VP of Sales

Real is seeking a VP of Sales who will be responsible for driving strategy, implementation, and business development support for the company's employer and broker parties. The ideal candidate will have extensive experience in the employee health benefits industry and will be accountable for identifying and expanding business development opportunities. They will also oversee the sales department and work closely with internal partners to achieve revenue growth. This role requires strong industry relationships, project management skills, and the ability to build rapport at all levels within an organization.

Expand the depth and breadth of Real’s interaction within employer, broker, and consulting community, building out a pipeline of employers and brokers to meet, increasing Real market share by identifying and developing new opportunities within sales, building weekly meeting calendar for the sales team to pitch partners and developing a full strategy to drive revenue growth

Forecast deal flow and architect 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 that align with broader organizational goals

Manage a team inclusive of B2B Marketing, Sales Development, Sales & Account Management, and Customer Success

Create an environment that fosters innovation and creativity by leading with curiosity

Work closely with internal partners including marketing, product, finance, and legal to deliver on Go-To-Market goals

Attend and lead various educational meetings, capabilities presentations and networking events both in person and via conference call

Maintain a high level of comprehension of the market as well as competitive intelligence including, employer benefit consultant/broker needs, market trends, industry challenges, major players, relevant products and technologies

Create a culture of accountability by leading by example

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

Passionate about building a framework for growth to support sales goals and existing clients

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