GTM Insights & Operations, Gusto
$158.3-195.2k
2-3 days a week in office
Automated payroll, benefits & HR platform
Be an early applicant
Automated payroll, benefits & HR platform
1001+ employees
Be an early applicant
$158.3-195.2k
2-3 days a week in office
1001+ employees
Company mission
To grow the small business economy.
Role
Who you are
- 5+ years of experience in business operations, revenue/GTM operations, consulting, program management, or product management, ideally in high-growth technology companies
- Craft depth in one or more go-to-market disciplines. We're looking for meaningful experience across some of the following: sales, marketing, partnerships, or pricing & packaging as a craft—and if not those, deep experience in revenue analytics or finance as a craft
- Strong program management skills → end-to-end ownership of complex, cross-functional initiatives
- Operational excellence → proven ability to run team rituals and operating mechanics, including roadmaps, metrics/OKRs, forecasting, and business reviews
- Analytical rigor → comfortable working with data to surface insight, size opportunities, and inform senior decisions
- Excellent communication and collaboration skills → builds strong cross-functional relationships across sales, marketing, partnerships, product, finance, and operations
- Ownership mindset → proactive, comfortable flexing into ambiguous problems at any altitude
- Change leadership → able to guide teams through change with clear communication
- AI-Native Mindset → naturally seeks out ways to integrate AI into workflows to accelerate documentation, build smarter systems, and improve decisions
- Alignment with Gusto's values → customer empathy, grit, and a passion for helping small businesses thrive
What the job involves
- Gusto's GTM team drives revenue across Indirect and Direct Sales, Channel Partnerships, and Expansion Sales — and this role is the connective tissue that makes it all work. As a GTM I&O Lead, you'll own the operating infrastructure, planning rhythms, and cross-functional programs that keep GTM moving at speed
- This isn't a traditional ops role. You'll be embedded in the strategy — identifying where growth is won or lost, building the programs that unlock it, and designing the systems (including AI-augmented ones) that scale our capacity. You'll work directly with GTM leaders, Finance, Marketing, RevOps, and Product to translate ambition into execution
- You'll own a set of routes-to-market end to end, which means accountability for outcomes — not just coordination. This role blends strategic program management, operations, and business strategy
- You will join Gusto's Insights & Operations (I&O) team, and collaborate with a community of I&O peers across the business. I&O partners are trusted operators who bring urgency, clarity, and execution discipline to Gusto's most important initiatives—driving both strategy and execution, not one or the other
- Own the operating rhythm for your routes to market—roadmaps, OKRs/targets, planning, and business reviews (e.g., weekly forecast reviews, QBRs, steercos)
- Launch and manage cross-functional programs end to end, bringing urgency and clarity to initiatives that are ambiguous, at risk, or stalled
- Lead fiscal-year planning —translating strategy into concrete goals, owners, and timelines
- Own performance-lever workstreams: identify where growth is won or lost, structure the analysis, and drive cross-functional action
- Pilot AI-augmented approaches to program management and ops, and design re-usable automation patterns and AI agents that scale capacity across I&O and other Gusto teams
- Partner on Gusto-wide efforts and other high-impact cross-functional programs
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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