G

Gusto

Runs payroll and HR software for small businesses

Head of Risk and Money Services

Full-TimeUpdated on 10/10/2026
$170k - $250k/yr+ Equity (RSUs)
Expert
San Francisco, CA, USA+2 moreMore locations: New York, NY, USA | Denver, CO, USA
HybridEmployees in these locations are expected in the office approximately 2–3 days per week.
Finance & BankingRisk Management

About the job

Requirements
  • At least 12 years of industry experience leading financial services operations in banking, payments, money movement, fraud and risk, or related regulated domains, with demonstrated depth in how money moves, where it fails, and how regulated institutions respond.
  • At least 7 years as a departmental leader running large, multidisciplinary financial services operations teams, including managing through senior direct reports across distinct operational functions.
  • Deep expertise in banking and money movement operations, including Reg E dispute processing, BSA/AML operational response, ACH and real-time payments risk, sponsor bank operational requirements, and controls infrastructure that makes regulated money movement auditable.
  • Hands-on background in fraud and payment risk, including building or leading fraud operations that make real-time decisions with material financial consequences, payment risk scoring, account takeover response, and fund recovery operations.
  • Experience in consumer financial products such as consumer banking, digital wallets, or cash advances, including required SOPs, customer communications frameworks, and compliance controls.
  • Track record of standing up or formalizing regulated financial functions by building SLAs, controls documentation, governance, and reporting infrastructure that makes regulated work auditable, scalable, and defensible under examination.
  • Experience navigating sponsor bank and regulatory relationships, including bank partnership constraints, audit readiness, operational policy alignment, and escalation to compliance and legal.
  • Track record of leading high-stakes, real-time financial decisions where individual decisions carry material financial cost to customers or the business.
  • Experience building reliable, scalable, AI-native operations in regulated domains, with judgment about where automation can accelerate work and where regulatory accountability remains essential.
  • Experience working cross-functionally with Product, Engineering, Compliance, Legal, and Risk, particularly in fintech, banking, or financial product environments where operational leaders drive product decisions.
  • Track record of delivering for multiple senior partners across overlapping financial product lines.
  • Demonstrated ability to lead through significant organizational change with clarity, candor, and consistency during periods of high operational flux.
  • Demonstrated ability to build diverse and inclusive teams.
Responsibilities
  • Own Risk & Money Services end to end, including fraud and payment risk decisioning, BSA/AML compliance, Reg E dispute operations, collections, and the operational backbone of Gusto’s money products; own customer experience, regulatory posture, and financial outcomes across the function.
  • Lead a multidisciplinary regulated financial services organization through leaders who own their functions; develop, hire, and scale those leaders while maintaining quality, speed, and regulatory integrity across the practices.
  • Establish Risk & Money Services as a defined operational function by setting governance, metrics, SLAs, reporting infrastructure, controls documentation, audit readiness, workforce management, and escalation frameworks.
  • Be accountable for high-stakes real-time decisions on payroll release, provisional credit for disputes, fraud signals, and timely fund recovery.
  • Lead the operational program governing Reg E dispute obligations, including intake, investigation, provisional credit, resolution, and customer communication, in partnership with Compliance and Legal; ensure practices are auditable, scalable, and defensible.
  • Own customer-facing operational work triggered by BSA/AML alerts, including transaction monitoring response, customer outreach, and account action, in partnership with Compliance; ensure timely and documented responses that meet sponsor bank and regulatory obligations.
  • Build the operational infrastructure for Gusto Wallet, Cash Advance, and the consumer financial product suite, including SOPs, workforce models, controls, and SLAs.
  • Partner with the shared service platform and AI organization to introduce AI agents, semantic knowledge, and automation into Risk & Money Services while maintaining regulatory accountability.
  • Serve as the operational owner across money and risk product organizations, translating operational and regulatory realities into product priorities and product roadmaps into operational and regulatory readiness.
  • Represent Risk & Money Services directly with sponsor bank partners, regulators, and auditors on risk and money movement matters.
  • Establish the operational playbook for new financial products, including business banking expansion, new money services, and future consumer financial products, with controls and operational readiness in place.
  • Support team members’ development and help them achieve their professional goals.

About the company

Gusto runs payroll, benefits administration, and HR software for small and midsize businesses that want to manage their teams in one place. Its payroll system calculates wages and taxes, files required forms, and connects employee hours with pay runs. Employers use the same platform to enroll workers in health insurance and retirement plans, manage time off, and organize hiring paperwork, while staff access paystubs through personal accounts. Businesses pay monthly subscription fees based on their plan and workforce size, with extra charges for selected services and faster payment options. Gusto was founded in 2011 and is headquartered in San Francisco, California.

Company Size

1,001-5,000

Company Stage

Series E

Total Funding

$706.2M

Headquarters

San Francisco, California

Founded

2011

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Simplify Jobs

Simplify's Take

What believers are saying

  • Gusto has broad customer reach: it reports serving more than 500,000 businesses nationwide.
  • Staff get time to recharge: Gusto's careers page lists sabbaticals alongside paid vacation and other leave.
  • Accountants have a reason to refer clients: Gusto's partner tiers share up to 20% of revenue.

