Sales VP

Want to be a bswifter?  

At bswift we’ve been transforming benefits administration since 1996, making it simpler, smarter, and more human. Our state-of-the-art, cloud-based technology and services empower employees to understand, manage, and love their benefits. From downtown Chicago, and remotely across the country, we serve thousands of companies and millions of people nationwide, reducing administrative burdens and freeing HR teams to focus on creating thriving, people-first workplaces.  

  We’re looking for motivated and goal-driven individuals who share our passion for delivering excellence and creating solutions that make a difference. The reward is a fun, flexible and creative environment with ample opportunity for professional and personal growth. If you love the bswift values of pursue excellence, embrace accountability, deliver superior service, and be a great place to work, we want to hear from you!  

ABOUT US bswift is a leading benefits administration company that specializes in providing tailored solutions for our clients. Our mission is to simplify the complex world of employee benefits and deliver exceptional service to our clients. We are looking for a talented and experienced individual to join our team as a Sales VP.

WHAT YOU’LL DO The Sales VP is responsible for driving growth in bswift’s direct business by selling our technology and services to large and mid‐market employers. This role owns the full sales cycle—from proactive prospecting through close—including RFP responses, pricing strategy, external meetings, and contract negotiation in partnership with internal legal teams. Successful candidates are collaborative, self‐motivated, and skilled at building long‐term, win‐win client relationships.

WHAT YOU WILL BE RESPONSIBLE FOR (Essential Functions) Reasonable accommodations may be made to enable individuals with disabilities to perform these essential functions.

Represent bswift’s technology and benefits administration services to prospective large and mid‐market employers Cultivate strong relationships with consultants, brokers, enrollment firms, and other external partners Develop prospect sales strategies and lead responses to RFPs Lead internal preparation for external sales efforts and all stages of prospect meetings Develop and execute regional sales and growth strategies Proactively prospect in assigned markets and build a strong local presence through market engagement Manage complex negotiations, positioning products, pricing, and expanded portfolios to maximize revenue Identify opportunities to partner with clients across bswift’s full product line Organize and deliver compelling presentations to internal and external stakeholders Negotiate contracts and letters of intent in collaboration with internal legal counsel

WHAT YOU NEED TO SUCCEED (Required Education and Experience)

10+ years of experience in a sales role Proven success selling benefits administration or insurance products to mid‐ and large‐market employers Experience managing complex sales processes involving senior‐level benefits, finance, IT, procurement, and consulting stakeholders Strong public speaking and presentation skills Bachelor’s degree or equivalent experience

NICE TO HAVE (Preferred Education and Experience)

Experience selling SaaS solutions in the HR and benefits space Established relationships with employee benefits consultants, brokers, or third‐party administrators

Why Join bswift?

At bswift, we empower our employees to make a meaningful impact, innovate, and grow. Joining our team means stepping into a collaborative and dynamic environment that values creativity, initiative, and a passion for client success. We are dedicated to fostering an inclusive workplace that celebrates diversity and values each team member’s unique contributions.

Benefits of Working at bswift:

Comprehensive Health Benefits : Access to health, dental, and vision plans to support your wellness and that of your family.

Competitive Compensation : A compensation package that recognizes your skills, experience, and contributions, including performance-based incentives for most roles.

Remote first, Office friendly environment!  No time to commute?  No problem!

Retirement Savings Plans : Options to help you plan for a secure financial future with employer-sponsored retirement savings programs.

Professional Development : Opportunities for career growth, including training and access to resources to support your career progression.

Supportive Culture : A work environment that encourages collaboration, open communication, and creative problem-solving, where your voice and ideas are valued.

Employee Wellbeing Initiatives : Programs focused on mental health, financial planning, and wellness resources to help you thrive inside and outside of work.

Make an Impact : At bswift, your work directly contributes to transforming how organizations approach benefits administration and client engagement. Join us to be part of an organization that is making a meaningful difference in the lives of our clients and their employees.

Specific benefit offerings vary by position and may be subject to change.

Standard working hours are 8am-5pm Central Time, unless otherwise stated in the Job Description. 

In the spirit of pay transparency, we are excited to share the base salary range for this position is $150,000-175,000, exclusive of fringe benefits or potential bonuses.  If you are hired at bswift, your final base salary compensation will be determined based on factors such as geographic location, skills, education, and/or experience. In addition to those factors – we believe in the importance of pay equity and consider internal equity of our current team members as a part of any final offer. Please keep in mind that the range mentioned above is the full base salary range for the role. Hiring at the maximum of the range would not be typical in order to allow for future & continued salary growth. We also offer a generous compensation and benefits package!

At bswift, our mission is clear: Become the preeminent benefits administrator through exceptional people, innovative technology, and delighted customers. And our values are at the heart of everything we do to accomplish that mission. We  Pursue Excellence, Embrace Accountability, Deliver Superior Service, and strive to Be A Great Place To Work . We take pride in having an engaged, collaborative team that goes the extra mile to get the job done right.   

  bswift has been regularly named one of Chicago’s Best and Brightest Companies to Work For®, as well as one of the Nation’s Best and Brightest Companies to Work For® year after year. We offer a fun, flexible, and creative environment where you can grow both professionally and personally.  

If you have what it takes to join our award-winning culture, we’d love to hear from you!