Strategic Operations Lead, Gusto
$98.7-116k
Automated payroll, benefits & HR platform
Open for applications
Automated payroll, benefits & HR platform
1001+ employees
Open for applications
$98.7-116k
1001+ employees
Company mission
To grow the small business economy.
Role
Who you are
- Proven ownership: You’ve owned outcomes across complex, cross-functional work and consistently delivered results end-to-end
- AI-native builder (core requirement): You don’t just use AI tools. You build with them. You’ve designed and deployed AI agents, automations, or workflows that execute multi-step work, and you’ve measured the leverage created. This is required for success in this role
- Systems thinker: You identify root causes at the process level and build solutions that scale. You improve how teams operate, not just your own output
- Strong data fluency: You can structure problems, define success metrics, and turn data into clear, decision-driving narratives
- Operator + coach: You raise the quality of work around you through direct feedback, clear standards, and accountability
- Cross-functional leader: You’ve led initiatives across product, engineering, and operations and can drive alignment without direct authority
- Comfort with ambiguity: You create structure where none exists and move work forward without perfect information
- 4+ years in operations, program management, or business operations in a SaaS, technology, or operationally complex environment
What the job involves
- We’re hiring a Strategic Operations Lead, internally named Labs Lead, to build and run Benefits Labs, the system that governs how Gusto’s Benefits organization tests, validates, and scales operational change
- You will own the full Labs lifecycle, including intake, pilot design, execution governance, measurement, and recommendations to leadership. This is not a traditional program or operations role. Your responsibility is to build and operate the system that runs Labs
- This role is AI-native. You will design and run the agents, automations, and workflows that power how work is triaged, how pilots are executed, and how evidence is generated and synthesized. The goal is to create a system that can run many pilots in parallel with high quality and minimal manual intervention
- Your impact is measured by leverage: how much work the system can handle without you, how quickly the organization can test and scale changes, and how clearly leadership can make decisions based on evidence
- Benefits Labs sits within Benefits Business Operations today. You will be the founding operator, reporting to the Head of Benefits Business Operations, and will directly shape how this function evolves, including its future scope, structure, and investment
- Benefits Business Operations is responsible for how Gusto’s Benefits business improves and scales. The team operates across three domains: Automation, Carrier, and Quality, each focused on improving different parts of the operational system
- Labs sits across these domains as the governance layer for operational change. It ensures ideas are tested rigorously, measured consistently, and scaled intentionally
- Labs partners closely with org leadership, product, engineering, and transformation teams to turn strategy into execution and build systems that improve how the business operates
- You will operate and continuously improve the system that governs operational change across Benefits
- Own intake and triage: Run the AI-powered intake system that classifies, routes, and prepares incoming work. Determine the right path for each request and improve the system over time
- Run pilot governance: Ensure every pilot follows a clear structure with defined success metrics, checkpoints, and outputs. Use AI-driven workflows to manage execution and produce recommendations to scale, iterate, or stop
- Raise design quality: Pressure-test hypotheses, refine success criteria, and hold Pilot Leads accountable to standards. Improve the quality of work across the system without taking ownership away from teams
- Build and improve the system: Extend the existing agent and automation architecture across the Labs lifecycle, including intake routing, workflow execution, evidence synthesis, and readout generation. Increase speed, scope, and reliability over time
- Solve systemic problems: Identify inefficiencies in how operational change moves through the organization and convert repeatable problems into scalable, AI-powered workflows
- Drive decision-making: Develop analytical approaches and produce clear, evidence-based narratives that align stakeholders across product and CX and influence leadership decisions
- Lead cross-functional work: Own coordination across product, engineering, operations, enablement, and business partners. Manage complexity, align stakeholders, and deliver measurable outcomes
- Create clarity in ambiguity: Lead discussions on complex operational and product topics, helping teams converge on decisions and next steps
- Produce leadership-ready outputs: Deliver structured readouts, post-mortems, and recommendations using AI to generate and validate evidence efficiently
- Shape the future of Labs: Use what you build and learn to inform the long-term operating model, team structure, and investment strategy for Benefits Labs
- Raise the bar for others: Coach Pilot Leads and BizOps partners on AI-powered ways of working and hold a high standard for execution quality
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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