Senior Manager of Agentic Strategy & Operations, Gusto
$133.5-204.3k
Salary varies depending on location. Plus RSUs
Automated payroll, benefits & HR platform
Open for applications
Automated payroll, benefits & HR platform
1001+ employees
Open for applications
$133.5-204.3k
Salary varies depending on location. Plus RSUs
1001+ employees
Company mission
To grow the small business economy.
Role
Who you are
- 8+ years in operations, product, or AI roles — with at least 2 years designing and deploying AI-assisted or agentic workflows
- Strong fluency with LLM systems, including prompt design, evaluation, and production behavior at scale
- Hands-on experience with agentic tooling, orchestration frameworks, or MCP-style integrations — conceptual familiarity is not sufficient at this level
- Experience designing human-in-the-loop (HITL) systems with clear escalation logic, override controls, and compliance-aware checkpoints
- Working knowledge of multi-agent systems and tool coordination
- Strong operational judgment: able to define and diagnose workflow metrics
- Proven track record influencing cross-functional stakeholders — including Product, Engineering, Legal, Security, and Compliance — in writing, in design reviews, and in high-stakes forums
- Familiarity with Responsible AI practices, governance, and risk management in production environments
- Proven ability to operate in high ambiguity, create clarity, and drive alignment across technical and non-technical audiences
- Strong systems thinking with a bias toward execution and measurable outcomes
- Deep empathy for small business customers and the employees who serve them
What the job involves
- We are building AI-powered, agentic workflows to transform how service operations scale, resolve customer needs, and maintain quality in high-stakes environments. At Gusto, that means designing systems that can earn the trust of small business owners — where a wrong answer or a missed escalation has real consequences
- As an AI Solutions Architect, you will own the end-to-end design and performance of these workflows in production — where models, tools, data, and human judgment come together to deliver outcomes. This is not a traditional architecture role
- You will design, prototype, deploy, and continuously improve AI-driven systems that directly impact customer experience and operational efficiency. You will also play a key role in shaping the evolution of our AI platform by identifying capability gaps, prototyping solutions, and informing the primitives required to scale agentic systems effectively
- You will report into the Service Transformation org and work at the intersection of AI governance, service quality, and operational transformation — operating as the connective tissue between Engineering, CX, Legal, and Compliance as Gus, Gusto's AI assistant, scales
- The mission of our Service Transformation (CXT) team is to quickly evolve and scale how Gusto delivers outstanding service experiences and leverages AI to do so. Our team designs the systems, governance frameworks, and feedback loops that allow Gusto's service model to improve continuously, operate reliably, and earn the trust of the customers and employees who depend on it
- Architect, prototype, and own end-to-end agentic service workflow frameworks, from scoping through production deployment and iteration — including solve and assist targets, HITL protocols, override logic, and downstream quality safeguards
- Analyze SOPs, operational metrics and interaction data to identify and prioritize high-impact automation opportunities based on volume, risk, and customer impact
- Design and implement multi-agent orchestration patterns across tools, data sources, and decision steps within a single end-to-end workflow
- Apply and influence AI platform capabilities in partnership with CoreX (Gusto's AI Platform team) — including orchestration, retrieval, and evaluation — helping define what needs to be built to support production workflows at scale
- Identify platform gaps, prototype workflow-level solutions, and partner with engineering to shape the primitives required for reliable, scalable AI systems
- Serve as the primary CX voice in Legal, Security, Compliance, and CoreX forums — translating CX quality stakes and workflow risk into terms each audience acts on, and ensuring governance requirements are embedded in design, not retrofitted after launch
- Strengthen evaluation frameworks and feedback loops to ensure quality, compliance, and continuous improvement; contribute to Gusto's human evaluation programs and AI governance practices through deep partnership with our internal CX Labs team
- Partner with Data teams to define and track workflow performance — including solve and assist rate, AHT, rework rate, and customer effort score — clearly distinguishing between model-level, workflow-level, and operational drivers
- Build ROI models to quantify workflow impact across efficiency, quality, and cost before and after deployment
- Represent workflow performance and risk to senior stakeholders with appropriate precision and brevity; communicate in a way that drives action, not overwhelm
- Lead through ambiguity and rapid change: the function is still being defined, and you will help define it
Our take
For many small businesses, vital administrative tasks such as payroll, taxes, and benefits are manual tasks that take time and energy - which many SMB owners don’t have. The co-founders of Gusto all come from small business backgrounds, which is why they created a platform that would handle employee payments, benefits administration, and compliance support specifically for small businesses.
The company may have started slowly, as the founders focused on nailing each individual aspect of Gusto’s operations, but has now skyrocketed to unicorn status with more than 400,000 customers and a multi-billion dollar valuation. And in 2021, Gusto began acquiring other companies to strengthen its offering and position in a competitive market, including the likes of Ardius, Symmetry and Guideline.
Through its continued acquisitions and fundraising efforts, the company has carved out a strong position for itself in the space. It continues to expand its platform, for example by partnering with Parafin to launch a payroll line of credit for small businesses, and more recently launching Cofounder, an AI teammate tailored to the needs of small businesses.
Steph
Company Specialist at Welcome to the Jungle
Insights
45% employee growth in 12 months
Company
Funding (last 2 of 9 rounds)
May 2022
$55m
SERIES E
Aug 2021
$175m
SERIES E
Total funding: $706.3m
Company benefits
- Medical, dental, and vision insurance for employees and dependents
- Family care and support, including family planning and fertility benefits
- Gender-affirming care and support
- A variety of mental health resources
- Paid vacation, sick time, bereavement, and holidays, paid leaves, sabbatical, and more
- Free meals and refreshments at the office (conversation and community is an added bonus!)
Company HQ
Central Waterfront, San Francisco, CA
Leadership
Joshua Reeves
(CEO & Co-Founder)Studied Electrical Engineering at Stanford and went onto co-found Gusto in 2011.
Tomer London
(CPO & Co-Founder)Has a PhD in Electrical Engineering from Stanford. Was a Researcher at Intel, and then interned at Bump Technologies. Co-founded Vizmo before co-founding Gusto in 2011.
Edward Kim
(Head of Technology & Co-Founder)Studied Electrical Engineering at Stanford. Was Senior Project Engineer at Volkswagen of America Electronics Research Lab and then co-founded Picwing before co-founding Gusto in 2011.
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