Director of Sales

Why Brightside:  

For our clients - our mission is clear. To improve the financial health of working families. Brightside is an employee benefit with a brand-new approach to personal finance. We offer unique solutions to help with anything related to finances, emotions and behaviors that can impact our clients. We take a holistic view to provide unbiased and confidential assistance through an unmatched blend of products, technology and true human care. Our goal is to make it easier for our clients to understand their options to obtain long-term financial health and gain peace of mind when it comes to financial matters.

For our employees - we believe in inspiring careers, a great life/work balance and meaningful work that truly makes a difference in the lives of working families. Your work will have direct impact on the lives of our clients. You will have the opportunity to see a growing start-up from the inside out and see how passionate our employees are about the work we do and the outcomes we are creating for others.

A bit about this role:

We are looking for a mission-driven Director of Sales to bring our message to enterprise prospects as we move into and through a period of rapid growth. You’ll be working alongside our leadership team, closely partnering with our customer success teams to drive seamless (and exciting) launches.  We’re solving complex problems to create meaningful outcomes at Brightside - you will be in the driver's seat of delivering this meaningful mission to so many individuals. Every partnership you forge helps employees reduce stress, gain stability, and unlock opportunities that transform their lives. If you want your sales success to create impact beyond the bottom line, this is the role for you.

• Own the full sales cycle from prospecting to close, for enterprise accounts within your National region.
• Target the largest employers (10,000+ employees) with deal values of $200k+.
• Build and deepen relationships with Benefits, Rewards, HR decision makers, and Benefits Consultants through outbound outreach, social engagement, and industry events/conferences.
• Deliver compelling solution demonstrations that clearly articulate value and ROI, both remotely and in person.
• Challenge the status quo by reframing customer perspectives and industry norms.
• Collaborate cross-functionally, partnering with peers in the sales org and across the business to share insights and influence broader opportunities.
• Develop and manage a healthy pipeline, driving opportunities with purpose, discipline, and accurate forecasting.
• Be the market expert, staying ahead of trends in employee financial health & wellness and positioning yourself as a trusted advisor to clients.
• Own your number by consistently meeting and exceeding personal sales targets and regional goals.

• 3+ years of enterprise sales experience, ideally in a high-growth tech, or startup environment.
• Proven success in complex sales cycles with multiple stakeholders and large-scale deals ($200k+).
• Background in benefits, benefits consulting, HR tech, or fintech strongly preferred.
• Mission-driven mindset with a collaborative, team-first approach to winning.
• Exceptional communication skills with an excellent ability to present an engaging narrative to every level of the buying hierarchy (written, verbally and presentation).
• Comfort in high-velocity environments, balancing urgency with strategic execution.C
• reative and competitive pipeline management, finding new ways to advance deals and close business.
• Adaptability, resilience, and drive to thrive in a fast-changing market.

Employee Benefits at Brightside: 

At Brightside you'll find a remote, safe, fun & inclusive work environment.

We have a competitive benefit plan including generous time off, medical, dental, vision, short/long term disability, life insurance, commuter options and a 401(k) plan.

Equal Employment Opportunity Commission: 

Brightside is an equal opportunity employer and values diversity. We do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.