Sales VP- Enterprise
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 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, Enterprise.
WHAT YOU’LL DO
The Sales VP, Enterprise is responsible for driving growth within bswift’s enterprise market by selling our technology and services to large, complex employers with 35,000 or more eligible lives. This role owns the full sales cycle, from proactive prospecting and opportunity development through RFP response, solution design, pricing strategy, contract negotiation, and close.
The Sales VP, Enterprise builds relationships with senior decision-makers, including CHROs, CFOs, benefits leaders, procurement executives, IT leaders, consultants, and brokers. Success in this role requires experience navigating complex, multi-stakeholder sales processes, developing tailored benefits administration solutions, and building long-term client and market 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 enterprise employers with 35,000 or more eligible lives.
- Develop and execute targeted sales strategies for complex enterprise prospects.
- Build and maintain relationships with senior client executives, benefits consultants, brokers, enrollment firms, and other strategic partners.
- Proactively prospect within assigned enterprise markets and develop a qualified pipeline of jumbo-market opportunities.
- Lead the full enterprise sales cycle, including discovery, solution development, RFP responses, finalist presentations, pricing, negotiations, and contract execution.
- Assess each prospect’s business, technology, service, integration, communication, and employee experience needs to develop a tailored solution.
- Coordinate internal teams throughout the sales process, including Solution Architecture, Product, Technology, Legal, Finance, Implementation, and Client Services.
- Lead internal strategy and preparation sessions for external sales meetings, presentations, and finalist discussions.
- Create and deliver compelling presentations that clearly communicate bswift’s capabilities, differentiation, and business value.
- Navigate complex buying groups that include benefits, HR, finance, IT, procurement, legal, and executive leadership.
- Manage complex negotiations involving pricing, service models, implementation requirements, performance commitments, and contractual terms.
- Identify opportunities to position bswift’s full portfolio of technology, benefits administration, communication, and related services.
- Develop relationships with key market influencers and maintain a strong presence at industry events and forums.
- Maintain an accurate enterprise pipeline and provide clear visibility into opportunity status, risks, next steps, and projected close timing.
- Partner with internal implementation and client teams to support a smooth transition from sales through contracting and implementation.
WHAT YOU NEED TO SUCCEED
Required Education and Experience
- 10+ years of experience in enterprise sales, strategic sales, or a comparable client-facing growth role.
- Proven success selling benefits administration, HR technology, insurance, or SaaS solutions to large enterprise employers.
- Experience selling to employers with 35,000 or more eligible lives.
- Demonstrated success managing long, complex sales cycles involving multiple business and technical stakeholders.
- Experience developing and presenting solutions to CHROs, CFOs, benefits executives, IT leaders, procurement teams, and other senior decision-makers.
- Strong understanding of benefits administration, enrollment technology, implementation requirements, data integrations, and enterprise service delivery.
- Experience leading complex RFP responses, finalist presentations, pricing discussions, and contract negotiations.
- Ability to translate complex client needs into clear, differentiated solutions and business value.
- Strong public speaking, executive presentation, negotiation, and relationship-management skills.
- Ability to collaborate effectively across Product, Technology, Legal, Finance, Implementation, and Client Services.
- Bachelor’s degree or equivalent professional experience.
NICE TO HAVE
Preferred Education and Experience
- Experience selling SaaS solutions in the People, HR technology, or employee benefits space.
- Established relationships with national benefits consultants, brokers, third-party administrators, or other enterprise-market influencers.
- Experience selling benefits administration solutions to Fortune 500 or similarly complex organizations.
- Experience structuring solutions that include multiple products, services, integrations, and implementation workstreams.
- Familiarity with the operational, compliance, security, procurement, and contracting requirements of jumbo-market employers.
OTHER DUTIES
Please note this job description is not designed to cover or contain a comprehensive listing of activities, duties, or responsibilities required of the employee in this role. Duties, responsibilities, and activities may change at any time with or without notice.
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!
Skills
As published by greenhouse · 18 questions
Basics
First Name, Last Name, Email, Phone, Resume/CV, Cover Letter
Short answers (9)
- LinkedIn Profile
- What is your preferred name? optional
- Please list your current/most recent employer
- What is your current/most recent title?
- Do you want to add a professional license or certification? If yes - please list the current licenses and/or certifications optional
- Desired Compensation
- Website optional
- 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.
- What is your Notice Period?
Pick from a list (9)
- If hired, can you provide proof that you are legally able to work in the United States?
- 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.)
- Are you at least 18 years of age?
- Do you currently work for a bswift Channel Partner?
- 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. 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. 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.)
- 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
- Do you live in one of these states/cities?