Our Leadership Team
For over 30 years, our leadership team has provided best-in-class services for our benefit brokers, employers, and consumers. Our process has always been to provide meaningful solutions for today’s challenges while creating opportunities for the future.
As Founder and CEO Bill oversees every aspect of the business, his passion is sales, marketing and vision. Bill’s experience in the industry spans 30 years. Bill was a partner at Electronic Accounting Systems a midsize payroll service that he sold to ADP in 1991. Bill founded Clarity Benefit Solutions (formerly BeneFlex) in 1992, over the next two decades he founded and successfully sold several companies including Total Pay, and Paylocity of N.J. Bill is a Trustee for First Star Academy and an active alumni of St. Peters University where he received a BS in accounting.
Howard is an accomplished Human Capital Management industry professional and leader with more than 30 years of experience. He has been a member of the Clarity team since 2002. Howard oversees all strategies related to operations and service delivery. Howard has a passion for innovation and encourages teams to continually pioneer new practices, resulting in consistent, high-quality experiences for brokers, employers, and participants.
Over his career, from small businesses to national accounts, Howard has worked with teams to deliver superior, technology-based services. Prior to joining Clarity, Howard was the co-founder and Vice President of Paylocity of New Jersey where he was also responsible for all operation and service outcomes. Beginning in 1987 and through 2002 Howard served as President or Managing Partner of several privately held payroll companies and was responsible for all aspects of each enterprise. Each of these firms were ultimately acquired. Howard began his career as a salesperson at Electronic Accounting Systems where he became the top selling associate and rose to the position of Sales Manager. Howard is an alumnus of American University. Away from the office, Howard can usually be found spending time supporting the interests of his three boys.
Linda is the Vice President of Consumer Benefit Implementation and Renewal at Clarity Benefit Solutions. Linda is responsible for providing leadership, strategic direction and guidance to the Implementation and Renewal teams with a focus on successful client experiences and superior client service.
Linda is a seasoned consumer benefit administration professional with nearly 30 years in the industry. Over the course of her career, she has focused on full benefits outsourcing, consumer benefits and COBRA administration. Linda has successfully led highly effective national teams supporting the enterprise, strategic partner and small business market segments. Previously, Linda served as Director of Implementations for WageWorks, Inc. where she had the opportunity to oversee thousands of implementations each year.
Linda holds a Bachelor of Science in Education from Bridgewater State College. When away from the office, Linda enjoys spending time with her husband and daughter. Linda volunteers at her daughter's school and to support the International FOP Association's race for a cure.
Jill Schwartz is an accomplished and trusted business leader with over 20 years of experience partnering with internal and external clients in corporate, outsourcing and consulting environments.
As the Vice Present of Client Services, Jill leads Clarity’s Service Teams with an eye towards engagement and excellence. She began her career in Corporate Human Resources and later transitioned to work in Benefits Outsourcing and Consulting. Jill was part of the team launching BNY Mellon’s HSA administration business and later led Account Management for the Eastern Region at BenefitWallet, Conduent HR Services.
Jill holds a degree in Human Development from Cornell University and an MBA from New York University.
Whether it be for internal or external clients, Jill’s approach to service is that organizations succeed through people and people do their best work when they are informed, empowered and appreciated. Jill’s view on service extends to her personal life where she focuses on family, friends and community service.
Linda helps develop and implement programs and projects that support the company’s vision, as well as, short and long-term goals. She has been a vital member of the team since 1999. Linda’s experience in the payroll and benefits industry spans more than 20 years. Linda’s strong technical knowledge and team focused approach helps to drive our client centric company culture.
Prior to Clarity Benefit Solutions, Linda had success working in and managing teams in the payroll industry, on Wall Street, and in the public sector. Outside of the office, Linda enjoys DIY work at home and spending time with her two children.
Jennifer Tomaselli has over 20 years of experience in the payroll, HR and benefit industry with a primary focus on technology for the last 12 years. Jennifer has extensive experience supporting and managing enterprise corporation's complex HRIS systems as well as managing client service for benefit administration platforms. Jennifer has demonstrated success in overseeing all phases of system implementation as well as ongoing customer service.
As Vice President of Benefit Technology, Jennifer is responsible for managing the COBRA and Ben Admin teams at Clarity. This includes oversight of all functions as they relate to the implementation and servicing of Clarity's clients. Jennifer and her team of dedicated operational analysts help facilitate new business and nurture Clarity’s important client relationships.
Prior to joining Clarity, Jennifer lead the Benefit Technology practice at Providence Technology Solutions, helping the start-up drive new benefit platform business while managing a team of 20 analysts. Jennifer also has managed the HRIS systems for The Triumph Group, Universal Health Services and The Devereux Foundation.
Jennifer currently lives in the suburbs of Philadelphia and is an alumni of Gettysburg College. Jennifer loves to travel to unique destinations whenever possible and has two teenage boys who keep her busy outside of work.
Bill Sowders is an industry veteran with nearly three decades of experience in the employee benefits space. He has a proven track record of growing high-caliber teams, contributing to bottom-line revenue and forging strong relationships with key industry brokers and customers.
At Clarity, Bill leads a world-class sales team responsible for shaping and growing Clarity’s sales initiatives to achieve the vision of the company, create and strengthen key partnerships, and grow overall company revenue.
Bill previously served in senior roles at WageWorks, including as Vice President of Mid-Market Sales where he managed a large sales team, and provided strategy and direction as a member of the Sales Leadership Team.
Bill currently lives in Atlanta and is an alumni of Georgia State University. Outside of the office, Bill enjoys time with his family at home and at the beach.
Krista Woolley is an accomplished marketing executive with over 20 years of experience in B2B/B2C marketing, marketing automation, content strategy, public relations, customer lifecycle communications, event management and business relationship management.
Through strategic marketing efforts, Krista is focused on helping grow Clarity’s marketshare, drive thought leadership, enhance our online reputation and brand equity and grow the company’s overall revenue.
Prior to joining Clarity, Krista lead the marketing efforts at WageWorks, helping to increase the company’s market share and driving overall revenue growth. Krista has also lead marketing efforts for FedEx Office, BNSF Railway and several other companies in the technology, transportation, retail and oil/gas industries.
Krista currently lives in Texas and is an alumni of the University of North Texas. Outside of the office Krista enjoys running and riding bikes, trying out new recipes and vacationing in Wisconsin.