About Gusto

Our Head of Gusto team is looking for a strategic partner. You’ll join a world-class strategy and business operations team, balancing strategy, operations, and special projects to create a world where work empowers a better life. This role will focus on projects and programs that span across the customer segments we serve.

You are a creative systems thinker obsessed with operational efficiency. You have strong business acumen and are known for building operational processes, tools and programs that increase efficiency, efficacy and delight. You are looking to round out your experience by working closely with a cross-functional leadership team, including the CEO, CFO and Chief Product Officer. Your insights will enable us to 1) implement and improve programs to drive outcomes across customer segments we serve, and 2) optimize internal operations to track and improve execution. 

We’ll count on you to dive deep to solve our hardest business problems -- from diagnosing issues to devising recommendations to influencing and executing to get it done. You will work across functions, including People, Legal & Compliance, Finance, Revenue and Customer Experience teams and more to better understand friction points in our business, solve them, and build for scale. You will dive into top company priorities, build and execute on plans, and improve operational efficiency at every turn.

As a core member of the CEO (Head of Gusto) team, you will be a key owner of processes for strategic planning and decision making, budgeting, operations, and metrics. You’ll help ensure that Gusto processes run effectively and that we drive results to plan with accountability. 

We’re looking for a force multiplier. Does this sound like you? Read on!

Here’s what you’ll do:

  • Develop and execute planning processes, ensuring coordination with corporate planning processes as well as planning integration across the broader organization.
  • Quarterback the company's rhythm of business (ROB). Works with cross-company/team counterparts to manage team participation as needed for key business events, next fiscal year planning, running business reviews, and other strategic business planning activities. 
  • Be the first point-of-contact for all Ops Cadence questions including logistics, templates/agenda, tooling, etc.
  • Partner with Finance, Business Operations, Executive Ops to drive planning, as well as report on performance vs. plan along our key performance indicators - you will help drive clarity re: whether we are delivering on company goals.
  • Role model outstanding program management and change management skills across Gusto; leverage these skills to organize and enable Gusto leaders to deliver a busy workload on time, with strong outcomes
  • Spearhead the right tools, processes and procedures to support efficient operations in an increasingly remote/hybrid work environment.
  • Deep dive into special projects, dig into root causes, and collaborate across teams to drive sparkling execution. Success means you’ll comfortably navigate the interplay of product/technical teams AND can speak to what a customer-facing CX/Sales Gustie’s day-to-day interactions look like.

Here’s what we’re looking for:

  • 10+ years of relevant work experience in program management, operating or biz ops roles at rapidly growing or scaled startups, and/or consulting with business problem solving training
  • Leaders who deeply understand the art and science of program management and business operations. 
  • Proven process improvement experience and love making things more efficient - arranging tough problems into digestible pieces is intuitive to you
  • Specialty is creating right-sized process and strategic programs from the ground up, using the right home-grown or vendor tools to deliver impact with efficiency - and a penchant for developing strong, effective communications so all stakeholders are brought along the journey
  • Culture carrier: Passionate about people empowerment, boosts team morale when things get tough, and recognized mentor and leader; effectively influences and adds value without authority across all levels of every organization you’ve joined
  • Deep empathy and obsession for our small business customers
  • Grit, hustle, and ability to flex into problems at all altitudes 
  • A deep passion for helping others
  • Experience with new product strategy and market segmentation a plus

Our cash compensation amount for this role is targeted at $156,000 - $197,000/year in Denver & most remote locations, and $184,000 - $220,000/year for San Francisco & New York. Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.

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 with us.

Our company is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Our company considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. We are also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. If you need assistance or an accommodation due to a disability, you may contact us at accommodations@gusto.com. 

Apply for this Job

* Required


Voluntary Self-Identification

Our customers come from all walks of life and so do we. We hire people from a wide variety of backgrounds, not just because it’s the right thing to do, but because it helps us to build better products, better serve our customers, and makes our company stronger. 

In addition to the information required to consider your application, below is a set of voluntary demographic questions. If you choose to fill them out, the responses will be used to help us identify areas for improvement in our process and further support the development and execution of our diversity efforts and programs. 


Your responses to these questions will be recorded and maintained in a confidential file. Your responses, or your choice to not respond,  will not be associated with your specific application and will not in any way be used in making any employment decisions, including hiring decisions.

Please use this as a reference while completing the disability self-identification:

You are considered to have a disability if you have a physical or mental impairment or medical condition that substantially limits a major life activity, or if you have a history or record of such an impairment or medical condition. Disabilities include, but are not limited to: 

  • Blindness
  • Deafness
  • Cancer
  • Diabetes
  • Epilepsy
  • Autism
  • Cerebral palsy
  • Schizophrenia
  • Muscular dystrophy
  • Bipolar disorder
  • Major depression
  • Multiple sclerosis (MS)
  • Missing limbs or partially missing limbs
  • Post-traumatic stress disorder (PTSD)
  • Obsessive compulsive disorder
  • Impairments requiring the use of a wheelchair
  • Intellectual disability


How would you describe your gender identity (please select one)? (Select one)

I identify as transgender (please select one): (Select one)

I identify my sexual orientation as (please select one): (Select one)

I identify my race/ethnicity as (mark all that apply):

Veteran Status (please select one): (Select one)

I have a disability (please select one): (Select one)

I identify as a first-generation professional (please select one): (Select one)