Insights & Operations Partner, 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 create a world where work empowers a better life.
Role
Who you are
- This is a generalist role for someone who thrives in fast-paced, high-autonomy environments and has a proven track record of delivering results on large technical programs, especially those requiring deep coordination, systems thinking, and comfort with navigating uncertainty
- 6+ years of experience in technical strategy, operations, engineering program management, or chief of staff roles in fast-paced tech environments
- Proven ability to drive clarity, alignment, and action across multiple teams and stakeholders
- Strong systems thinker with experience designing processes that scale
- Proven ability to lead cross-functional technical initiatives at scale
- Strong project management skills—able to manage multiple workstreams and timelines simultaneously
- Excellent written and verbal communication, including executive-facing storytelling
- Confident in handling high ambiguity and in operating across technical and business domains
- Excellent written and verbal communication skills, including ability to drive outcomes across leadership stakeholders
- Experience with resource allocation, headcount planning, or capital investments
- Nice to have: MBA and/or consulting background, previous experience in Chief of Staff-style roles, or experience in product/engineering orgs at growth-stage companies
What the job involves
- We are looking for a highly capable and versatile leader to join the Engineering organization as an Insights & Operations (I&O) Partner
- In this role, you’ll drive complex, strategic programs that span multiple teams and domains—serving as an execution partner to Engineering and Product leaders
- You will create clarity from ambiguity, orchestrate collaboration across functions, and ensure the operational infrastructure of Engineering scales effectively as Gusto grows
- Gusto’s Engineering organization builds the infrastructure and product capabilities that power our platform for small and medium-sized businesses
- Within Engineering, the Insights & Operations (I&O) team serves as a connective tissue → working across teams, systems, and priorities to bring alignment, transparency, and momentum to our most important technical initiatives
- Day to day this role will design and lead strategic and operational programs that improve execution across Gusto’s 400+ person engineering org
- Own initiatives such as capital and headcount planning, operating model changes, cross-team delivery coordination, and systems that improve roadmap alignment
- Serve as a trusted thought partner to senior technical leaders, helping to translate vision into systems of execution
- Drive operational excellence by designing and continuously improving our team rituals, artifacts, and planning processes
- Develop durable programs and decision-making frameworks to scale planning, investment, and prioritization
- Build strong partnerships with teams across Product, Data, Finance, and People to ensure alignment on org-wide goals and initiatives
- Apply structured problem-solving and systems thinking to ambiguous and high-impact organizational challenges
- Lead projects such as:
- Creating a framework for how Gusto approaches monolith extraction
- Standing up a coordination model for AI/ML platform initiatives
- Redesigning how technical priorities are surfaced and evaluated across crafts
- Manage and prepare content for executive-level forums (e.g. Engineering All Hands, QBRs, planning readouts) with a strong attention to accuracy and narrative clarity
- Dive deep into technical areas when necessary to help drive alignment and unblock execution
- Track and support ongoing compliance and operational requirements across the year
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 three co-founders of Gusto – all coming from small business backgrounds – collaborated on a Fintech company 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 200,000 customers and a multi-billion dollar valuation. In 2021, Gusto began acquiring other companies to strengthen its offering and its position in a competitive market, including two other fintech startups, Ardius and Symmetry.
Through its continued acquisitions and fundraising efforts, the company has carved out a strong position for itself in the space. Although Gusto has found itself impacted by the macroeconomic situation, through the significant effect it has had on its clientele, the company still appears positive for the future after raising funds in 2023 that will see it reach key profitability benchmarks. It continues to consolidate its platform, for example by integrating with OpenComp to grant its users access to the company's Compensation Intelligence Platform.
Steph
Company Specialist at Welcome to the Jungle
Insights
45% employee growth in 12 months
Company
Funding (last 2 of 8 rounds)
May 2022
$55m
SERIES E
Aug 2021
$175m
SERIES E
Total funding: $706.1m
Company benefits
- Comprehensive medical, dental, and vision benefits, plus a variety of mental health resources
- Flexible vacation - Gusties are encouraged to take the time off they need to continue doing great work
- Fertility treatments, parental leave, pregnancy termination, caregiving, gender-affirming surgery, hormone treatments, transgender-inclusive services, and more
- If you work at one of our homebases, enjoy food, drinks, and good conversation — on us
- Celebrate 5 or 10 years at Gusto and take a month off to recharge
- Take advantage of internet, phone, commuter, and wellness stipends each month, along with a WFH stipend and cash for anniversaries
Company HQ
Central Waterfront, San Francisco, CA
Leadership
Joshua Reeves
(CEO)Studied Electrical Engineering at Stanford and went onto co-found Gusto in 2011.
Tomer London
(CPO)Has a PhD in Electrical Engineering from Stanford. Was a Researcher at Intel, and then interned at Bump Technologies. Co-founded Vizmo, a mobile self-service technologies company, in 2008. Co-founded Gusto in 2011.
Edward Kim
(Head of Engineering)Studied Electrical Engineering at Stanford. Was Senior Project Engineer at Volkswagen of America Electronics Research Lab and then co-founded Picwing, a printed photos company, in 2008. Co-founded Gusto in 2011.
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