{"id":2949281,"url":"https://alion.io/job/bswift-sales-vp-enterprise","title":"Sales VP- Enterprise","company":{"id":8031,"name":"bswift","domain":"bswift.com","url":"https://alion.io/company/bswift","size_band":"501-1000","is_staffing_agency":false,"employer_type":"direct","is_intermediary":false,"listed_via":null,"ats_vendor":"Greenhouse","truth_index":null},"role":"Sales","role_family":"Sales","seniority":"head","employment_type":null,"work_mode":"remote","remote_scope":"stated_countries","remote_scope_basis":"board_field","remote_working_hours":{"label":"CT","utc_offset_min":-6,"utc_offset_max":-6},"hiring_geo_confidence":"structured","locations":[],"countries":[],"hiring_countries":["US"],"hiring_countries_total":1,"salary":{"min":150000,"max":175000,"currency":"USD","period":"year","gross":null,"usd_annual":175000},"salary_estimate":null,"experience_years_min":10,"visa_sponsorship":false,"relocation_package":false,"has_equity":false,"technologies":[],"status":"live","first_seen_at":"2026-10-20T15:53:25Z","employer_posted_date":"2026-10-20","last_verified_at":"2026-11-11T05:31:03Z","board_verified":true,"closed_at":null,"days_open":21,"trust":{"level":"ok","repost_count":null,"flags":[],"days_open":21},"description":"Want to be a bswifter? \nAt 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. \n 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! \nABOUT US\nbswift 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.\nWHAT YOU’LL DO\nThe 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.\nThe 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.\nWHAT YOU WILL BE RESPONSIBLE FOR\nEssential Functions\nReasonable accommodations may be made to enable individuals with disabilities to perform these essential functions.\nRepresent bswift’s technology and benefits administration services to enterprise employers with 35,000 or more eligible lives.\nDevelop and execute targeted sales strategies for complex enterprise prospects.\nBuild and maintain relationships with senior client executives, benefits consultants, brokers, enrollment firms, and other strategic partners.\nProactively prospect within assigned enterprise markets and develop a qualified pipeline of jumbo-market opportunities.\nLead the full enterprise sales cycle, including discovery, solution development, RFP responses, finalist presentations, pricing, negotiations, and contract execution.\nAssess each prospect’s business, technology, service, integration, communication, and employee experience needs to develop a tailored solution.\nCoordinate internal teams throughout the sales process, including Solution Architecture, Product, Technology, Legal, Finance, Implementation, and Client Services.\nLead internal strategy and preparation sessions for external sales meetings, presentations, and finalist discussions.\nCreate and deliver compelling presentations that clearly communicate bswift’s capabilities, differentiation, and business value.\nNavigate complex buying groups that include benefits, HR, finance, IT, procurement, legal, and executive leadership.\nManage complex negotiations involving pricing, service models, implementation requirements, performance commitments, and contractual terms.\nIdentify opportunities to position bswift’s full portfolio of technology, benefits administration, communication, and related services.\nDevelop relationships with key market influencers and maintain a strong presence at industry events and forums.\nMaintain an accurate enterprise pipeline and provide clear visibility into opportunity status, risks, next steps, and projected close timing.\nPartner with internal implementation and client teams to support a smooth transition from sales through contracting and implementation.\nWHAT YOU NEED TO SUCCEED\nRequired Education and Experience\n10+ years of experience in enterprise sales, strategic sales, or a comparable client-facing growth role.\nProven success selling benefits administration, HR technology, insurance, or SaaS solutions to large enterprise employers.\nExperience selling to employers with 35,000 or more eligible lives.\nDemonstrated success managing long, complex sales cycles involving multiple business and technical stakeholders.\nExperience developing and presenting solutions to CHROs, CFOs, benefits executives, IT leaders, procurement teams, and other senior decision-makers.\nStrong understanding of benefits administration, enrollment technology, implementation requirements, data integrations, and enterprise service delivery.\nExperience leading complex RFP responses, finalist presentations, pricing discussions, and contract negotiations.\nAbility to translate complex client needs into clear, differentiated solutions and business value.\nStrong public speaking, executive presentation, negotiation, and relationship-management skills.\nAbility to collaborate effectively across Product, Technology, Legal, Finance, Implementation, and Client Services.\nBachelor’s degree or equivalent professional experience.\nNICE TO HAVE\nPreferred Education and Experience\nExperience selling SaaS solutions in the People, HR technology, or employee benefits space.\nEstablished relationships with national benefits consultants, brokers, third-party administrators, or other enterprise-market influencers.\nExperience selling benefits administration solutions to Fortune 500 or similarly complex organizations.\nExperience structuring solutions that include multiple products, services, integrations, and implementation workstreams.