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Currently tracking 17 active AI roles, down 19% versus the prior 4 weeks. Primary focus: Agent · Engineering. Salary range $111k–$321k (avg $220k).

Hiring
17 / 20
Momentum (4w)
↓-5 -19%
21 opens last 4w · 26 prior 4w
Salary range · avg $220k
$111k–$321k
USD · disclosed roles only
Tracked since
Oct '25
last role 2w ago
Hiring velocityscroll left for older weeks
1 new role
Feb 24
1 new role
Mar 3
1 new role
24
1 new role
Apr 7
1 new role
May 12
1 new role
Jun 16
1 new role
Jul 7
1 new role
Aug 4
1 new role
Sep 15
1 new role
29
1 new role
Oct 6
2 new roles
20
2 new roles
Nov 17
3 new roles
Dec 8
1 new role
15
1 new role
29
4 new roles
Jan 5
1 new role
12
1 new role
19
1 new role
26
2 new roles
Feb 2
1 new role
9
4 new roles
23
5 new roles
Mar 2
3 new roles
9
1 new role
16
8 new roles
23
8 new roles
30
6 new roles
Apr 6
6 new roles
13
7 new roles
20
4 new roles
27
10 new roles
May 4
5 new roles
11
5 new roles
18
7 new roles
25
8 new roles
Jun 1
1 new role
8

Gusto currently has 25 active job listings related to artificial intelligence. The majority of these roles, 68%, are focused on agents, with application roles making up another 28%. Product and Engineering are the top hiring functions. The company is frequently seeking candidates with experience in agent orchestration, LLM observability, and guardrails.

Auto-generated from active job postings · last refreshed 2026-05-24

Frequently asked questions

  • What AI roles is Gusto hiring for?

    Gusto currently has 23 active AI-related roles in our index. The most common open titles are: Benefits Engineering Manager, Enterprise Application AI Architect, Head of Client Experience, Symmetry , Head of Customer Referral & Emerging Channels, Head of ML/AI Engineering. Most positions are in Product and Engineering.

  • What stage of AI development does Gusto focus on?

    Gusto's active AI hiring is concentrated in: agents (70%), application (30%). These categories follow a seven-stage AI lifecycle: data, pre-training, post-training, serving infrastructure, agents, evaluation, and application.

  • Where is Gusto hiring AI talent?

    Gusto is hiring AI talent in: United States (23 roles), Canada (3 roles).

  • What technologies does Gusto's AI team work with?

    Job postings at Gusto most frequently reference: agent orchestration, llm observability, guardrails, model serving, rag.

  • How many AI roles has Gusto posted recently?

    In the past 30 days, Gusto has posted 6 new AI-related roles. That is a -25% change versus the prior 30 days (8 → 6).

Jobs (18)