What critics are saying

  • Revenue has limited contract protection: Gusto's core payroll plans run month to month and allow cancellation anytime.
  • Hub-based Gusto staff face office requirements: job postings specify roughly two to three days weekly, sometimes more.
  • Gusto's banking product relies on partners: nbkc bank supplies Wallet's spending accounts and banking services.

What makes Gusto unique

  • Gusto powers other software brands: Embedded runs payroll inside partners' apps while partners control the interface.
  • Switching from incumbents is easier: Gusto Pro imports employee details from ADP Run and QuickBooks payroll files.
  • Gusto connects paychecks to spending: Wallet debit cards are limited to employees paid through its payroll.

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Benefits

It's a marathon, not a sprint: Employees celebrating 5 or 10 years at Gusto enjoy a month-long sabbatical to travel and relax after all their hard work.

Meals and conversations: Free meals, snacks, and drinks to keep us fueled, but more importantly: they bring people together and foster community.

Wellness for every body: We're proud to offer inclusive health care such as hormone treatments, gender-affirming surgery, therapy, family planning, and more.

The time you need: Our flexible PTO policy means every employee is encouraged to take the time they need now to keep doing great work, long term.

Family-friendly benefits: Fertility treatments, primary and secondary parental leave, sleep coaching, house cleaning for new parents, and more.

Be well, be you: Get free, comprehensive medical, dental, and vision benefits, plus a monthly fitness stipend and mental health resources too.

Growth & Insights and Company News

Headcount

6 month growth

-5%

1 year growth

-3%

2 year growth

-4%
Small Business Trends
Oct 10th, 2026
Gusto enhances Claude connector to simplify Small Business management.

Gusto enhances Claude connector to simplify Small Business management. In an era where efficiency is paramount, Gusto has unveiled its enhanced connector for Claude, which aims to simplify payroll management for small business owners. This innovation is not just a step forward in streamlining administrative tasks; it's a leap toward integrating artificial intelligence into daily operations for those juggling multiple responsibilities. By leveraging AI tools, small business owners can now spend less time on routine administrative work and more on strategic initiatives that drive growth. The Gusto connector for Claude empowers small business owners to manage essential functions directly through conversational commands. Gusto's recent survey indicates a growing trend, with 44% of new businesses now incorporating AI into their daily operations - an increase from 21% just a year before. This shift demonstrates that small business owners are transitioning from experimentation to strategic integration of AI into their operations. With the upgraded connector, owners can easily manage payroll, timesheets, and personnel details all within a single conversation. By bringing context and actionable insights together, the connector enhances the ability of AI to understand the real state of a business and prepare the next steps based on specific needs. Discover more Business Operations Software Management Training Courses Small Business Trends For instance, small business owners can simply instruct the AI to perform tasks such as adding bonuses to payroll, updating employee hours, or pulling labor costs for budget sheets - all through natural language commands. Small business owner Alex Aukerman of Ox Asphalt shared his experience: "I use the Gusto connector for Claude to make more data-driven decisions for a small business like ours. By pulling timesheet data into Claude, I can see which crew was on which job and how long each job took, then feed that information back in to improve future scheduling. As a result, we're more efficient, our employees are happier and less overworked, and we feel far more confident making decisions based on real data instead of gut feeling." The Gusto connector not only automates and simplifies processes, but it also keeps business owners in control. All actions prepared by Claude, including hours, bonuses, deductions, and paid time off, require final approval from the owner before they are executed. This level of oversight ensures that business owners can maintain accountability while benefiting from improved efficiency. Looking beyond payroll, Gusto plans to expand the connector's capabilities to include full support for company setup, onboarding of employees and contractors, pay schedule configuration, and enhanced benefits visibility. These features signify Gusto's commitment to equipping small businesses with tools that can adapt to their evolving needs. However, while the benefits are evident, small business owners should consider potential challenges in adopting AI tools like the Gusto connector. For instance, while AI can streamline administrative tasks, it also requires a degree of user comfort and familiarity with conversational interfaces. Furthermore, data integrity and security will always be of paramount importance, and business owners must ensure that their data remains protected while using these innovative solutions. Discover more Open Biz Account Read Market News Small Businesses Despite these challenges, the potential for increased efficiency and profitability through the use of AI is substantial. As AI becomes an integral part of business management, the ability to harness its benefits can lead to improved employee satisfaction, better decision-making, and ultimately, business growth. In the fast-paced world of small business, tools like the Gusto connector for Claude are paving the way for more strategic management approaches. As owners embrace these advancements, they stand to gain a competitive edge by transforming how they operate - one conversation at a time. For more information about the Gusto connector for Claude, check out the official announcement at Gusto's press release here. Image via Google Gemini

PR Newswire
Oct 7th, 2026
Gusto unveils redesigned Pro platform with AI workflows and multi-client Model Context Protocol for accountants

Gusto announced major updates to its platform for accounting firms at its Gusto Next event. The company unveiled a redesigned Gusto Pro with AI-assisted workflows that automate payroll tasks, including extracting hours from emails and generating reports automatically. The platform now features Pro Gus, an AI assistant built for accountants. Gusto also launched a multi-client Model Context Protocol, allowing accountants to connect Gusto once and work across all clients from a single interface within their existing AI tools. Previously, accountants had to connect and disconnect for each client individually. The company expanded its Partner Program with Marketing Development Funds, Partner Development Funds, and AI agents to help firms acquire clients and grow advisory services. Starting mid-November 2026, revenue sharing will extend to 401(k) plans. Gusto serves over 500,000 small businesses and more than 23,000 accounting firms.

