Everyone can benefit

from someone to talk to

Sibly offers investors a mature product with current satisfied customers. Our skilled team brings over 150 years’ experience in healthcare and employee benefits and has the skills needed for commercial success.

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Company Type

Health Info Tech


$10 Million

Investment Type



Meet Sibly

What We Do

Sibly is a text-based AI-assisted coaching and benefit navigation service that provides immediate, 24/7 access to human coaches that help members take immediate action to improve their health while navigating them to the programs that meet their needs.


Sibly reduces the costs for chronic and co-morbid health conditions by guiding members to personalized employee benefit recommendations. Sibly amplifies the value of health and wellness programs and solves long standing problems for employers and health plans.


Our unique combination of human coaches, science- based interventions and AI drives reliable quality while reaching the profitability and scale of SaaS solutions.


The Opportunity

Sibly, a leading AI-assisted benefit navigation and health coaching platform, is seeking $10 million to accelerate growth and commercial adoption of its proprietary technology with payers, channel partners and employers.


With $4M closed, the round is led by Health Catalyst Capital with participation by BootstrapLabs.


At a time when AI is adding value across multiple dimensions of healthcare, Sibly provides a unique AI- enabled service that has already helped thousands of members improve their mental health and chronic conditions while saving millions of dollars for employers.


The Sibly Solution

AI – Assisted Benefit Navigation and Coaching Platform (AI-ANCP)


High-quality, AI-assisted, human conversations that motivate health behaviors and engage members in relevant benefits and services



Based on the needs of each member, we increase engagement in the benefits and services provided by the organization, lower costs and improve outcomes.


Sibly provides real-time, actionable data insight using AI and sentiment analysis. We deliver complex data insights into the needs, emotions and attitudes of a population.


A Mission-Driven Team

Bringing 150+ Years of Industry Experience

Paula Wilbourne PhD, Founder, CEO & Chief Product Officer

  • Deputy to the Associate Chief Consultant for Addictive Disorders of the Veterans’ Administration
  • Expanded quality and access for the largest integrated healthcare system in the US serving ~10 million veterans across ~1,400 sites
  • Mentored and advised by William R. Miller, the leading authority on Health Behavior Change and Motivational Interviewing
  • 20 years experience building and evaluating healthcare programs
  • Stanford postdoctoral fellow

Kevin McCarthy, President, COO & Director

  • Former President and CEO of Unum US, the largest disability insurance provider in the world
  • Senior positions of increasing responsibility across Unum since joining in 1976

CJ Mark, Chief Commercial Officer

  • Former CRO of UMR & Gallagher Benefits President
  • Former CCO of Vida Health. Grew their business from 24 clients to 500
  • 25+ yrs employee benefits experience including 15 years in Telehealth & Virtual Care
  • Led US market for Teladoc

Cindy Eaton PhD, VP of Coaching

  • Designed and implemented leading science-based treatment programs for patients with complex physical and mental health concerns
  • MINT trained trainer with over 20 years experience

Windy Molezzo, VP, Client Relations

  • Former Director Client Success, Doctor on Demand

  • 20+ yrs health care experience ranging from employee health & wellness and health plan/TPA/enterprise client management

Robert Arnetoli, CTO

  • Serial Founder/CTO and Senior Manager across leading organizations including Prosper, Western Union, Capital One and One Medical with domain expertise in scaling architecture, Big Data, AI, and Machine Learning
  • 20+ years building innovative and scalable AI technology solutions
Learn More About Sibly
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Hi. We're not around right now. But you can send us an email and we'll get back to you, asap.

Thanks, Ken

Ken Margolis | Managing Partner Castle Placement, LLC
1460 Broadway Street, Rte 400
New York, New York 10036
(212) 418-1188 | C: (516) 712-7784