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.

As the Head of Insights & Operations, you will work closely with the Head of Gusto’s Business team (Chief Operating Officer) and leadership in different organizations to help them effectively run their teams and business areas.

You will flex across both strategic and operational efforts: lead and contribute to strategy, develop and execute on a cross-functional roadmap for Business teams and across Gusto more broadly, deploy effective communications, and design and execute special projects that build new capabilities at Gusto and allow us to meet our collective goals.

To be effective in this role, you must be highly strategic and comfortable with ambiguity. You are an agile and creative problem solver with impeccable communication skills and a bias to action. Building strong relationships  across functions is critical, as you will partner with executive leadership in Gusto’s Business team, their direct reports and across the company, so you must inspire trust by demonstrating excellent judgment and integrity. 

You are as comfortable discussing strategy with a product marketer, or sales effectiveness tactics with an account executive, as you are talking about the needs of our code base with a lead engineer. You excel at leading teams big and small, and you achieve results through influencing others as well as direct ownership of outcomes. Your brand is your intellectual acuity, sharp eye for process improvement, and ability to motivate others to translate insight into action. If this sounds like you - join us at Gusto!

Gusto is committed to creating a diverse and inclusive company where respect and inclusion are the standard. As a policy and as a practice, Gusto provides equal employment opportunity to all applicants without regard to race, religion, belief, color, sex, gender, family care leave status, sexual orientation, gender identity, pregnancy, age, national origin, ancestry, physical or mental disability, medical condition, obesity, military or veteran status, status as a victim of domestic violence, sexual assault, or stalking, genetic information, marital or partnership status, ethnicity, alienage or any other protected classification (together, "Protected Characteristics"), in accordance with applicable federal, state, and local laws.  We also consider qualified applicants with criminal histories, consistent with applicable federal, state and local law.


  • Establish and lead operating processes in the Business organization and within other parts of Gusto. Use cross-functional knowledge to understand issues as well as diagnose trends and perspectives that may influence our internal business partners and our work.
  • Manage 3-year, annual, and quarterly strategic and business planning process in coordination with key business partners. Facilitate communication and decision-making with leaders and teams within the organization and across Gusto. Enable execution of organization wide initiatives.
  • Partner with Finance and HR to effectively allocate and manage headcount and related costs and ensure people and project reporting is maintained.
  • Lead critical projects based on emergent business needs and work collaboratively with partners to deliver results.


Preferred qualifications:

  • MBA or graduate degree in a management, technical or engineering field.
  • 10 years of experience in consulting followed by 6+ years scaling a technology company within operations, strategy or product operations roles with responsibilities of building relationships and leading strategic and operational initiatives.
  • Experience in working with stakeholders across sales, marketing, operations, engineering, product, operations
  • Technical understanding of software as a service business models and technologies
  • Distinctive problem-solving and analysis skills, combined with impeccable business judgment.
  • Comfortable navigating ambiguity.
  • Proven ability to create effective relationships, influence, and collaborate at all organizational levels and with various cross-functional partners.
  • Team-oriented work style.
  • Exceptional problem-solving, strategic, and analytical skills, combined with excellent business acumen.
  • Excellent communication skills, particularly with executive-level stakeholders.

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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