Head of Mid-Market Sales and Business Development

About the Role:

Gusto is seeking an experienced Sales Leader with a proven track record in direct sales leadership to drive revenue growth and scale our Direct Dedicated (Mid-Market) Sales organization. This leader will be responsible for developing and executing strategies that enhance customer acquisition, retention, and expansion through our direct sales channel. The Head of Direct Dedicated Sales will oversee a team of Account Executives and Business Development Representatives across the Mid-Market and Dedicated sales segments in the direct sales channel focused on building strong customer relationships and maximizing revenue opportunities.

About the Team:

This role reports into the Head of Subscription Sales, who is empowered by the Head of Revenue (external: Chief Revenue Officer). The team will have 2 sales teams, a Mid-Market / Dedicated Sales team of 11 Account Executives and a Business Development team of (1 PE, 7 Business Development Representatives). The team on day 1 will have approximately 18 team members. 

Here’s what you’ll do day-to-day:

• Sales Leadership

  • 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

• Sales Standards, Process, and Operations

  • Beyond simply leading a sales team, 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 

• Sales Performance Reporting & Forecasting

  • 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)

Here’s what we're looking for:

• 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

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.  Final offer amounts are determined by multiple factors, including candidate experience and expertise, and may vary from the amounts listed above.

Location and Travel

The position can be remote, and travel will be required (approximately monthly, focusing on Gusto office locations SF, NY, Denver as well as conferences, events, and customer visits