15 AI · 81 total active
FilteredCountryCanada×
Show
Active onlyAI only (≥ 7)
Stage
AllServe · 1Agent · 24Ship · 8
Function
AllProduct · 75Engineering · 43
Country
AllUnited States · 117Canada · 18
Sort
AI scoreRecentTitle
TitleStageFunctionLocationFirst seenAI score
Principal Product Designer, CoreX AI
Principal Product Designer to lead AI design across Gusto, defining AI's interaction model, UX principles, and product direction. This role is strategic and hands-on, shaping AI-powered workflows, ensuring user trust, and shipping customer-facing AI capabilities. The designer will work with senior leaders to define the AI portfolio and establish scalable AI interaction patterns.
ShipAgentProductToronto, ON +3 · RemoteMar 47
Enterprise Application AI Architect
This role focuses on integrating AI and automation into Gusto's enterprise applications, specifically designing and managing AI agents and Model Context Protocols (MCPs) to make internal systems smarter and more autonomous. The goal is to transform reactive workflows into predictive, self-improving platforms, ensuring security, compliance, and measurable impact within the IT and Enterprise Applications organization.
AgentEngineeringON +3 · RemoteNov '257
Senior Staff Service Designer
Senior Staff Service Designer role focused on designing and building AI-assisted service workflows within an enterprise AI context. The role involves creating coherent, resilient, and understandable interactions between AI systems, product experiences, and human teams, with a focus on improving customer experience and operational efficiency. This is a product-focused role that uses AI tools to prototype and improve service delivery.
AgentProductToronto, ON +3 · Remote6d ago5
Senior Pricing and Monetization Manager
This role is for a Senior Pricing and Monetization Manager at Gusto, a fintech company. The role focuses on developing and executing pricing and monetization strategies for Gusto's platform, including payroll, time management, HR, and financial services. While the company emphasizes an 'AI-native environment' and expects employees to use AI tools, the core responsibilities are product strategy, commercial go-to-market initiatives, and KPI management, rather than direct AI/ML model development. The role involves collaborating with various teams and shipping MVPs and pilots, indicating a focus on product delivery within an AI-enhanced workflow.
—ProductToronto, ON +2 · Remote4w ago5
Partner Manager
Gusto is seeking a Partner Manager to drive the strategy and growth of their Gusto Pro accounting firm partners. The role involves managing existing revenue, identifying growth opportunities, building relationships, and collaborating with internal teams to influence product roadmap. The ideal candidate will have 5+ years of experience in a sales-related function, a track record of exceeding sales quotas, deep understanding of the accounting firm landscape, and proven experience integrating AI into their daily workflow for sales, research, and summarization.
—ProductToronto, ON +2 · Remote7w ago5
Senior Paid Social Lead
This role is for a Senior Paid Social Marketing Lead who will own the paid social program end-to-end, from brand awareness through conversion, across various social channels. The role involves managing multi-million dollar budgets, defining measurement frameworks, leading creative strategy and testing, and acting as an internal subject matter expert on paid social and AI-powered marketing workflows. The ideal candidate will be AI-fluent in practice, using AI tools consistently in their daily workflow to accelerate tasks and implement AI-driven efficiencies.
—ProductToronto, ON +2 · Remote8w ago5
Head of PEO Sales
Gusto is seeking a founder-minded sales leader to establish and build their PEO sales organization from the ground up. This player-coach role involves designing the sales motion, building the team, carrying a personal book of business, and leveraging AI tools to drive sales performance and adoption. The ideal candidate has PEO sales expertise and experience building sales teams in a high-growth environment.
—ProductToronto, ON +1 · RemoteApr 85
Staff Product Designer, Retirement
Gusto is seeking a Staff Product Designer for their Retirement team. This role involves shaping strategy, aligning teams, and designing a high-trust retirement experience. The designer will lead the design process, focusing on improving setup, account management, and the connection between payroll and retirement. A key aspect of the role is leveraging AI in daily workflows for faster prototyping and learning, and identifying opportunities where AI can enhance the customer experience. The role also involves translating regulatory requirements into clear UI patterns and mentoring design peers.
—ProductToronto, ON +4 · RemoteApr 15
Principal Product Manager, Tax Platform
Product Manager for Gusto's Tax Platform, focusing on strategy, roadmap, and execution of core systems for tax calculation, tracking, payment, reconciliation, and filing. The role involves modernizing legacy systems, ensuring accuracy, scalability, and resilience in a regulated fintech domain, and partnering with various teams. Experience with AI-driven features is a plus.
