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Currently tracking 14 active AI roles, up 18% versus the prior 4 weeks. Primary focus: Agent · Product. Salary range $111k–$321k (avg $220k).

Hiring
14 / 16
Momentum (4w)
↑+4 +18%
26 opens last 4w · 22 prior 4w
Salary range · avg $220k
$111k–$321k
USD · disclosed roles only
Tracked since
Oct '25
last role yesterday
Hiring velocityscroll left for older weeks
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
Sep 15
1 new role
29
1 new role
Oct 6
2 new roles
20
2 new roles
Nov 17
2 new roles
Dec 8
1 new role
15
1 new role
29
4 new roles
Jan 5
1 new role
19
1 new role
26
2 new roles
Feb 2
4 new roles
23
5 new roles
Mar 2
2 new roles
9
1 new role
16
7 new roles
23
8 new roles
30
6 new roles
Apr 6
6 new roles
13
6 new roles
20
4 new roles
27
10 new roles
May 4
Gusto

Gusto

Fintech · Payroll

HQ
San Francisco, US
Founded
2011
Website
gusto.com

Jobs (10)

14 AI · 75 total active
FilteredFunctionProduct×CountryCanada×Clear all
Show
Active onlyAI only (≥ 7)
Stage
AllServe · 1Agent · 15Ship · 6
Function
AllProduct · 51Engineering · 24
Country
AllUnited States · 75Canada · 15
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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
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.
—
Product
Toronto, ON +2 · Remote
5d ago
5
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 · Remote3w 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 · Remote4w 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 · Remote5w ago5
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 · Remote6w ago5
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
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