Under30CEO
Oct 6th, 2026
Business Compliance gets automated in Gusto's new service.

Business Compliance gets automated in Gusto's new service. Gusto announced general availability of Gusto Business Compliance on October 1, 2026. The service takes care of registering with state tax agencies, filing yearly reports, and similar paperwork for companies that hire employees in more than one state. It arrives about six months after Gusto bought the compliance automation company Mosey. If you have ever hired a remote teammate in a new state, you know the dread. One hire can quietly create a registration duty you did not plan for, and missed deadlines get expensive. Let's walk through how to think about business compliance as your team spreads out, and what this launch changes. What Gusto Business Compliance covers. Gusto serves more than 500,000 small businesses, and the new service is open to all of them. Rather than a checklist you manage yourself, it takes over a bundle of recurring chores. How the compliance service is organized | Job to be done | What the service handles | | Getting set up in a new state | State tax registration, foreign qualification, registered agent service | | Staying current | Annual report filings and proactive alerts | | Catching surprises | Monitoring of government mail | | Getting help from a person | A dedicated Compliance Concierge Team | Gusto also introduced HR Partners, which connects eligible customers with experienced HR specialists. A Gusto PEO, which would bundle pay runs, benefits, people operations, and legal upkeep, is expected in the coming months. Why this problem is bigger than it looks. The company's own research says roughly 50 percent of owners feel compliance eats too much of their time. Roughly three in four name tax filing as the most time-consuming piece. Those figures come from the company's announcement, so treat them as a signal rather than a census. Still, the pain is real. Compliance rarely feels urgent until a notice arrives, and by then penalties may already be running. Because founders wear many hats, this work often lands on whoever has the most spare minutes, which usually means nobody. Where multi-state hiring creates hidden duties. Hiring across state lines is now normal for young companies. A contractor becomes an employee, a sales rep moves to another city, or a great engineer lives somewhere you have never operated. Each of those moves can trigger new tax accounts and filings. That is one reason the business filing wave matters. More new companies means more first-time owners meeting these rules for the first time. Meanwhile, state agencies do not slow down for beginners. How to decide whether to automate. Automation is not automatically the right call. Use a few simple tests before you buy anything. * Count the states where you have employees today and where you plan to hire in the next year. * Estimate the hours per month someone spends on filings, then price that time honestly. * Ask what happens if a deadline slips and who pays the penalty. If you have employees in just one state, a good accountant may be enough. If you are adding states quickly, software that watches deadlines for you starts to look like insurance. Protect cash while you add compliance help. Every new vendor changes your monthly burn. Therefore, compare the fee against the cost of a single missed filing, and fold it into your regular cash flow management review. Pricing was not detailed in the announcement, so ask for a written quote before you commit. It also helps to read the government's own basics. The SBA's guidance on hiring employees outlines the federal and state steps every employer should know, which gives you a baseline to judge any vendor against. Do not forget the people side. Compliance is not only taxes. Benefits, leave rules, and workplace policies vary by state as well. For example, a growing team may also need a plan for small business health insurance as it crosses headcount thresholds. The HR Partners offer is aimed at exactly this gap. Founders without an HR leader can get expert answers without a full-time hire, though availability is limited to eligible customers for now. What to watch from here. The PEO is the next piece to track. A PEO changes who is the employer of record for certain purposes, so read the contract terms carefully when it launches. Compare it with your current setup on price, control, and exit terms. For now, the practical move is simple. List your states, check your registrations, and put every annual deadline on one shared calendar. Whether you automate or not, a clear map of your obligations is the cheapest protection a growing company can buy. Finally, assign ownership. Compliance fails when everyone assumes someone else is watching the calendar. Name one person, even part time, who confirms each filing is done and keeps proof on file. In addition, schedule a quarterly review so new hires and new states get added to the list before a deadline sneaks up on you.

PR Newswire
Oct 1st, 2026
Gusto launches automated compliance solution to ease multi-state hiring burden for 500K small businesses

Gusto has launched Business Compliance, a solution that automatically handles state and local compliance obligations for small businesses, particularly when hiring employees across state lines. The service registers businesses with state agencies, files annual reports, monitors government mail, and provides proactive compliance alerts. The launch follows Gusto's acquisition of compliance automation company Mosey less than six months ago. According to a recent survey, half of small business owners say compliance negatively impacts their growth, with three in four citing tax filing as their most time-consuming compliance task. Business Compliance is now available to all Gusto customers. The company also announced Gusto HR Partners, which provides access to senior HR leaders, available to eligible customers today. Gusto PEO, offering comprehensive payroll and benefits support, will launch in coming months.

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