Sales Onboarding Advocate

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About Gusto

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve.


All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about ourTotal Rewards philosophy.


AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process.

About the Role:

This role blends technical problem-solving with sales and customer service. After training, you'll be helping small business owners get their payroll and HR set up correctly. This means entering their past information, catching mistakes in their setup before they cause problems, and helping them navigate state and federal tax guidelines (every state does this differently, so you'll become the expert who can guide customers through all 50).

This team is where technical sales careers start at Gusto. You'll build a strong foundational understanding of payroll, tax, and compliance expertise while developing consultative sales skills, and that opens doors. Reps who excel here can grow into specialized roles working in Implementations and Solutions Engineering. If you're looking for a sales career with a technical backbone, this is where that path starts.

Here’s what you’ll do day-to-day:

  • Customer conversations: Handle high-volume customer interactions across phone and email with small business owners guiding them from onboarding to running their first payroll.
  • Pipeline management: Own your ticket queue the way a seller owns their opportunity pipeline.
  • Grow revenue: Proactively position plan upgrades and surface cross-sell opportunities for Health Insurance, Workers' Comp, and 401(k).
  • Technical diagnosis: Catch tax discrepancies live, troubleshoot unfamiliar state portals in real time, and make the right compliance call for each state, size, and industry combination.
  • Compliance setup: Configure sick time, PTO, and overtime policies to keep companies compliant from day one
  • Work across teams: You'll know when a customer's situation is something you can solve yourself versus when it needs a specialist, and you'll get that handoff started. You'll also work closely with our Risk team, asking customers for extra information when needed to build trust.
  • AI-powered workflows: Use assigned AI tools daily as a core part of how you work, surfacing friction and inefficiencies and giving feedback that shapes what gets built next.

Here’s what we're looking for:

  • Experience: 1+ years in a high-volume sales or customer service role where you were cross-selling, upselling, or hitting a quota/KPIs. We love to hire new grads too, so if that’s you, please be prepared to translate how your internship or prior work experience would translate to this type of role.
  • Eager to learn: You're excited to dive into a brand new industry and figure out the details, whether that's tax codes, compliance rules, or how payroll actually works behind the scenes.
  • Customer obsessed: You put customer needs first, listening closely to understand what they would benefit from and help them understand how different parts of our product will affect their business. You build trust through consultative conversations, and that trust is what drives the right outcome for both the customer and the business.
  • Drive: Goal-oriented and competitive in the best way, you want to hit your numbers and keep leveling up your sales game.
  • Communication: Strong across phone, email, and chat, with the flexibility to adjust your tone to the moment.
  • Adaptability: You're a problem solver who thrives on challenge and adjusting quickly when a situation shifts.
  • AI: Proven, day-to-day experience integrating AI into how you work, across writing, research, prep, and summarization, with a track record of giving clear, useful feedback that helps improve your tools and processes.

Our cash compensation amount for this role is $23.00/hr to $24.50/hr in Denver, Phoenix & Atlanta. 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. This includes non-office days for hybrid employees.


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. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you.

Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer.

Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...