VP, Special Markets - PEO

Vestwell is the financial technology company powering the new savings economy. The New York City-based fintech platform redefines how people save for the critical aspects of life across retirement, education, and healthcare savings needs. Today, Vestwell enables over 350,000 businesses and nearly 1.5 Million active savers, with over $30 billion in assets saved across all 50 United States.

Vestwell offers a range of products, including workplace-delivered retirement plans, employer-offered student loan repayment benefits, and various savings accounts for education, emergencies, and individuals with disabilities.

Vestwell's platform serves a diverse clientele, including financial advisers, employers, third-party administrators, financial institutions, payroll providers, government agencies, and individual savers. To learn more, visit

The Vice President of Special Markets is responsible for leading revenue growth through the Professional Employer Organization market, owning strategy, execution, and team leadership for PEO distribution and strategic alliances. This role combines enterprise-channel sales leadership, partner development, and hands‑on deal execution with top PEOs and their internal sales teams. The VP, Special Markets will report to the Divisional Vice President of Special Markets.

Day‑to‑Day, You May Also Be Expected To:

• Develop and own the go‑to‑market strategy for the PEO channel, including target segments, positioning, and multi‑year revenue and growth plans.
• Build, lead, and coach a developing sales organization focused on PEO relationships (e.g., channel managers, partner success, sales engineers as needed).
• Source, negotiate, and close new strategic PEO partnerships while deepening relationships and share of wallet with existing PEO partners.
• Partner closely with marketing to build campaigns, enablement, and jointly owned pipeline targets for PEO executive sponsors and field sales.
• Support sales processes for PEO acquisition and expansion, including account planning, pipeline management, forecasting, and executive deal reviews.
• Establish PEO‑specific KPIs (e.g., active PEO partners, attach rate, plans per PEO, "revenue per seat") and ensure consistent achievement of quarterly and annual targets.
• Collaborate with product and operations to ensure offerings, pricing, and service models are competitive and operationally scalable for PEOs.
• Represent the company with individual PEO C‑suite stakeholders as well as at industry events, positioning the firm as a strategic retirement/benefit and fintech partner.
• Optimize CRM usage and plans that align the team around PEO growth and profitability.
• Provide clear, data‑driven reporting and revenue insights to the executive team and board, including risks, opportunities, and resource needs.

• 10+ years of B2B sales experience, with a minimum of 5 years in a relevant industry (PEO, HRO, and/or Financial Services.
• Proven success selling into PEOs, HROs, or similar employer‑services channels strongly preferred.
• Demonstrated track record of building and scaling enterprise/channel sales teams and consistently exceeding revenue targets.
• Deep understanding of the PEO ecosystem, including decision‑making structures, sales motions, and economics of PEO‑delivered benefits or retirement solutions.
• Experience managing complex, long‑cycle deals with C‑level executives and multiple internal and external stakeholders.
• Strong command of CRM and sales analytics tools, with a disciplined approach to forecasting and pipeline management.
• Exceptional communication, and executive presence, with the ability to influence internally and externally at the highest levels.
• Bachelor's degree or the equivalent combination of education and relevant experience.

This role will be based in Vestwell's NYC office, and will be part of Vestwell's hybrid in‑office operation. For exceptional candidates, we're open to hiring this role fully remote.

The expected base salary range for this position is $110K - $120K base, plus performance based bonus. This position is eligible to participate in the Company Bonus Pool and is eligible to receive new…