Senior Account Executive - Broker Channel/Enterprise
When
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AE Broker or Ent
About When
Description
Account Executive - Broker Channel
Account Executive - Enterprise
About When
When is a venture-backed, US-based technology company transforming the way companies offboard employees. Our AI-powered health insurance marketplace and post-employment platform help employers reduce COBRA costs and support employees through career transitions. We’re solving a critical gap in the employee lifecycle with innovative tech and a people-first approach.
The Opportunity
We’re looking for two seasoned Senior Account Executives (Broker Channel or Enterprise) as we grow our sales organization. Reporting to our CEO, these are foundational roles in our go-to-market strategy—ideal for a self-starter who thrives in a fast-moving environment and wants to shape the future of our sales engine.
As an early hire, you’ll partner closely with leadership, marketing, and product to drive new business, refine our sales playbook, and help scale a game-changing solution in the HR/benefits space.
What You’ll Do
Own the Full Sales Cycle
- Prospect, pitch, and close new business across mid-market and enterprise accounts
- Conduct consultative discovery calls and product demos with HR leaders, brokers, and key decision-makers
- Manage complex deals and multiple stakeholders through long sales cycles
Build and Expand Relationships
- Serve as the primary point of contact for clients in your book of business
- Identify upsell and cross-sell opportunities
- Collaborate with the Client Success team to ensure smooth onboarding and retention
Collaborate Cross-Functionally
- Work with Marketing on targeted campaigns and lead generation strategies
- Partner with product and engineering to share client feedback and influence roadmap
- Represent When at industry events and conferences
Manage Your Pipeline Like a Pro
- Keep Hubspot CRM fully updated with activity and opportunity details
- Maintain a healthy pipeline and accurate forecast
- Share insights and trends with leadership to help inform strategy
Who You Are
- 7+ years of B2B SaaS sales experience in HR tech or benefit administration
- Must have existing relationships with benefit brokers and/or decision-makers at enterprise companies in the HR Tech/employee benefits space
- Proven track record closing enterprise client deals
- Experience selling in HR tech, payroll, benefits, or related industries
- Strong background in HR tech, employee benefits platforms, PEOs, TPAs, payroll, or healthcare
- Skilled in virtual selling, managing long sales cycles, and building C-suite relationships
- Proficient in Hubspot, Salesforce and sales tools such as ZoomInfo
- Strong communicator, both written and verbal
- Highly organized, self-motivated, and excited about building something from the ground up
- Comfortable in a fast-paced, high-growth startup environment
- Must have existing relationships with benefit brokers, channel partners, or HR buyers
- Experience in a startup or early-stage sales environments and comfortable or high-growth environment where processes are still being built
- Success in launching new markets or territories
Compensation & Perks
- Competitive base salary + uncapped commission
- 100% company-paid health insurance
- Opportunity to shape a category-defining product
- Collaborative, mission-driven team
Travel Requirement: Approximately 25-30% for customer meetings, conferences or other events.
This job is no longer accepting applications
See open jobs at When.See open jobs similar to "Senior Account Executive - Broker Channel/Enterprise" B Capital.