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

Head of Insights & Operations

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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.

Responsibilities

  • 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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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
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
Mental health benefits
Transgender health care 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
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
Professional Development Benefits
Lunch and learns
Promote from within

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