Sales VP

This position is no longer accepting applications(closed Aug 16, 2026).

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!

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What this application asks

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First Name, Last Name, Email, Phone, Resume/CV, Cover Letter

LinkedIn Profile
What is your preferred name? optional
If hired, can you provide proof that you are legally able to work in the United States? choose one
Do you now, or will you in the future, require a visa or any type of immigration sponsorship for work authorization in the country you are working from (e.g., H-1B, OPT, F1, dependent visa)? (if hired, verification will be required consistent with federal law.) choose one
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Are you at least 18 years of age? choose one
Desired Compensation
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Notice to Massachusetts Applicants: It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability. choose one · optional
Notice to Maryland Applicants: UNDER MARYLAND LAW, AN EMPLOYER MAY NOT REQUIRE OR DEMAND, AS A CONDITION OF EMPLOYMENT, PROSPECTIVE EMPLOYMENT, OR CONTINUED EMPLOYMENT, THAT AN INDIVIDUAL SUBMIT TO OR TAKE A LIE DETECTOR OR SIMILAR TEST. AN EMPLOYER WHO VIOLATES THIS LAW IS GUILTY OF A MISDEMEANOR AND SUBJECT TO A FINE NOT EXCEEDING $100. choose one · optional
Are you a current employee of bswift or any affiliates or subsidiaries? (If you are a current contractor or consultant, paid by another employer, then you should answer NO.) choose one
For All Applicants: I certify that I have answered all questions on this employment application truthfully, correctly and completely in accordance with the instructions contained in this application. I further certify that the information provided by me on my accompanying resume, if any, and any other information supplied by me during the application process, is true, correct and complete to the best of my knowledge. I understand that if I failed to provide true, correct and complete information on this application in accordance with its instructions, or in my accompanying resume, this may be cause for the Company to refuse to hire me or, if discovered after I am hired, may be cause for the termination of my employment. I understand that, where permissible under applicable state and local law, I may be subject to a pre-employment drug test after receiving a conditional offer of employment, and I must receive a negative result before being permitted to commence work with the Company. I understand that I may be subject to drug and alcohol screenings, to the extent permitted by law, during the course of my employment pursuant to the Company’s drug and alcohol policy. A positive test result, the alteration or tampering with a test or its results, or my refusal to take the test may result in disciplinary action, up to and including termination of my employment. Smoking is prohibited in all indoor areas of bswift and within 50 feet of the entrance to any bswift facility. I understand and agree that this Application is not an offer of or a contract for employment. I understand that the Application will remain active for 90 Days. After that time, if I desire further consideration by the Company, I will renew my Application in writing or in person. If hired, I understand and agree that I may resign my employment at any time, for any reason and that my employment may be terminated at the will of the Company at any time, for any reason. I further understand and agree that if hired, my wages, hours, working conditions, job assignments, benefits or other compensation will be subject to change at the Company’s discretion. I also understand that any handouts, manuals, policies or procedures maintained by the Company are not contractual in nature and may be amended or abolished at the sole discretion of the Company at any time. To the above statement: Please acknowledge that your on-line consent is equivalent to a binding legal signature; fill in your name here.
Are you currently subject to any Restrictive Covenant agreements that may prohibit you from doing any of the assigned duties of the job in which you are applying? A “Restrictive Covenant” is an obligation owed by the employee to the employer to not do certain things during and post-employment and often include oAn obligation not to work for a competitor of the employer (a non-compete) oAn obligation not to divulge confidential information of the employer (NDA) oAn obligation not to solicit customers of the employer (customer non-solicit) oAn obligation not to solicit other employees of the employer to work somewhere else (employee non-solicit) oAn obligation not to disrupt the relationship of employer with its vendors or customers choose one
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Sales VP

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