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!
The Senior Vice President of Direct Sales plays a pivotal role within bswift's direct sales team, driving the growth of technology and service sales to large and mid-market employers. In this executive position, the SVP will lead a team of sales professionals while also personally managing relationships with key external partners. The SVP will oversee the entire sales cycle—from prospecting and lead generation to responding to RFPs, negotiating contracts, and finalizing deals—working closely with internal teams like Solution Architects, Sales Operations and Legal to ensure seamless execution.
The ideal candidate is a dynamic, self-starting leader with deep industry knowledge, a proven track record in sales, and the ability to foster a high-performing sales culture that drives results.
Key Responsibilities:
Sales Leadership: Lead, manage, and mentor a team of sales executives, ensuring the team meets and exceeds regional and national sales targets.
Strategic Sales Execution: Drive proactive prospecting and develop strategies to penetrate large and mid-market employer segments. Ensure the team successfully manages inbound opportunities from distribution channel partners.
End-to-End Sales Management: Oversee the full sales cycle, including response to requests for proposals, pricing strategies, external meeting preparation and execution, and contract negotiation in collaboration with legal teams.
Market Representation: Act as the face of bswift to the marketplace, building influential relationships with key external stakeholders such as employers, consultants, brokers, and enrollment firms.
Growth Strategy: Develop and execute a comprehensive sales and growth strategy that aligns with the company’s business objectives and ensures a strong market presence in targeted regions.
Cross-Functional Collaboration: Partner with Solution Architects, Marketing, sales operations and other internal teams to design and deliver tailored solutions that meet client needs.
Complex Negotiation: Lead the team in managing complex sales negotiations, positioning products and services to meet client demands and exceed revenue targets.
Prospect Partnership: Gain a deep understanding of client needs and recommend appropriate solutions from bswift’s full array of enrollment technology and services, ensuring a value-driven approach to sales.
Industry Leadership: Represent bswift at industry events, market forums, and conferences, positioning the company as a leader in benefits administration.
Performance Monitoring: Track and analyze sales performance metrics, providing regular reports to the executive leadership team and adjusting strategies as needed to ensure success.
Leadership & Team Management:
Build and sustain a high-performing sales team, fostering a culture of accountability, creativity, and collaboration.
Provide ongoing training, coaching, and career development opportunities for sales professionals to ensure continuous growth and high engagement.
Establish clear performance metrics and regularly review team and individual performance to ensure alignment with company objectives.
Inspire and lead the team by example, cultivating an environment of innovation and strategic thinking that drives win/win business outcomes.
Required Experience:
15+ years of sales experience in the benefits administration or insurance industry, with at least 5 years in a senior leadership role.
Proven track record in selling benefits administration, insurance, or related products to large and mid-market employers.
Experience managing complex sales situations involving senior-level executives across employee benefits, procurement, finance, IT, and consulting firms.
Demonstrated success in leading and developing high-performing sales teams in a fast-paced environment.
Executive presence with experience in public speaking and high-level presentations.
Education:
Bachelor’s degree required; advanced degree (MBA or equivalent) preferred.
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 $XX.00-$XX.00, 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!
bswift is an equal opportunity/affirmative action employer.
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.
We are committed to being an equal opportunity and affirmative action employer. All qualified applicants will receive consideration for employment regardless of personal characteristics or status. We take affirmative action to recruit, select and develop women, people of color, veterans and individuals with disabilities.
If you have what it takes to join our award-winning culture, we’d love to hear from you!
