SupportPay is hiring for an experienced Sr. Enterprise Sales Executive. You will lead revenue growth across HR benefits, financial wellness, and embedded partnerships. We’re pioneering a new category—Modern Family Finances—and looking for a bold, strategic closer to drive deals with employers, brokers, and platforms like EAPs, health plans, and FinTech. If you’ve built sales in a fast-moving, category-defining space and know how to move quickly and creatively to close big deals, let’s talk. Remote | Executive | Financial Wellness | Fast Growth | High Impact

QUALIFICATIONS & EXPERIENCE

• 10+ years of B2B sales experience with a focus on HR benefits, financial wellness or category creators
• Demonstrated success in working with brokers, consultants, and employers of all sizes (from SMB to Enterprise).
• Experience selling a new product category or introducing innovative benefits to the HR market.
• Proven ability to build embedded partnerships with financial wellness platforms, health plans, EAPs, caregiving providers, and benefit aggregators.
• Track record of closing six- and seven-figure deals with complex sales cycles.
• Strong network in the HR, benefits, and financial wellness ecosystem.
• Must be a closer with a creative and aggressive approach to opening doors and closing deals quickly.
• Experience in startup or high-growth environments strongly preferred.

THE ROLE

You’re not just here to “head up sales”—you’re here to build the revenue engine of an entirely new category: Modern Family Finances. SupportPay is rewriting the playbook for employee benefits and financial wellness, and we need a bold, strategic, and relentless dealmaker to turn market interest into market dominance.
This isn’t a “manage the pipeline” kind of role. It’s:
You’ll define go-to-market strategy and get your hands dirty executing it. If you’ve built revenue from zero to scale—and you’re itching to do it again, faster, smarter, louder—this is your seat at the table.
You must be a closer with a creative, fast-moving, and persistent approach to selling. We need someone who can open doors, shorten sales cycles, and close deals quickly while adapting to the needs of a fast-evolving market.

KEY RESPONSIBILITIES

• Sell directly to HR, Total Rewards, Benefits, People leaders and into the broader financial wellness ecosystem (financial platforms, EAPs, Health Plans, etc) educating them on the need for Modern Family Finances as a core component of financial wellness.
• Build strategic partnerships with brokers, consultants, and benefits marketplaces to extend reach and drive referrals.
• Develop embedded distribution channels with platforms including financial wellness platforms, health plans, EAPs, and caregiving providers.
• Collaborate cross-functionally to refine product positioning, pricing, sales enablement, and partner marketing materials.
• Shorten sales cycles, close high-value deals, and build a repeatable growth machine