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Lead Executive Assistant

Gusto

Gusto

Administration
Denver, CO, USA
Posted on Saturday, May 25, 2024


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 300,000 businesses nationwide.

Our mission is to create a world where work empowers a better life, and it starts right here at Gusto. That’s why we’re committed to building a collaborative and inclusive workplace, both physically and virtually. Learn more about our Total Rewards philosophy.

About the Role:

The Customer Experience (CX) Executive Assistant/Operations Lead will directly manage two Executive Assistants and work closely with leaders within the Customer Experience organization. This person will operate on a player/coach model where they both empower a team and support leaders within the organization.

They will ensure that the team has strong practices for coordination, execution, communication, and alignment. They will serve as the primary EA to 1-3 leaders within the Customer Experience organization. This person will provide leverage and expertise to the CX Leadership team in order to drive Gusto forward and scale. They will also be a part of the broader Executive Operations community and report directly to the Head of Customer Experience (Head of CX).

Here’s what you’ll do day-to-day:

  • People Empowerer: directly manage two members of our Customer Experience ExecOps Team.
  • Expert of ceremonies: strategically partner to prioritize and coordinate the leader’s time. Make sure it aligns with the priorities of the department, plus creating a system of accountability so that the time allocation can evolve and change as needed. The leader’s time should be prioritized in an intentional and deliberate way. Ideally as proactively as possible, not reactively. Responsibilities include calendar management, including all internal and external meetings.
  • Meeting enabler: organize, attend, and track minutes plus action items with an eye on making every interaction productive and enjoyable. The magic here is in ensuring the right set of follow-up actions are taken and having the relationships in place to follow-up with the stakeholders 1-1 if necessary.
  • Project management: keep multiple teams and projects on track in parallel. Gusto is a 2000+ person organization and how we do planning, and organize x-functional work requires lots of moving parts at times. You will be a key enabler of things moving smoothly, or recognizing when they’re not and making changes to make it smoother.
  • Gifted communicator: represent the leaders well through phone, email, and chat with various internal and external stakeholders.
  • Culture carrier and community builder: Embody Gusto Values while planning team off-sites, team-building events, and connecting the dots between different parts of the Gusto organization.
  • Relationship builder: you’ll be getting to know hundreds of Gusties across the organization, as well as many external individuals. Creating meaningful and memorable interactions should be natural to you, and something that is a source of excitement.
  • Travel planner: flights, hotels, transportation, dining, etc.
  • Special projects: May include research, analysis, presentation preparation, cross-functional company programs, etc. These projects should be executed with quality, but the goal is not to have them become a large percentage of your time.

Here’s what we're looking for:

Work Background:

  • 5+ years of direct administrative experience supporting one or more C-Level executives or General Managers of a Division. Ideally, the organization the executive managed was 1,000+ people, and previous EA work involved working with multiple departments in an organization.
  • 1+ years of management experience, directly managing other EAs.
  • Demonstrated ability to own large x-functional projects from end to end, ideally with visibility to an executive team and/or board of directors.
  • Experience organizing (in-person, remote, and hybrid) team events with anywhere between 10-1000 Gusties, such as an executive offsite or team all hands.
  • Demonstrated ability to organize complex travel schedules with many moving parts, including multiple briefings in one day, managing multiple stakeholders, etc.
  • Experience supporting scheduling with external parties is a plus.

Characteristics & Skill set:

  • Organized and detail-oriented. Able to prioritize multiple assignments and stay calm under pressure, creating order out of chaos. The attention to detail bias must be an intrinsic mindset, and it will be connected to a strong desire to optimize and make things better. The ideal candidate will derive tremendous joy from improving something and crafting the details; inefficiency makes them cringe and drive action to remedy while bringing others along for the journey.
  • Structured Thinking, Structured Mindset. Must have developed a highly structured and efficient means of managing one’s own time, plus have the ability to explain this structure. The foundation should be based on intentional and deliberate prioritization.
  • Excellent Communication Skills and Presence. Ability to communicate the priorities of the leaders to others inside the organization, whether it is by written verbal, or group communications. The ideal candidate will be clear, concise, and kind in their communication and command of a room, meeting, or interaction. They have the ability to adjust their style based on the audience and situation.
  • Natural ability to connect the dots on different ways of communicating and collaborating. The right candidate will have high EQ, read people well, and have a warmth about them when working with people they know well, and also don’t know well. They should be solutions-oriented and find enjoyment in solving problems. They will bring a sense of balance to the team.
  • Confidentiality. Demonstrated ability to maintain complete confidentiality on all business matters, including examples when this resulted in tension.
  • Intellectual curiosity to discover new ways to make things better. This should manifest as a character trait, and include a compulsion to improve things, find new ways of doing things, and drive a desire for lifelong learning. When facing a complex situation, your bias should be to break it down into bite-sized components. Relentless optimization and improvement drives you to learn new things and powers your attention to detail. This requires great memory, and also means that self-improvement is likely a big factor in your life (professionally and personally).
  • Excellence with major productivity suites, especially Google Apps, as well as a demonstrated ability to pick up new tools, evaluate them, weigh the pros/cons, and optimize one’s work style. Should have clear examples of recent productivity tools that were tested out and either kept or disregarded, plus the ability to explain why.
  • Attributes others will have said about you: constantly learning new things, high attention to detail, great memory, calm under pressure, easy to work with, deliberate & intentional with their actions, precise, level headed, calm and collected, cares about the details, crafts their work.

Our cash compensation amount for this role is between $108,000 & $128,000 in Denver and most major metro areas. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.


Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale.

Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas.

When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required.


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.

Gusto 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. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. If you require assistance in filling out a Gusto job application, please reach out to candidate-accommodations@gusto.com.