Innovative Portfolio Companies


Gusto (formerly ZenPayroll)
Executive Assistant to the CEO
Do you love being an EA? Do you view the role as being a business builder? Are you eager to help build a company for the long term, work closely with a CEO and executive team, passionate about helping others, highly organized, and excited about the Gusto mission? If so, you might be a fit for the Executive Assistant to the CEO role at Gusto. Josh Reeves is the CEO of Gusto and he needs an organized self-starter who can be nimble in the wild west world of startups and technology, while also bringing scaling experience to the table as Gusto grows from 500 people to over 1,000 in the coming years. Josh will depend on you to ensure that his time is being spent on the most leveraged activities, and you will also be a confidante and trusted partner on topics relating to how the company operates, what areas require the most focus, and what’s working and not working at any point in time. We want someone who has experience working with executives and teams of several hundred people, into the thousands. They should be comfortable giving a speech to 500+ people, managing a high touch executive mtg, and engaging with external partners such as CEOs of public companies and investors managing billions of dollars. Communication skills of all types should be a core strength, as well as ability to build relationships based on empathy plus mutual respect. Superb organization skills, with very high attention to detail, are mandatory. Above all, your approach to the role should be thinking like a business builder.
As EA to the CEO, you’ll be a key member of the CEO team.
The CEO team at Gusto is a small three person team, made up of the CEO, EA to the CEO, and Chief of Staff to the CEO. The CEO of Gusto believes in empowering his team to own their respective projects and programs, and the CEO team as a collective ensures the CEO job is done in the best way possible. You will be a key stakeholder in this process. This includes:
  • Gifted communicator: represent the CEO 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.
  • Master of ceremonies, i.e. owner of the CEO’s time: strategically prioritize and coordinate the CEO’s time. Make sure it aligns with priorities of the business, plus creating a system of accountability so that the time allocation can evolve and change as needed. The CEO’s time should be prioritized in an intentional and deliberate way. Ideally as proactively as possible, not reactively. Responsibilities include CEO calendar management, including all internal and external meetings.
  • Travel planner: flights, hotels, transportation, dining, etc. The CEO at Gusto travels about once a month, so the frequency isn’t very high, but attention to detail will matter to set an example to others.
  • 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, not all of them, and having the relationships in place to follow-up with the stakeholders 1-1 if necessary.
  • 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. The CEO team must maintain time flexibility to adapt to the needs of the organization, ideally in a proactive way (not reactive way).
  • Project management: keep multiple teams and projects on track in parallel. Gusto is a 500+ person organization and how we do planning, and organize x-functional work require 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.
Work Background:
  • 10+ years of work experience, with at least 7 years of administrative experience supporting one or more executives. Ideally the organization the executive managed was 1,000+ people, and previous EA work involved working with multiple departments in an organization.
  • Career EA who loves the profession and wants to stay an EA for the long term.
  • 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 team events with hundreds of people, as well as multi-day events with smaller groups of people, such as an executive offsite.
  • Demonstrated ability to organize complex travel schedules with many moving parts, including dozens of briefings in one day, managing multiple stakeholders, etc.
Characteristics & Skillset:
  • Organized and detail-oriented. Able to prioritize multiple assignments and stay calm under pressure, creating order of out 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. You should have an allergic reaction to inefficiency.
  • 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).
  • Ability to communicate the priorities of the CEO to others inside the organization, whether it is by written verbal, or group communications.
  • Must have developed a highly structured and efficient means of managing one’s own time, plus have the ability to explain this structure. Foundation should be based on intentional and deliberate prioritization.
  • Curiosity to understand project/program management philosophies, study the theory and best practices, as well as originate new philosophies based on one’s day to day work.
  • Demonstrated ability to maintain complete confidentiality on all business matters, including examples when this resulted in tension.
  • 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 ability to explain why.
  • 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 put people at ease, especially more junior members of the organization who might be intimidated to interact with the office of the CEO.
  • 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 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 makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto. 

About Gusto

Gusto's mission is to create a world where work empowers a better life (what we believe). Gusto has built the first modern all-in-one people platform, bringing together Payroll + Benefits + HR + Employee Onboarding, under one roof. The company processes tens of billion of dollars in payroll, and serves over 60,000 businesses nationwide (which represents over 1% of all employers in America). Customers love the product (NPS of 70+) and spread the word on social media. The company has over 500 employees and is located in San Francisco & Denver. Gusto is funded by Google Capital, Kleiner Perkins, and General Catalyst, as well as the CEOs/Founders of Instagram, Stripe, Nest, PayPal, Yelp, Mint, Shopify, Yahoo, Thumbtack, Dropbox, and Eventbrite, among others

Get to know Josh better

In 2015, Josh gave a talk at Stanford (video link). It touches upon Josh’s journey and how Gusto was started. In addition, below are some articles Josh has written about Gusto’s philosophy and approach.

Job Location(s):
San Francisco, CA, US
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