Hi Dr. Job! I’ve been reading about Gusto and I’m curious — can you tell me what it’s like to work there?
Ms.Smith
Gusto Company Overview: Mission, History & Leadership
First off, what exactly does Gusto do? I’ve seen the name but I’m not totally clear on their focus.
Ms.Smith
Sure. Gusto is a San Francisco-based company that focuses on Payroll and HR platform for SMBs. They were founded in 2011 and have been building their team in the Management & Operations space ever since. The company is led by Joshua Reeves. Right now the company has around 2000 people on staff.
Dr.Job
That’s interesting. How does their product actually work? What problem are they solving?
Ms.Smith
At its core, Gusto is working on Payroll and HR platform for SMBs. Think of it this way — the Management & Operations industry has real challenges that traditional approaches haven’t fully solved, and Gusto is trying to tackle those gaps. They’ve been able to attract serious funding, which suggests investors believe the approach has potential. Founded in 2011, the company has over 15 years of experience in the industry and a well-established track record.
Dr.Job
Who’s running the show? And what’s their background?
Ms.Smith
Joshua Reeves serves as CEO. Based on the company’s progress and funding track record, the leadership appears to have relevant industry experience. The team is based primarily in San Francisco, CA, and with approximately 2000 employees, the company has a deep management structure and well-defined departments.
Dr.Job
Founded
2011
Headquarters
San Francisco, CA
CEO
Joshua Reeves
Employees
~2000
Total Funding
$175M (Series E)
Key Investors
T. Rowe Price
Industry
Management & Operations
Gusto Funding: $175M Raised & Key Investors
I saw they’ve raised a lot of money. Can you break down the funding situation?
Ms.Smith
Gusto has raised $175 million to date, with the most recent round being a Series E. Their investor list includes T. Rowe Price. That’s a solid group of backers, and the funding level tells you that outside parties have done their due diligence and believe in what the company is building.
Dr.Job
As someone looking at jobs, should I care about the funding? What does it actually mean for employees?
Ms.Smith
It matters more than people think. A company with $175M in the bank isn’t scrambling to make payroll — it has runway to invest in its team, tools, and growth. For you as a potential employee, that usually means competitive compensation, better resources, and less risk of sudden layoffs. It also means they’re probably hiring, which gives you more leverage in negotiations. That said, funding alone doesn’t guarantee a great workplace, so always do your own research.
Dr.Job
Gusto Careers: Salary, Benefits & Work Culture
What kind of roles do they typically hire for? And is it mostly technical, or are there business-side positions too?
Ms.Smith
With a team of about 2000 people, Gusto is at the stage where they need a mix of both. You’d expect to see roles in engineering, product, and R&D given their focus on Payroll and HR platform for SMBs, but companies this size also hire for operations, marketing, sales, and general business functions. Check their careers page for current openings — the mix changes as priorities shift.
Dr.Job
What about day-to-day culture? Is it the typical startup grind, or something different?
Ms.Smith
At 2000 employees, you’re going to feel the startup energy — things move fast, roles can overlap, and you’ll likely wear multiple hats. The upside is that you’ll have real visibility and impact. Being in San Francisco puts them in a strong talent market, which usually means the team around you will be sharp. One thing to keep in mind: early-stage companies can be exciting, but the pace isn’t for everyone. I’d recommend reaching out to current employees on LinkedIn to get a candid take before applying.
Dr.Job
This is really helpful, Dr. Job. I’ll dig into their careers page and see what’s open. Thanks!
Ms.Smith
Company Information
Company: Gusto Industry: Management & Operations Headquarters: San Francisco, CA Founded: 2011 CEO: Joshua Reeves Source:https://gusto.com