Gusto
Gusto simplifies HR, payroll & benefits for modern businesses.
Hybrid

Market Development and Small Business Sales Leader

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Gusto is fundamentally changing how the world works by empowering everyone to put people first. Gusto reimagines payroll, benefits, HR, and finance by automating the most complicated, impersonal business tasks and making them simple and delightful.

We’re looking for a passionate, data-driven leader to develop and manage our Small Business and Market Development programs . You will be responsible for planning, organizing, and leading a ~40 person (and growing) sales and success organization. Your leadership will directly help Gusto drive revenue against our annual goals and continue to help enhance our ability to scale our offering to small businesses everywhere. Your entrepreneurship will be a valuable contribution to developing Gusto’s growth strategy, increasing the size and impact of the team and establishing a culture of crisp execution. This role reports directly to our Head of Sales.

You will:

  • Be a key driving force in continuing Gusto’s sales team growth, especially in our small business and market development teams.
  • Create the vision for industry-leading growth in this segment and help our Sales Managers execute in tandem with their teams
  • Build predictable and repeatable sales funnel processes and best practices across multiple teams, including sales development, professional services, and sales enablement/training
  • Partner with cross functional efforts across Sales Ops, Finance, Product, Marketing, and Risk to remove obstacles and close deals
  • Help us solidify and scale the new go-to-market processes, such as outbound selling, account and introducing more trigger-based x-sell and upsell, with marketing and the rest of Sales Leadership

Qualifications

You have:

  • 8+ years of inside sales success, preferably in a high growth company
  • 3+ years of leadership experience, with experience leading a team of sales managers
  • BA/BS Degree
  • (Preferred) Experience in high transaction volume SaaS application or financial services sales
  • Proven ability to work with and influence cross-functional teams and departments in a rapidly growing environment
  • Proven ability to communicate and manage relationships with senior executives
  • Excellent interpersonal, leadership, organizational, and communication skills
  • Extensive experience in a metrics-driven sales organization
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What are Gusto Perks + Benefits

Gusto Benefits Overview

Taking care of our people is just as important as taking care of our customers. We offer competitive total compensation packages with an emphasis on equity, along with many other great benefits, some of which are included below!

Medical, dental, and vision:
Comprehensive medical, dental, and vision benefits, plus a variety of mental health resources.

Time off:
Gusties are encouraged to take the time off they need to continue doing great work.

Inclusive healthcare:
Fertility benefits, parental leave, pregnancy termination, caregiving, gender-affirming surgery, hormone treatments, transgender-inclusive services, and more.

Free meals and refreshments:
If you work at one of our offices, enjoy food, drinks, and snacks— on us. Conversation and community is an added bonus!

Sabbaticals:
Celebrate 5 or 10 years at Gusto and take a month off to recharge.

Stipends:
Take advantage of monthly internet, phone, and wellness stipends. Enjoy commuter or remote work stipends, along with and cash for your Gusto anniversaries!

Culture
Open office floor plan
Employee resource groups
Quarterly engagement surveys
Hybrid work model
Remote work program
Gusto hires in various locations across the United States, including some specific remote locations. Gusto offices operate on a hybrid model, including some work from home days each week.
Diversity
Dedicated diversity and inclusion staff
Diversity employee resource groups
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability insurance
Dental insurance
Vision insurance
Health insurance
Life insurance
Wellness programs
Mental health benefits
Transgender health care benefits
Abortion travel benefits
Financial & Retirement
401(K)
Company equity
Child Care & Parental Leave Benefits
Generous parental leave
Family medical leave
Adoption Assistance
Fertility benefits
Gusto provides a benefit designed to support your unique parenthood journey. The benefit is not health insurance, but rather provides resources to make family forming more accessible to everyone.
Vacation & Time Off Benefits
Generous PTO
Paid volunteer time
Sabbatical
Paid holidays
Paid sick days
Bereavement leave benefits
Office Perks
Commuter benefits
Free daily meals
If you work at one of our offices, enjoy food, drinks, and snacks— on us.
Free snacks and drinks
Fitness stipend
Home-office stipend for remote employees
Mother's room
Professional Development Benefits
Lunch and learns
Promote from within

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