Sales Leadership, Health Insurance at Gusto

| Greater Denver Area
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About Gusto

Gusto is a modern, online people platform that helps small businesses take care of their teams. On top of full-service payroll, Gusto offers health insurance, 401(k)s, expert HR, and team management tools. Today, Gusto offices in Denver, San Francisco, and New York serve more than 100,000 businesses nationwide.

Gusto is on a mission to provide delightful, modern payroll to businesses everywhere. We’re proud to have built a product that our customers love. One of our best strategies for charging toward this mission is to bring on more customers so that we can aid them in expanding their impact. We are looking for people who are inspired by this mission and would be excited to tell this story to prospective customers. 

Gusto is actively searching for a dynamic and inspiring sales leader to further accelerate Gusto's growth in the SMB space. You will be responsible for driving new revenue by cross selling Gusto’s benefits solution to our existing client base. The pace in Gusto sales is fast and the landscape we’re playing in ever-changing. We’re looking for someone who is motivated by that and who will bring their experience, creativity and passion for empowering sales professionals to the table every single day.

Here’s what you’ll do day-to-day:

  • Lead a sales team of 8-10 benefit advisors with a focus on development and professional growth
  • Coach, motivate and empower the sales team to meet and exceed monthly, quarterly, and annual quotas
  • Cultivate strong sales fundamentals with the benefit advisors, including but not limited to: pipeline management, follow-up and forecasting
  • Help refine and further develop our strategy: scale revenue from both our direct and indirect sales channels in a cost-effective way
  • Measure and report on sales effectiveness against targets and adjust motions and strategies as necessary
  • Partner with our Sales Insights and Operations team to continuously improve team performance through increased effectiveness and efficiency
  • Collaborate with Sales, Marketing, and Product leadership to identify market opportunities, drive leads and pipeline progression, and help shape the product vision and strategy

Here’s what we’re looking for:

  • 4+ years of sales management experience at a high-growth technology company, ideally in health benefits space
  • A leader that inspires their team: Proven ability to build a performance and trust based culture; attract, coach, and retain top talent
  • A competitive spirit who likes to win: Track record of consistently exceeding monthly, quarterly, and annual sales targets
  • 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 rapid growth
  • Experience selling employer sponsored health plans preferred
  • Active Health and Life Insurance license, or the ability to get licensed upon hire
  • Bachelor’s degree preferred
  • This role is based in Denver

Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto.

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Technology we use

  • Engineering
    • JavascriptLanguages
    • RubyLanguages
    • ReactLibraries
    • ReduxLibraries
    • Ruby on RailsFrameworks


1201 16th St, Suite 350 , Denver, CO 80202

What are Gusto Perks + Benefits

Gusto Benefits Overview

We believe in taking care of you...

In order to do the best work of your life, it is important that you are valued and taken care of. At Gusto, we value our employees above all else and are committed to continually seeking out new ways to foster their well-being. Our values drive how we work and also how we design our benefits program.

Volunteer in local community
Friends outside of work
Eat lunch together
Pair programming
Open office floor plan
Dedicated Diversity/Inclusion Staff
Unconscious bias training
Someone's primary function is managing the company’s diversity and inclusion initiatives
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability Insurance
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Wellness Programs
Retirement & Stock Options Benefits
Company Equity
Child Care & Parental Leave Benefits
Child Care Benefits
Generous Parental Leave
Family Medical Leave
Vacation & Time Off Benefits
Generous PTO
Paid Volunteer Time
Paid Holidays
Paid Sick Days
Perks & Discounts
Casual Dress
Commuter Benefits
Company Outings
Free Daily Meals
Game Room
Stocked Kitchen
Some Meals Provided
Happy Hours
Relocation Assistance
Fitness Subsidies
Professional Development Benefits
Diversity Program
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