Head of Sales

Head of Sales SupportPayLocation : Remote (U.S. Preferred)Type : Full-Time, ExecutiveAbout SupportPaySupportPay is the leading platform pioneering Modern Family Financial Management, transforming how families split, track, and share financial responsibilities across households. As the first and only solution addressing the intersection of family and financial stress, SupportPay helps employers enhance employee financial wellness, reduce absenteeism, and increase productivity.Our mission is to eliminate family fights over money by providing a structured, transparent, and conflict-free financial solution for modern families. We are now looking for a dynamic Head of Sales to drive revenue growth, accelerate adoption, and expand our footprint in the HR benefits and employer market.The RoleWe are seeking a strategic and hands-on Head of Sales who will lead SupportPays sales efforts, drive revenue growth, and expand partnerships with employers, brokers, and benefits consultants. This role requires a sales leader with a deep network of HR benefits professionals, experience in category creation sales, and a strong ability to drive pipeline growth from enterprise-level employers and benefits firms.The ideal candidate is a closer and a builder, with a proven track record in selling innovative solutions to HR and benefits leaders. They should be comfortable working in a high-growth, fast-paced startup environment.Key ResponsibilitiesDevelop and execute the sales strategy to drive revenue growth across enterprise employers, brokers, and benefit consultants.Build and manage the sales pipeline, focusing on key HR benefits decision-makers.Leverage an existing network of HR, benefits, and compensation professionals to accelerate deal flow.Lead prospecting efforts and direct sales initiatives, driving outbound engagement and closing high-value deals.Own the full sales cycle, from lead generation and qualification to negotiation and deal closure.Partner with marketing to refine messaging and ensure alignment with demand generation strategies.Collaborate with the CEO and executive team to refine pricing models, sales strategies, and market positioning.Develop key relationships with benefits brokers, consultants, insurance carriers, and HR executives to drive strategic partnerships.Recruit, manage, and mentor a high-performing sales team as the organization scales.Qualifications & Experience10 years of sales experience, with 5 years in a leadership role focused on HR benefits, employee wellness, or financial wellness solutions.Deep, established network of HR benefits leaders, brokers, and consultants (this is critical for success).Experience selling a new category of product or pioneering an industry segment.Proven track record of closing six- and seven-figure B2B enterprise deals.Hands-on sales leader with the ability to develop and execute strategies while also directly selling.Ability to navigate long sales cycles and articulate the ROI of an innovative benefit to HR decision-makers.Experience with selling benefits solutions to large enterprises (5,000 employees).Strong analytical mindset with a focus on data-driven decision-making.Startup or high-growth company experience preferred.Why Join SupportPay?Be part of a mission-driven company transforming the way families manage financial responsibilities.Work directly with the CEO and executive team to shape the future of the company.Make an immediate impact in a fast-growing, high-potential market.Uncapped earning potential with competitive base salary, commission, and equity options.Join a company that is recognized as an innovator, having won awards from Panasonic Well, AARP AgeTech, and other leading organizations.If youre a sales leader with a deep HR benefits network and experience selling a category-creating solution, we want to hear from you!

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