Job Application for Enterprise Sales VP at bswift

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!

Position Overview:
The Enterprise Sales, VP is responsible for selling bswift’s technology and services to large enterprise employers. This role focuses on proactive prospecting and relationship management with senior decision-makers, including CHROs, CFOs, and other C-suite executives, as well as external partners such as consultants and brokers. The VP will own the entire sales process, from lead generation and RFP response to pricing strategy, contract negotiation, and deal closure.

Success in this role requires a deep understanding of complex sales cycles, creative solution design, and an ability to deliver business value that resonates with large-scale enterprise clients.

Key Responsibilities:

Represent bswift’s technology and benefits administration services to large enterprise employers.
Build and maintain relationships with senior executives, consultants, brokers, and other external third parties.
Develop and execute high-impact sales strategies tailored to enterprise clients.
Lead the RFP response process, collaborating with internal Solution Architect teams to create compelling proposals.
Drive sales meetings, including preparation, external presentation, and follow-ups, ensuring alignment with customer needs.
Own the end-to-end sales process, from opportunity identification and pipeline management to pricing strategy and contract negotiations, in collaboration with legal teams.
Establish a strong market presence within the enterprise sector, including participation in key industry forums and cultivating relationships with key influencers.
Lead complex negotiations, positioning bswift’s products and services to maximize revenue and growth opportunities.
Leverage the full bswift product portfolio to deliver tailored solutions that address the unique needs of large enterprise clients.

Required Skills & Experience:

10+ years of experience in enterprise sales, ideally in benefits administration or SaaS sales to Fortune 500 or large corporate clients.
Proven track record of managing long sales cycles with large organizations and navigating decision-making processes involving multiple stakeholders (CHRO, CFO, IT, etc.).
Deep knowledge of employee benefits administration and related technologies, along with strong expertise in complex negotiations and closing high-value deals.
Experience working closely with cross-functional teams, including legal, finance, and IT, to facilitate smooth sales processes.
Excellent public speaking and presentation skills, with the ability to influence senior-level executives.

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 $160,000-$180,000, 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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Enterprise Sales VP

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