Description.
Industry: AI, HealthTech, Operations.
Work Arrangement: Fully remote (US time zones).
Job Type: Independent contractor, full-time.
Work Schedule: Flexible and asynchronous, 40–48 hours per week, with emphasis on agility.
Locations:
* Philippines.
* LATAM (Mexico, Colombia, Argentina, Brazil).
* Other remote regions with strong English communication and startup experience.
About Pearl Talent.
Pearl works with the top 1% of candidates worldwide and connects them with leading startups in the US and EU. Our clients have raised over $5B in aggregate and are backed by companies such as OpenAI, a16z, and Founders Fund. They are seeking strong, growth-driven candidates who can be consistently promoted over many years. Candidates hired through Pearl have been flown to the US and EU to work with clients and have even been promoted to roles equivalent to onshore positions in the US.
Why Work with Us?
At Pearl, we connect you with opportunities to work alongside visionary US and EU founders. Our focus is on placing you in roles where you can grow, be challenged, and build long-term careers.
About the Company.
Our client is an AI-powered healthcare advocacy startup focused on helping patients navigate the U.S. healthcare system with empathy and precision. They combine automation with human-centered support to help Medicare patients manage care plans, diagnoses, and medical billing while reducing administrative complexity. This fast-moving, high-impact company operates with a culture of ownership, humility, and execution.
Role Overview.
We are hiring an Executive Assistant / Admin Specialist (AI-driven operations partner) to serve as the operational backbone for the founding team. You will manage time, systems, and communication, anticipate needs, drive alignment across priorities, and enable the founders to focus on strategy, partnerships, and growth. This high-trust, high-autonomy role is ideal for someone who thrives in startup environments and is excited about the potential to grow into a Chief-of-Staff position.
Your Impact.
* Maximize founder leverage by managing time, tasks, and communication with precision.
* Build and maintain operational systems that enhance clarity and efficiency.
* Act as a communication hub, ensuring updates, deliverables, and follow-ups are completed.
* Drive accountability through structure, tools, and problem-solving.
* Improve operational workflows through automation and continuous optimization.
Core Responsibilities.
Founder Support and Communication – 35%.
* Maintain founder inboxes and calendars with the goal of inbox zero.
* Draft, proof, and send internal and external communications.
* Prepare meeting briefs and follow-ups to ensure founders are context-ready.
* Manage task lists and close 90% or more of delegated items within 48 hours.
Operational Systems and Workflow Management – 30%.
* Maintain dashboards and documentation in Asana, Notion, and internal tools.
* Create and update SOPs to improve consistency and efficiency.
* Build structure around recurring workflows through automation and process mapping.
* Monitor task completion and reduce recurring errors or missed deadlines.
Recruiting and Strategic Coordination – 20%.
* Coordinate hiring pipelines and outreach for US-based roles.
* Research, screen, and communicate with potential talent and vendors.
* Support partner development, scheduling, and coordination for business initiatives.
Documentation and Strategic Projects – 15%.
* Manage internal communications such as weekly team updates and investor notes.
* Research tools and AI automations to improve operational speed and accuracy.
* Identify issues early and propose solutions.
Performance Expectations.
* Inbox and calendar accuracy maintained at 100%.
* 90% of delegated tasks completed within 48 hours.
* Zero recurring workflow errors or missed deadlines.
* Two to three new SOPs created or improved monthly.
* Meeting briefs prepared ahead of all key discussions.
* Ability to anticipate 80% of potential issues before escalation.
Requirements.
Must-Have.
* 3 or more years of experience as an Executive Assistant, Admin Specialist, or Operations Partner.
* Strong written and verbal English communication skills.
* Proven ability to manage calendars, inboxes, and founder-level communication.
* Skilled in Notion, Asana, Google Workspace, Slack, and automation tools such as Zapier or AI assistants.
* High attention to detail, organization, and time management.
* Proactive mindset with strong ownership and discretion in handling confidential information.
* Experience working directly with CEOs, founders, or startup leadership.
* Bachelor’s degree preferred.
Nice-to-Have.
* Background in healthcare, startups, or project management.
* Experience building SOPs or internal systems.
* Exposure to AI tools for automation and productivity.
* Familiarity with analytics, reporting, or data-driven decision support.
Tools Proficiency.
Required:
* Notion.
* Asana.
* Google Workspace (Docs, Sheets, Drive, Calendar).
* Slack.
* Zapier.
Preferred:
* Airtable.
* ChatGPT or AI assistants.
* LinkedIn or CRM systems.
* Loom.
Benefits.
* Competitive salary based on experience and skills.
* Fully remote work.
* Career growth with a path to Chief-of-Staff within 2–3 years.
* Generous PTO according to company policy.
* HMO coverage after 3 months for full-time employees in the Philippines.
* Direct mentorship from international industry experts.
* Access to learning and development resources.
* Global networking opportunities.
Our Recruitment Process.
* Application.
* Screening.
* Skills assessment.
* Top-grading interview.
* Client interview.
* Job offer.
* Client onboarding.
Ready to Join Us?
If you are proactive, hyper-organized, and passionate about helping founders operate at peak performance, we welcome your application. Apply now and contribute to scaling an AI-driven healthcare startup reshaping patient advocacy.
