Gusto

Chief of Staff to the CEO

Do you aspire to be a CEO someday? Are you an experienced operator who wants to work x-functionally with the span of an entire company as your next professional chapter? If so, you might be a good fit for the Chief of Staff role at Gusto. The expectation is that this is a ~24 month position, and you will graduate into a senior operating role at Gusto afterwards. Josh Reeves is the CEO of Gusto and he’s looking for someone who can be a sounding board to him, a confidante, and a partner in helping Gusto scale as the company grows from 500 people to over 1,000 in the coming years, while serving over 1% of all companies in America. You will be his right hand person and get exposure to all aspects of running a company of Gusto's size and scale. The right candidate will have built significant teams, run planning processes, set business direction, and worn many hats in the scaling of their organization. They should be familiar working with executives (or be an executive themselves), and be able to fill in for Josh when he needs to be in two places at the same time. They should be comfortable giving a speech to 500+ people, managing a high touch executive meeting, 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 strong relationships based on empathy plus mutual respect. Superb organization skills, with very high attention to detail, are mandatory.

⇒ For reference, you’re encouraged to read the First Round Review article about the Chief of Staff role.

As Chief of Staff, 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. 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:

Ad-Hoc Projects:

The CEO role at a start-up includes gap filling for special projects across the organization. As a force multiplier of the CEO, you will be involved in a variety of projects spanning all parts of Gusto.
These projects could include government and policy relations, location based campaigns, internal Gustie initiatives, new market explorations, leading a team for a few months before a new leader is found, and more. Basically the things that are most important and/or requiring the CEOs time will be the things you are involved with.
In addition, you will frequently collaborate with other Gusto teams focused on Investor Relations, Business Development, FP&A, Corporate Development, and more.

Board & Investor Coordination:

Serve as a primary liaison between Gusto and its Board of Directors.
Project manage Board meeting prep and creation of Board meeting materials.
Provide regular written updates to the Board on key business moments and progress against goals.
Work with Gusto’s finance team to provide updates to investors as needed.

Facilitate Gusto Executive Team:

Gusto’s executive team is made up of the CEO, COO, CFO, CTO, Chief Product Officer, and Chief People Officer.
Provide a bridge for smooth communication between the the CEO and execs across Gusto, enabling effective x-functional collaboration across the organization.
Provide decision support through research, analysis of information, and clear presentation of considerations.
Successfully complete critical aspects of deliverables with a hands-on approach, including drafting correspondence, and other tasks that facilitate the CEO's ability to effectively execute on top priorities.

Executive & External Communications:

Work with the CEO and Gusto’s PR & Communications team to prioritize inbound speaking and interview requests for the CEO.
Prepare presentations for internal and external audiences. This involves facilitating the setting of topics for company-wide meetings, helping to prepare speakers from across the company, as well as owning other communications such as the CEO newsletter.
In the situations where the CEO has two commitments, you’ll counsel him on which path to take, and then fill in for him at the second commitment.

Your Work Background:

Bachelor’s degree and MBA a plus.
10+ years of relevant operating experience, with experience building teams (ideally larger than 100 people), owning goal setting, hitting targets, hiring/firing, getting leverage from a group, etc.
Experience managing complex, multi-location strategies, projects and operations.
Significant x-functional project experience, working with many stakeholders, across departments, etc.
Operating experience in two different departments ideal (ex. Sales & Marketing, ex. Product & Operations).

Your Characteristics & Skillset:

Natural executive presence and comfortable working with senior leaders.
Strong opinions based on experiences and belief in what the future looks like, plus framework approach to iteration and experimentation to make that future become real.
Structured thinker with strong bias to problem solving.
Able to disagree and commit.
Extreme growth mindset, driven by intense curiosity.
Detail-oriented organizational and process management skills to manage a wide range of incoming requests and responsibilities. Ability to create order out of chaos.
Hyper-organized but also flexible. Outstanding execution skills.
Emotional intelligence and ability to establish strong and trusting relationships.
Excellent relationship building, communication and influence skills.
Strong written communication skills. Ability to distill and convey information in a compelling manner.

Tenure: The expectation is the Chief of Staff position is a ~24 month position, and you will graduate to a senior operating role at Gusto afterwards.

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.

Press: www.gusto.com/press including a broadcast interview Josh did
Gusto’s investors: www.gusto.com/investors
Customer spotlight: https://gusto.com/customers and public customer comments (from Twitter)
Company values: www.gusto.com/values -- these guide all aspects of how Gusto is run. The company has big ambitions, but being proud of how those goals are achieved matters just as much to the team.

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.

Entrepreneur: Q&A around Josh’s philosophy and learnings while building Gusto
Quora: Recent AMA Josh did on his life philosophy, leadership style, and Gusto’s market
Inc: How to Keep Your Culture as you Scale
NYTimes: Directing Without Dictating (from an interview Josh did)
WSJ: The Power of Entrepreneurial Ecosystems -- start-ups are not a zero sum game and we're here to help each other
Business Insider: How To Build A Team Of Owners, Not Employees