Remote opportunity at
Pearl TalentRemote Chief of Staff
Pearl Talent is assisting a private equity-backed health technology firm that serves Medicare Advantage plans and risk-bearing providers in hiring a remote Chief of Staff. This…
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About This Role
Pearl Talent is assisting a private equity-backed health technology firm that serves Medicare Advantage plans and risk-bearing providers in hiring a remote Chief of Staff. This full-time position operates with US Eastern business hours overlap, including early mornings and occasional weekend availability. The employer is scaling rapidly, expanding from approximately 40 to 160 employees by the end of the first quarter, with operations spanning the United States and Puerto Rico.…
Job Description
Pearl Talent is assisting a private equity-backed health technology firm that serves Medicare Advantage plans and risk-bearing providers in hiring a remote Chief of Staff. This full-time position operates with US Eastern business hours overlap, including early mornings and occasional weekend availability. The employer is scaling rapidly, expanding from approximately 40 to 160 employees by the end of the first quarter, with operations spanning the United States and Puerto Rico. Because many existing workflows currently rely on email, text messages, and phone calls, this professional will build foundational operating structures from scratch.
Initially, the role comprises about 80 percent executive administration and 20 percent operations, focusing on calendar and inbox management for the Chief Operating Officer, board logistics, billing, compliance for a Puerto Rico-based client, and monthly state regulatory filings. As trust develops, responsibilities transition into a balanced strategic operations partnership. Candidates should possess strong administrative and systems-building capabilities to help streamline company growth and improve patient access to specialized healthcare across the United States.
Responsibilities
- Manage the COO schedule across internal operations, board meetings, and client travel
- Triage the Outlook inbox and draft messages on behalf of the COO
- Organize board meeting logistics, member communications, and follow-up activities
- Maintain a follow-up tracking system for open action items across the leadership team
- Act as the primary daily operational contact for a Puerto Rico Medicare Advantage health plan client
- Reconcile invoices, handle billing, and complete client compliance attestations
- Schedule meetings with client administrative teams in Spanish and assist the COO during visits with coordination and translation
- Submit recurring monthly state-by-state regulatory forms and track multiple state compliance deadlines
- Author standard operating procedures for recurring regulatory processes and coordinate document collection
- Implement project and task tracking systems using tools like Smartsheet
- Create operational playbooks, document processes, and identify bottlenecks to recommend automations
- Coordinate onboarding logistics for new hires during the hiring expansion
Requirements
- Minimum of 4 years of professional experience, including at least 2 years as a Chief of Staff, C-suite Executive Assistant, or Executive Operations Manager
- Background working at a venture capital- or private equity-backed startup or scale-up with 30 to 200 employees
- Hands-on proficiency with Microsoft Outlook for calendar and inbox management
- Experience using Microsoft Excel for reporting, tracking, pivot tables, and reconciliations
- Practical experience building and maintaining trackers in Smartsheet, Asana, ClickUp, Notion, or comparable project management software
- Demonstrated experience building, documenting, and maintaining at least one standard operating procedure, tracking system, or workflow from scratch
- Client-facing coordination background handling scheduling, billing, or invoice reconciliation with external stakeholders
- Native or C1+ fluency in both Spanish and English based on the CEFR scale
Qualifications
- Background in healthcare, Medicare Advantage, health plans, or other regulated industries such as fintech or insurtech
- Familiarity with recurring regulatory or compliance filings and deadline tracking
- Daily use of Todoist or artificial intelligence productivity tools
- Experience tracking account profit and loss statements or building financial data visualizations
- Consulting or business school background combined with hands-on execution experience
Core Skills
Benefits
- Competitive salary determined by experience and skills
- Fully remote work arrangement with the ability to work from anywhere
- Team incentives recognizing 100 percent CRM hygiene and on-time reporting
- Generous paid time off in accordance with company policy
- Health coverage providing HMO protection after three months for full-time employees based in the Philippines
- Direct mentorship from international industry experts
- Ongoing access to learning and development resources for professional growth
- Opportunities to connect with professionals worldwide through global networking
Frequently Asked Questions
Answers are based only on the employer’s listing; where it doesn’t say, neither do we.
Is this position fully remote?
Yes, the posting specifies that the role is fully remote and allows work from anywhere, operating with US Eastern business hours overlap.
What is the salary for this role?
The specific salary is not stated in the posting, though compensation is noted as competitive and based on experience and skills.
What language skills are required?
Candidates must have native or C1+ fluency in both Spanish and English according to the CEFR scale.
What does the recruitment process involve?
The recruitment process includes application screening, a skills assessment, a Topgrading interview, a client interview, a job offer, and client onboarding.
Sample Interview Questions
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