Health & Benefits - Sr. Sales Executive (Boston, MA)

Location: Home based in the United States; the role is associated with Oak Brook, Illinois, and Boston, Massachusetts, and requires travel to key markets, client meetings, and industry conferences. Relocation is not provided.

Salary: $100,000–$126,000 base per year; OTE $252,000+.

Company

Provides health and wealth solutions, including health savings accounts, automatic rollover services, emergency savings, and custody services, for employers, individuals, and institutional partners.

What you will do

• Build business across national accounts, middle markets, small groups, distribution channels, group insurance, and specialty products.
• Develop influential relationships with brokers, consultants, customers, planning sponsors, and investor communities.
• Manage business development, territory research, marketing, communications, training, competitive analysis, and sales pipelines.
• Lead the complete sales process from prospecting and solution positioning through complex negotiations and closing.
• Coordinate client and internal organizations to support implementation and installation needs.
• Drive cross-selling and maintain Salesforce pipeline records after initial sales contact.

Requirements

• 7–10 years of experience in field sales, account management, benefits consulting, or financial services.
• Bachelor’s degree in Finance, Communications, Business, Marketing, or a related field.
• Business-to-business sales experience with a proven record of successful prospecting and closing.
• Strong consultative selling, negotiation, relationship-building, analytical, organizational, and communication skills.
• Understanding of alternative assets, including hedge funds, fund of funds, private equity and debt, and marketplace lending.
• Ability to travel to key markets and conduct in-person and virtual client meetings.

Nice to have

• Experience with Salesforce CRM.
• Existing relationships across the financial services and benefits industries.

Culture & Benefits

• Home-based work arrangement with collaboration through client and industry meetings.
• Healthcare coverage and a 401(k) savings plan.
• Company holidays, paid time off, and parental leave.
• Employee assistance program.
• Values-led culture focused on compassion, trust, continuous improvement, and collaboration.