R&D Insights and Operations, Gusto
Growth
$221.3-298.7k
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
$221.3-298.7k
2-3 days a week in office
1001+ employees
Company mission
To grow the small business economy.
Role
Who you are
- 15+ years in operations, business operations, or strategy & ops at a high-growth technology company. This must include time spent building a growth function from an earlier, less mature stage
- Direct experience with the discipline behind growth decision-making: attribution and LTV modeling, testing and experimentation, and translating marketing/growth spend into demonstrable business impact
- A track record of working at the intersection of growth and go-to-market (or product and sales) — connecting teams with different incentives around a shared goal
- A strong point of view on how operations should scale: knowing when a problem needs a dedicated system vs. when it needs reprioritization, and resisting the urge to grow headcount by default
- Comfort starting as an individual contributor — going deep on one problem set before taking on broader scope — balanced with a demonstrated ability to build and lead teams when the moment calls for it
- Exceptional organizational skills, able to manage multiple senior stakeholders and competing priorities in a fast-moving environment
- Excellent written and verbal communication — able to tailor for executive audiences and drive alignment on hard, ambiguous trade-offs
- Financial acumen: comfortable managing financial tracking and reporting across a complex org
- Low ego and a bias toward collaboration: someone who works well across teams that all want the same outcome but don't yet have the bridges to get there together
- Deep empathy and enthusiasm for small business customers, and excitement about joining a company still very much in its building phase
- You're drawn to ambiguity, not intimidated by it — you'd rather build the map than wait for someone to hand you one
- You have a point of view and you share it — you'd rather say the harder, more useful thing than stay neutral to keep the peace
- You're energized by change and by building something new, even when it means occasionally undoing your own work to get it right
- You default to using AI to move faster and think bigger, and you save your own time and judgment for the calls only a person can make
What the job involves
- We're looking for a builder to help construct a world class Growth organization
- This is an opinionated leader that is motivated by creating big picture vision and digging into where the biggest opportunities are, sizing them, and building the systems, rigor, and connective tissue that let Growth and GTM operate cohesively
- This is a member of Gusto's Insights & Operations (I&O) team — our internal Strategy/BizOps function — embedded against Growth, partnering closely with our Head of Growth and our CRO-side GTM leadership
- This role is intentionally IC-first
- You'll start by going deep on the highest-leverage problems in Growth, build a point of view grounded in data, and drive it to outcome
- As trust and scope grow, this role is expected to expand — most likely into owning the operating bridge between Growth and our broader go-to-market organization, and potentially into building and leading a small team
- Gusto's Growth organization is on an ambitious trajectory: we're building toward a much more self-serve-led motion, and the opportunity ahead is significant
- As Growth scales, we have a chance to be much more intentional about how it connects to Product and to our go-to-market teams (sales, demand gen, expansion sales, pricing, etc) — building a shared, prioritized roadmap and clear visibility into dependencies from the ground up, rather than retrofitting it later
- Identify and size the highest-leverage opportunities for Growth: go from a fuzzy problem to a clear-eyed analysis of the opportunity, a recommendation on whether to pursue it, and a plan if the answer is yes
- Anchor on problems, not headcount: dig into what's actually slowing the Growth organization down, define how to build a best in class engine, size the opportunity, and decide what's worth solving before proposing who or what is needed — not the reverse
- Build the operating rhythm for Growth and drive execution against it: planning cycles, prioritization, and a shared, prioritized roadmap that makes trade-offs and dependencies visible across Growth R&D, Product R&D, and GTM
- Bring real analytical rigor to how Growth invests — attribution, LTV, and testing/experimentation discipline — so decisions about where to deploy resources are tied clearly to business impact
- Close the gap between Growth R&D and go-to-market: build the mechanisms (shared roadmap, dependency tracking, decision forums) that let both orgs operate as one team working toward the same number, rather than two orgs trading requests
- Design an operating system anchored in technology vs. humans: build the muscle and mechanisms the Growth org can through automation, and hand off ownership once a system is running
- Act as a trusted advisor to Growth leadership: pressure-test strategy, surface risks and blind spots early, and bring an opinionated point of view, not just facilitation
- Use AI as a default, not an add-on: build reusable, AI-powered workflows for planning, synthesis, and reporting so manual coordination is the exception, not the norm
- Spot when a team is optimizing for the wrong thing: recognize when more effort against the current approach won't get us where we need to go, and push teams toward a fundamentally different path rather than a marginal improvement
- Raise the bar for how I&O operates, not just how Growth operates: share what's working, question what isn't, and help the broader I&O team build a stronger, more consistent craft
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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