Our Leadership Team

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.

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.

Ryan Crapser brings with him over a decade of employee benefits administration experience. He began his career at Choice Strategies as the New England sales representative. After acquiring Choice Strategies, he would later go on to serve as the Director of Sales for Carrier & Exchange Partnerships at WageWorks, where he oversaw sales with national payroll providers, health plans, insurance carriers, national benefit brokerages, private exchanges, and benefit administration providers. Most recently Ryan served as Vice President, Strategic Partnerships at Businessolver.
 
Ryan oversees Clarity’s Strategic Partnerships. Through his leadership Clarity offers national payroll and HCM/HRIS providers, health plans, insurance carriers, exchanges, Benefit Administration solution providers, financial institutions, associations, Group Purchasing Organizations (GPOs) and Professional employer organization (PEOs) a unique and robust suite of consumer benefits, world-class service, hands-on sales, and operational support, and highly customized marketing support.
 
Ryan believes that every strategic partnership is unique and different from the other. His approach is to dive in and, at the ground level, learn a partner's business in terms of its culture, people, value proposition, strategy, key stakeholders, processes, and service delivery. He is passionate about the work that goes into two organizations developing and harmonizing processes, administration, training, marketing, sales, and service to ensure that our delivery of a joint solution is as frictionless as possible for internal and external stakeholders.
 
Ryan grew up in Massachusetts and attended Trinity College (CT). After college, he lived in Stamford, CT and New York City. Ryan and his wife now reside in Los Angeles, CA and remains avid Boston Sports team fan. Away from the office, Ryan enjoys traveling, hockey, golf, hiking, sailing, and boxing.

Eunice joins Clarity after being the Sr. Director, Integration Management Office at WageWorks, where she was responsible for deriving cross-functional strategic initiatives such as process improvements. In this capacity, Eunice positively impacted financial reporting, operational excellence, system consolidations and integrations to improve efficiencies and service delivery.

Before this position, Eunice was Sr. Director, Relationship Management for WageWorks. She guided a group of 40 Relationship Managers in all aspects of contract management, leadership development, and expanding client relationships. In this role, Eunice was responsible for overseeing $40MM in revenue and her team retained more than 95% of client revenue along with an 8.5/10 satisfaction rate. Before taking on this role and at WageWorks, Eunice was Manager, Relationship Management and oversaw 12 Relationship Management professionals' efforts handling $12MM in revenue. In this position, Eunice was also responsible for successfully integrating several portfolio purchases into the WageWorks service model.

Eunice began her career at WageWorks as a Sr. Relationship Manager responsible for the satisfaction and retention of enterprise and national accounts. Eunice achieved a satisfaction rating of 9/10 and 100% client retention while increasing client revenue by $3MM. Eunice began her Employer Services career at ProBusiness, where she was an Implementation Analyst/Project Manager responsible for the onboarding of their payroll application for enterprise clients.