Sales Director (Direct Sales)

Gusto, Denver

It’s time to tame the chaos of payroll, benefits, and HR.

Gusto is seeking a Direct Sales Leader in our Denver office, dedicated to driving Gusto's growth in the SMB space through increasing the number of customers using the full Gusto suite - HR, payroll, and benefits.  He/she will be responsible for net new revenue from our larger “Full Gusto” customers, as well as up selling our existing payroll customers to move their benefits to Gusto. The Direct Sales Leader will also help hire, train, and coach our HR, Payroll, and Benefits Advisors to be a world-class consultative acquisition team.  The pace of Gusto sales is fast and the landscape we’re playing in ever-changing. We’re looking for someone who is motivated by that and brings a good sense of humor to a team that likes to work hard and have fun while we’re doing it.

Here’s what you’ll do day-to-day:

  • Lead a sales team of 8-10 individuals with a focus on development and professional growth
  • Help refine and further develop our strategy: 10x revenue from our Direct Sales team in a cost-effective way
  • Grow net new business within Direct Sales
  • Build a world-class consultative sales team: Invest in and develop the existing sales team while simultaneously attracting top sales talent to Gusto
  • Track, measure and report-out on sales effectiveness against targets and adjust programs and strategies as necessary
  • Scale with rigor: Continuously increase the effectiveness of our team, recognizing opportunities for creating new systems, structures, and processes
  • Work cross-functionally: Flow easily across multiple teams to ensure internal messaging alignment, operational coordination and evangelization of sales strategy; collaborate with marketing to ensure the execution of programs and events to drive leads, pipeline, and deal progression
  • Ensure executive alignment and relationship building between Gusto and partner executive teams

Here’s what we’re looking for:

  • 5+ years of sales management experience: Extensive experience developing sales teams at a high-growth technology company, ideally in the HR, payroll, benefits, or fin tech space
  • A strategic mindset: Ability to think strategically, crisply synthesizing market research and competitive intelligence and turning that into a winning go-to-market strategy
  • A people leader that team members will walk through walls for: Proven ability to coach, attract, and retain amazing sales talent
  • An amazing communicator: Excellent communicator internally and externally
  • A competitive spirit who likes to win: Track record of consistently exceeding established revenue goals
  • Based in Denver, but willing to travel to San Francisco with some frequency
  • A lover of change: Experience managing change and ambiguity, taking ownership and creating structure
  • A fan of speed: Ability to successfully operate in a fast paced dynamic environment experiencing growth and expansion
  • Bachelor’s degree preferred


About Gusto


Gusto offers payroll, benefits, and workers’ compensation to small businesses across the United States, from bike shops in Virginia to tech startups in San Francisco. Our investors include top venture capital

About Gusto

We are Gusto Founded in 2011, Gusto provides payroll, benefits and HR to modern companies. We have offices in San Francisco and Denver, but thanks to our 40,000 small business customers and their employees, there’s a little piece of us in all 50 states. We believe that humans aren’t resources. When we come to work, we don’t leave our humanity at the door. We bring life with us: our feats and friendships, our adventures and aspirations. Great businesses treat us like people, not ID numbers. When that happens, work becomes a source of energy rather than fatigue. It creates a virtuous cycle where life improves work, and work improves our lives. That’s why we started Gusto. Our mission is to create a world where work empowers a better life.

Want to learn more about Gusto? Visit Gusto's website.