives embedded within each entity. Set clear performance standards, coach consistently, identify development gaps early, and build a culture where accountability and care for the client are equally non-negotiable. Act as a player-coach: present on key account calls, personally engaged in high-risk client situations, and consistently modeling the standard of client partnership you expect from the team.

Client Escalation Ownership: Personally own the highest-level client escalations across the portfolio, including those raised by sophisticated physicians who elevate their concerns to the executive team. Engage those clients directly, resolve situations with credibility and composure, and use each escalation as an opportunity to strengthen the relationship and sharpen the team. This is a defining responsibility of the role.

Client Retention and Expansion: Own net revenue retention across the portfolio as your primary performance metric. Build the motion that keeps clients, grows them, and turns them into advocates. Develop and execute a structured expansion playbook that identifies upsell and cross-sell opportunities within the existing book of business, and build executive-level relationships with key clients across the portfolio.

Data, Reporting, and Continuous Improvement: Build the data infrastructure that gives the CS team real-time visibility into client health across all portfolio companies, reducing reliance on manual reporting and reactive problem detection. Use AI tools and automation to scale CS operations including automated health scoring, proactive outreach triggers, and intelligent escalation routing. Present clear, narrative-driven CS performance reports to the CEO and executive team on a regular cadence.


The Impact You’ll Make

Retention Engine Builder: You will take a CS function that is growing fast and build the infrastructure, playbooks, and team culture that turns the existing book of business into a durable engine of retention, expansion, and referral across six companies.

Portfolio-Level CS Leader: You will be the executive CS voice across the entire Ciullo portfolio. When a client relationship is at risk, when a physician escalates, or when a cross-sell opportunity needs a senior sponsor, your name is the answer.

Team Architect: You will hire and develop the CS leaders inside each entity. The standard you set, the coaching you deliver, and the culture you build will determine what kind of CS organization Ciullo has for years to come.

Commercial Growth Driver: Net revenue retention is not just a metric here. It is how the portfolio compounds. Every point of NRR improvement you drive has a direct and measurable impact on the value of the business.


Qualifications

Required:

• 10 or more years of experience in Customer Success, Client Services, or Account Management with at least 4 years in a senior or executive CS leadership role

• Proven experience scaling a CS function inside a fast-growing company, ideally one that was doubling or tripling annually and where infrastructure had not kept pace with growth

• Demonstrated ability to manage CS across multiple client types, service models, or business lines simultaneously with the discipline to tailor approach while maintaining operational consistency

• Direct experience building CS systems from early-stage foundations including playbooks, health scoring models, QBR frameworks, onboarding programs, and expansion motions built for scale

• Strong financial and commercial acumen; you understand unit economics, you know what net revenue retention means at the business level, and you can speak to the executive team in those terms

• Experience working across or within a healthcare services or healthcare technology environment; you understand the complexity of healthcare buyer relationships and the stakes involved in client retention in this industry

• Track record of building and leading teams across remote environments with high accountability and consistent performance standards

• High AI fluency with active, working knowledge of AI tools in your daily professional workflow

• Strong analytical ability to build a health scoring model, diagnose a retention problem at the root cause level, and present a data-backed plan for fixing it

Preferred:

• Experience supporting a portfolio or multi-brand company where CS strategy had to be adapted across distinct business models under a shared parent organization

• Familiarity with remote care, RPM, CCM, or chronic care management programs and the unique dynamics of provider-facing client relationships in that space

• Experience with RCM, billing, or revenue intelligence products and the client relationships that come with contingency-based or performance-linked service agreements

• Hands-on experience building CS infrastructure inside a CRM platform such as HubSpot or Salesforce including pipeline management, health score automation, and reporting dashboards

• Background in a PE-backed or venture-backed high-growth environment where speed, precision, and accountability were organizational expectations rather than aspirations

• Experience building cross-sell and upsell motions within an existing book of business that contributed measurably to net revenue retention performance
  

Compensation & Benefits

• Competitive base pay: $170,000 – $190,000 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.