VP of Sales

Real is seeking a VP of Sales who will be responsible for driving strategy, implementation, and business development support associated with engaging the company's employer and broker parties. The ideal candidate should have extensive experience in the employee health benefits industry and will be accountable for identifying, expanding, scaling, and integrating business development opportunities. They will also oversee the sales department and manage a team inclusive of B2B Marketing, Sales Development, Sales & Account Management, and Customer Success. The VP of Sales will play a crucial role in driving revenue growth and building strong relationships with clients.

• Expand the depth and breadth of Real's interaction within employer, broker, and consulting community
• Build out a pipeline of employers and brokers to meet, increasing Real market share
• Identify and develop new opportunities within sales
• Build a weekly meeting calendar for the sales team to pitch partners
• Develop a full strategy to drive revenue growth
• Forecast deal flow and negotiate creative deals and partnerships
• Represent Real and interact with clients across the US with greater than 1,000 employees
• Actively prospect, build relationships, and secure deals with companies with greater than 1,000 employees
• Build new territories and define metrics and milestones
• Manage a team inclusive of B2B Marketing, Sales Development, Sales & Account Management, and Customer Success
• Create an environment that fosters innovation and creativity
• Work closely with internal partners including marketing, product, finance, and legal
• Attend and lead various educational meetings, capabilities presentations, and networking events
• Maintain a high level of comprehension of the market and competitive intelligence
• Create a culture of accountability
• Manage and oversee Custom Success and Sales departments

• 12-15+ years of experience within the employer healthcare benefit sales and/or consultant/broker space
• Experience building a sales engine from 0-50M in ARR
• Experience selling $XXX,000 contracts
• Deep and strong industry relationships and a network of consultants and brokers
• Ability to maintain strong internal and external networks; leveraging relationships to prospect and close new business
• Strong data chops; ability to distill insights and learnings from large sets of sales data
• Strong project management skills, with an ability and desire to be effective within a fast-paced, fluid environment often with competing priorities
• A proven track record of success with complex and strategic sales or account management
• The ability to energize, communicate and build rapport at all levels within an organization
• Strong project management skills, with a demonstrable ability to corral and manage details in a fast-paced, fluid environment
• Ability and willingness to travel frequently
• Excellent team player and business partner

• Competitive salary, plus equity in an early-stage startup
• 100% company-funded health, vision, and dental insurance
• FSA plans
• Free One Medical membership
• Free Real membership
• $1800 annual mental wellness stipend
• Short- and long-term disability coverage
• Life insurance
• 401(k) retirement plan
• Unlimited PTO
• Four day work weeks (Monday-Thursday)
• Four-week paid sabbatical after five continuous years of work
• Three floating holidays in addition to company-wide federal holidays
• Two weeks of paid time off in the event of losing a loved one
• Competitive paid parental leave and flexible return to work policy
• Flexible working environment
• Remote-inclusive team
• Autonomous work culture
• Professional development opportunities