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!