About Alaffia & Our Mission

Every year, U.S. health plans lose billions to improper payments and administrative waste. That wasted spending ultimately trickles down across the healthcare ecosystem, driving up costs for plans, providers, and patients alike. We’re here to change that paradigm.

Alaffia is a new kind of claims operations partner for health plans. Using expert clinicians and transparent AI, we deliver deeper insights, smarter automation, and consistently better outcomes across the entire lifecycle of claims. With Alaffia, health plans can cut wasted spending more effectively than ever — and provide their members the most affordable care.

We’re a high-growth, venture-backed Series B healthtech startup based in NYC and are actively scaling our company. Join us in helping to build a healthcare system that works better for everyone.

About The Role

We’re seeking an Executive Assistant to our Cofounders, CEO TJ Ademiluyi and COO Adun Akanni, who will serve as a strategic partner and operational backbone, ensuring seamless execution of priorities in a fast-paced, high-growth environment.

The ideal candidate is proactive, resourceful, and energized by ambiguity. You’ll be the person who anticipates needs before they’re articulated, solves problems independently, and keeps complex operations running smoothly behind the scenes. This role offers exceptional exposure to executive decision-making, investor relations, and company building at a critical inflection point.

As Alaffia scales significantly over the next 1-2 years, this role will grow in scope and responsibility, with opportunities to take on strategic projects, build processes, and expand into broader functions.

Your Responsibilities

Calendar & Schedule Management

• We’re seeking an Executive Assistant to our Cofounders, CEO TJ Ademiluyi and COO Adun Akanni, who will serve as a strategic partner and operational backbone, ensuring seamless execution of priorities in a fast-paced, high-growth environment.
• The ideal candidate is proactive, resourceful, and energized by ambiguity. You’ll be the person who anticipates needs before they’re articulated, solves problems independently, and keeps complex operations running smoothly behind the scenes. This role offers exceptional exposure to executive decision-making, investor relations, and company building at a critical inflection point.
  
  

Travel & Logistics Coordination

• Arrange all domestic and international travel for both cofounders including flights, accommodations, ground transportation, and detailed itineraries
• At times, coordinate travel logistics outside standard business hours, including weekend trips, investor meetings, conferences, and customer visits
• Anticipate travel needs (visas, health requirements, meeting materials) and handle proactively
• Manage expense reporting and reconciliation for all cofounder travel and business expenses
  
  

Meeting & Event Support

• Coordinate executive team meetings, board meetings, all-hands, and investor updates
• Support after-hours events that may include networking receptions, investor meetings, and team gatherings
• Serve as on-site support for key meetings, ensuring seamless execution
  
  

Communication & Stakeholder Management

• Serve as first point of contact and gatekeeper for both cofounders, managing inbound requests and prioritizing appropriately
• Draft and edit correspondence including emails, memos, and presentations on behalf of the cofounders
• Maintain relationships with key stakeholders both internally and externally
• Handle sensitive and confidential information with absolute discretion and professionalism
  
  

Strategic & Operational Support

• Own special projects and ad-hoc initiatives as assigned by either cofounder
• Maintain systems for tracking cofounder commitments, action items, and follow-ups across all meetings
• Partner with cross-functional teams (Finance, People Ops, Legal, etc.) to support cofounder-driven initiatives
• Identify operational inefficiencies and proactively implement solutions to improve executive effectiveness
• Handle personal tasks as needed to free up cofounder time for strategic priorities
  
  

What We're Looking For

Required Experience & Qualifications

• 5-7 years of professional experience including at least 2-3 years supporting C-level executives (CEO, COO, President, Managing Partner, or equivalent)
• Experience at a startup, venture-backed company, or high-growth business strongly preferred (seed through late stage)
• Proven ability to manage complex, overlapping calendars, coordinate travel, and handle competing priorities in fast-paced environments
• New York City-based and able to work on-site 5 days/week in our SoHo office with flexibility around the cofounders’ schedules
  
  

Core Competencies

• Proactive problem-solver: You anticipate needs, identify issues before they escalate, and solve problems independently without constant direction
• Exceptional organizational skills: You juggle multiple priorities seamlessly, nothing falls through the cracks, and you thrive in organized chaos
• Discretion and judgment: You handle highly confidential information daily and make sound decisions about priorities, access, and communication
• Adaptable and resilient: Startup schedules are unpredictable, you're energized (not frustrated) by last-minute changes and shifting priorities
• Tech-savvy: Proficient in Google Workspace (Calendar, Gmail, Docs, Sheets), Slack, Zoom, scheduling tools (Calendly, etc.), and quick to learn new platforms
  
  

Work Style & Attributes

• High EQ and professionalism: You interact seamlessly with everyone from investors and board members to early employees and vendors
• Low-ego, high-agency: You're comfortable doing both strategic and administrative work—no task is beneath you if it helps the CEO or company succeed
• Detail-obsessed: You catch errors others miss, triple-check logistics, and have a reputation for flawless execution
• Availability-focused: You understand that supporting a startup CEO requires flexibility beyond traditional 9-5 hours, including occasional evening/weekend availability for urgent matters, travel coordination, or events
• Growth-minded: You're excited about growing your career as the company scales and want to take on increasing responsibility over time
  
  

Preferred Qualifications

• Healthcare, healthtech, or regulated industry experience
• Experience supporting executives through fundraising, M&A, or other high-stakes initiatives
• Project management or operations experience
• Interest in AI, technology, or healthcare
  
  

Our Culture

Alaffia was born out of our founders’ personal connection to the inefficiency of the U.S. healthcare system. We are deeply mission-driven, with an abiding belief that technology can help create a better future for everyone, and we’re looking for others who share our passion for change to join the team.

What Else Do You Get Working With Us?

• Competitive Compensation
• Medical, Dental, and Vision benefits
• Flexible, paid vacation policy
• Work in a flat organizational structure with direct access to Leadership