Head of Mid-Market Sales and Business Development

Summary

Join Gusto as the Head of Direct Dedicated Sales and lead our Mid-Market sales team to drive revenue growth. You will develop and execute strategies to enhance customer acquisition, retention, and expansion. This role involves overseeing a team of Account Executives and Business Development Representatives, managing performance, hiring, and development. You will set sales standards, processes, and operations, while also focusing on sales performance reporting and forecasting. The ideal candidate has 10+ years of sales experience with 7+ years managing sales teams, a proven track record of success, and a strong data-driven approach. This remote-friendly position offers a competitive compensation package.

Requirements

• Minimum 10 years relevant sales experience with 7+ years managing sales teams
• Track record growing sales-led businesses in a leadership position including specific contributions and responsibilities for sales talent, tactics, and performance
• High energy, high integrity. Able to motivate and inspire with a track record of building high-performance team cultures
• Proven ability to build a pipeline and achieve revenue targets in a predictable way
• Mathematical mindset with an orientation on repeatability. Excellent at using data to solve problems and drive decision making
• Passion for achieving impact and results that is driven by an entrepreneurial mindset
• A strong communicator (both written and verbal); strong social selling and persuasion skills
• Adaptable sales leader who can upskill teams to deeply penetrate existing partnerships ranging from small to Mid-Market accounts
• Authentic passion for Gusto’s mission and the impact we can have on the world

Responsibilities

• Set and execute the strategic vision for the Direct Dedicated Sales team, ensuring alignment with company-wide revenue objectives
• Empowers high performing sales teams (2nd line leader) focused on acquisition of employers
• Oversees all performance, hiring and development on the teams (Account Executives and Business Development Representatives)
• Manages teams to consistent best practices using data, customer empathy, and sales skill
• Sets the tone and facilitates successful change management
• Collaborates seamlessly with strategy and operations and enablement functions
• Speaks authoritatively regarding team performance and opportunities, cross-functionally and to Sales and Revenue leadership
• Identifies winning sales tactics and collaborates with sales strategy and operations, enablement, compensation, the people team, and finance partners to improve sales performance and contribution
• Sweats the numbers daily, assessing what’s working and not, comparing across Account Executives, Business Development Representatives and teams, identifying trends to amplify or course correct, and working with Account Executives and Business Development Representatives to improve performance
• Runs predictable sales forecasting that aims to drive growth and continuous improvement (vs. solely projecting attainment)

Benefits

• Our compensation range for this role is $212,000 to $270,000 OTE (with a 60/40 split between base salary and target commission) in Denver and most other remote locations, and $232,000 to $307,000 OTE in San Francisco and New York City
• The position can be remote
• Travel will be required (approximately monthly, focusing on Gusto office locations SF, NY, Denver as well as conferences, events, and customer visits