—ProductToronto, ON +3 · RemoteJan 265
Staff Product Designer, Contractors
Gusto is seeking a Staff Product Designer to lead design strategy and execution for their contractor products. The role involves driving end-to-end design processes, partnering with cross-functional teams, and translating insights into user experiences. A key aspect of this role is the expectation for designers to be AI-fluent, actively using AI tools for prototyping, feedback loops, and improving user experiences, reflecting Gusto's AI-native design organization.
—ProductToronto, ON +3 · RemoteJan 85
Senior Data Engineer
Senior Data Engineer at Gusto responsible for building tools and systems that make Gusto's data consistent, user-friendly, and helpful. This role involves partnering with analytics, product, and engineering teams to deliver data solutions that drive business and customer impact, with a functional understanding of leveraging AI and automation in data engineering.
—EngineeringToronto, ON +3 · RemoteNov '255
Head of Product, Payroll
Gusto is seeking a Head of Product to lead their core Payroll product and business area. This role involves defining strategy, roadmap, and business performance, leading a product team, and collaborating with cross-functional departments to deliver an exceptional Payroll experience. The ideal candidate has extensive product management experience, particularly in SMB-focused software and regulated categories, with a strong track record of building and scaling mission-critical products.
—ProductToronto, ON +3 · RemoteOct '255
Head of Social and Influencer Marketing
The Head of Social and Influencer Marketing will define and lead Gusto's social and influencer strategy to grow brand awareness, engagement, and consideration among small businesses. This role involves building and managing a team, overseeing social channels, content strategy, and influencer programs. A key aspect is leading Gusto's AI-native evolution by defining standards for ethical and high-quality AI usage across social and brand channels, including developing AI-assisted workflows and ensuring compliance with AI policies. The role requires a proven track record of scaling social and influencer initiatives and operating at an advanced level of AI fluency for the function.
—ProductToronto, ON +2 · RemoteOct '255
Senior Staff Product Designer, Finance
Gusto is seeking a Senior Staff Product Designer for their Finance team. This role will set the UX vision and strategy for interconnected product areas including Business Money, Consumer Money, Payments, and Risk. The designer will focus on defining what AI-first financial UX looks like at scale, ensuring products are trustworthy and empowering for small businesses. The role involves influencing product strategy, driving high-impact design opportunities, and hands-on design work, while also developing other designers.
—ProductToronto, ON +3 · RemoteAug '255
Senior Software Engineer, Data Platform
Senior Software Engineer to architect, build, and maintain the data infrastructure at Gusto. Collaborate closely with Data Science, Business Intelligence, and analysts across Gusto teams to help them achieve their goals. This role is a software development position with knowledge of data architectures and data delivery.
—EngineeringToronto, ON +3 · RemoteApr 20
Staff Mobile Software Engineer, iOS
Gusto is seeking a Staff Mobile Software Engineer for their iOS team. The role involves architecting, building, testing, and refining the native iOS app and supporting mobile web views. Responsibilities include developing product features, collaborating with cross-functional teams, and scaling essential services like push notifications and localization. The ideal candidate will have at least 6 years of Swift/iOS experience, strong communication skills, and a self-driven mindset. While AI is fundamental to Gusto's operations and employees are expected to engage with AI tools, this specific role focuses on core mobile engineering rather than direct AI/ML model development.
—EngineeringToronto, ON +1 · RemoteFeb 240
Senior Editor & Motion Designer, Brand Studio
This role focuses on editing and motion design for brand storytelling, product narratives, and social content. The Senior Editor & Motion Designer will own the post-production process from rough cut to final delivery, shaping content through pacing, sound, animation, and color. A key aspect of the role involves building repeatable templates and workflows, and leveraging AI-enabled workflows to enhance efficiency and output quality. The position requires strong collaboration skills and a maker mindset, with a focus on both the creative output and the process improvement.
—EngineeringToronto, ON +3 · RemoteJan 150
Staff Mobile Software Engineer, Android
Staff Mobile Software Engineer, Android with 8+ years of experience to architect, build, test, and refine Gusto's native Android app, develop product features, collaborate with cross-functional teams, and scale essential services. The role emphasizes ownership of scaling shared services and keeping up with Android advancements, working closely with Product, Identity, Security, System Design, and Infrastructure teams.
—EngineeringToronto, ON +2 · RemoteMay '250