About Us

Self Bill Pro is revolutionizing benefits billing for the modern workplace. Founded in 2023 by a team of passionate benefits and technology professionals, we're driven to simplify complex processes and empower businesses to take control of their employee benefits spend. With the support of our investors, advisors, and team members, we're growing rapidly and poised to transform the way the benefits industry processes payments.

Mission & Vision

We love self-billing so much that we built a business around it. Self Bill Pro exists to empower employers and brokers through self-billing, turning what has traditionally been a complex and time-consuming process into an effortless one.

We want to transform employee benefits billing by providing automated solutions that prioritize accuracy, transparency, and compliance.

At Self Bill Pro, our mission is simple: to help businesses unlock the incredible benefits of self-billing, ensuring accuracy and compliance with every bill, without the hassle.

21

Connected HRIS Platforms

100%

Invoice Accuracy

Self Bill Pro finally made our benefits billing simple and easy.  With several hundred employees, carrier invoices were never correct and reconciling them took days.  Now, Self Bill Pro creates accurate invoices for us every month, with all the backup detail we need.

Karen Eads
Director, Human Resources

Senior Management

Mark Phillips

Senior Implementation Manager

Patrick Glennon

Chief Technology Officer

Andy Leach

Senior Account Manager

Matt Rollins

Director of Operations

Megan Blaylock

Operations Coordinator

Ann Kozlova

Lead Product Manager

Sophie Mondaca

Sales and Marketing Coordinator

David Erani

Lead Data Analyst

Sergey Volynets

Lead Software Engineer

Josh Winigrad

Founder, Chief Executive Officer

Rikki Cronk

Senior Implementation Manager

John Geschrey

Senior Account Manager

Jack Roudabush

Data Analyst

Mark Phillips

Senior Implementation Manager

Patrick Glennon

Chief Technology Officer

Andy Leach

Senior Account Manager

Matt Rollins

Director of Operations

Megan Blaylock

Operations Coordinator

Ann Kozlova

Lead Product Manager

Sophie Mondaca

Sales and Marketing Coordinator

David Erani

Lead Data Analyst

Sergey Volynets

Lead Software Engineer

Rikki Cronk

Senior Implementation Manager

John Geschrey

Senior Account Manager

Jack Roudabush

Data Analyst

Josh Winigrad

Founder, Chief Executive Officer

Our Experience in Self-Billing

Traditionally, benefits billing required employers to rely on insurance carriers to generate invoices—a process that often led to inaccuracies and delays, especially for large organizations with frequent employee changes. Employers needed a better way to take control of their billing.

In contrast, self-billing allows employers to calculate their own insurance premiums, ensuring invoices reflect up-to-date employee coverage details. However, creating accurate self-bills can be time-consuming and complex. That’s where Self Bill Pro started.

Self Bill Pro was born from a simple idea: self-billing doesn’t have to be hard. We began with a vision to eliminate manual billing errors. This vision evolved into a platform that integrates with leading HR systems, automates calculations, and delivers carrier-approved accuracy.

Operating from all across America, we combine cutting-edge technology with human expertise to deliver accurate, timely, and carrier-approved invoices. Every month, we personally review your billing data, ensuring that no discrepancies slip through. We’ve grown into a trusted partner for organizations seeking precision and peace of mind in their billing processes.

Board Members & Advisors

David Edwab

Board Member

Tom Kovatch

Board Member

Tim Theriault

Board Member

Jack Russi

Advisor

Join the Team

We’re a team of passionate innovators dedicated to solving real-world challenges in employee benefits billing. At Self Bill Pro, we believe in fostering a collaborative and inclusive work environment where great ideas thrive. If you’re ready to make an impact, we’d love to hear from you.