\nFamiliarity with the operational, compliance, security, procurement, and contracting requirements of jumbo-market employers.\nOTHER DUTIES\nPlease 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.\nWhy Join bswift?\nAt 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.\nBenefits of Working at bswift:\nComprehensive Health Benefits: Access to health, dental, and vision plans to support your wellness and that of your family.\nCompetitive Compensation: A compensation package that recognizes your skills, experience, and contributions, including performance-based incentives for most roles.\nRemote first, Office friendly environment! No time to commute? No problem!\nRetirement Savings Plans: Options to help you plan for a secure financial future with employer-sponsored retirement savings programs.\nProfessional Development: Opportunities for career growth, including training and access to resources to support your career progression.\nSupportive Culture: A work environment that encourages collaboration, open communication, and creative problem-solving, where your voice and ideas are valued.\nEmployee Wellbeing Initiatives: Programs focused on mental health, financial planning, and wellness resources to help you thrive inside and outside of work.\nMake 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.\nSpecific benefit offerings vary by position and may be subject to change.\nStandard working hours are 8am-5pm Central Time, unless otherwise stated in the Job Description. \nIn 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!\nAt 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. \n 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. \nIf you have what it takes to join our award-winning culture, we’d love to hear from you!","description_format":"text","description_chars":9740,"description_truncated":false,"requirements":{"experience_years_min":10,"management_years_min":null,"team_size_min":null,"manages_managers":false,"education":{"level":"bachelor","optional":false},"security_clearance":false,"languages":[]},"benefits":["Equity","Professional development","Retirement plans"],"hiring_locations":[{"name":"United States","iso":"US","kind":"country"}],"hiring_excludes":[],"relocation_offered":false,"industries":["Human Resources","HR & Recruiting AI","Health Insurance & Benefits","HR & Payroll Software"],"lifecycle":[{"event":"open","at":"2026-10-20T19:30:09Z"}],"visa":[],"liveness":{"score":64,"band":"ok","label":"Likely open","p_open":1,"p_active":0.847,"p_room":0.75,"age_days":21,"expected_fill_days":26,"reasons":["conf:0","win:late"],"computed_at":"2026-11-11T05:49:22Z"},"pay":{"stated_usd_annual":175000,"is_top_pay":false},"html_url":"https://alion.io/job/bswift-sales-vp-enterprise","json_url":"https://alion.io/job/bswift-sales-vp-enterprise.json","meta":{"generated_at":"2026-11-11T09:42:45Z","cache_seconds":300,"methodology":"https://alion.io/methodology","terms":"https://alion.io/terms","contact":"https://alion.io/contact","api":"https://alion.io/developers","about":"Alion is a live layer of people, companies and AI agents: who they are, whether they are real and active right now, what they do and how to work with them, readable by people and by agents and paid per call.","catalog":"https://alion.io/catalog.json","usage":{"tier":"crawler_verified","counted_by":"address","units_charged":1,"used_today":16263,"day_limit":null,"remaining_today":null,"minute_limit":300,"resets_at":"2026-11-12T00:00:00Z"}},"offers":[{"id":"company.slices","title":"One company in depth, by slice","status":"live","price":{"credits":0.1,"usd":0.01,"plus_per_slice":{"credits":0.05,"usd":0.005}},"unit":"per company, plus each slice with data","note":"the employer in depth","call":{"mcp_tool":"get_company","arguments":{"id":8031},"rest":"https://alion.io/mcp/rest/get_company?id=8031"},"human":"https://alion.io/catalog?offer=company.slices&for=job%2Fbswift-sales-vp-enterprise"},{"id":"market.stats","title":"A market slice: pay, demand and time to fill","status":"live","price":{"credits":2,"usd":0.2},"unit":"per slice","note":"pay, demand and time to fill for this role and place","call":{"mcp_tool":"market_stats"},"human":"https://alion.io/catalog?offer=market.stats&for=job%2Fbswift-sales-vp-enterprise"},{"id":"job.search","title":"Open jobs by role, technology, place, pay and visa","status":"live","price":{"credits":0.1,"usd":0.01},"unit":"per posting in a list","note":"similar open postings","call":{"mcp_tool":"search_jobs"},"human":"https://alion.io/catalog?offer=job.search&for=job%2Fbswift-sales-vp-enterprise"},{"id":"company.verify","title":"Is this company real and active right now","status":"pilot","price":null,"unit":"per company","request":{"url":"https://alion.io/catalog/request","method":"POST","body":"{\"offer\": \"company.verify\", \"for\": \"job/bswift-sales-vp-enterprise\", \"note\": \"what you need it for\"}"},"human":"https://alion.io/catalog?offer=company.verify&for=job%2Fbswift-sales-vp-enterprise"}],"agent":{"mcp":"https://alion.io/mcp/jobs","mcp_open":"https://alion.io/mcp/open","next":[{"tool":"get_job","arguments":{"id":2949281}},{"tool":"search_jobs","arguments":{"company":"bswift.com","detail":"compact"}},{"tool":"match_people","arguments":{"job_id":2949281},"note":"people open to offers who fit this vacancy"}],"note":"The same data through MCP tools: https://alion.io/mcp/open needs no sign-in (compact searches, postings, people); https://alion.io/mcp with an Alion account has everything. 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