Benefits Operations Chief of Staff, Gusto
$152-210k
Salary dependent on location
More information about location
2+ days a week in office
Automated payroll, benefits & HR platform
Job no longer available
Automated payroll, benefits & HR platform
1001+ employees
Job no longer available
$152-210k
Salary dependent on location
More information about location
2+ days a week in office
1001+ employees
Company mission
To create a world where work empowers a better life.
Role
Who you are
- 10+ years of total experience in analytical, operating roles at high-growth startups
- 5+ years in a CX Strategy or Senior-Level CX Operating Experience
- Experience as CoS or CX Strategy lead in a large tech company, working with CX or Product leaders
- Exposure to scale of 1000+ employee organizations with a mix of exempt and non-exempt workforce
- Industry: meaningful work in tech (can’t be the first time)
- Business builder mindset
- Empowered a team of 2+
- Demonstrated ability to mentor / advise execs on people topics
- Stellar program management: you will be called on to develop, and manage programs for BenOps-wide initiatives
- Deep empathy and obsession for small business customers
- Grit, hustle, and the ability to flex into problems at all altitudes
- The ability to keep all the trains on the tracks and the clear communication flowing
- A deep passion for helping others
- Prior chapter outside of Tech is a nice to have
What the job involves
- This is a leadership role that will work closely with cross-functional teams to support the execution of high-priority projects, align teams around shared goals, and ensure business continuity
- As part of a fast-paced, high-growth environment, the Chief of Staff will have the opportunity to shape and scale a high-performing organization, while directly influencing key outcomes and driving transformational change
- The Chief of Staff to the Head of Benefit Operations will play a pivotal role in driving strategic initiatives, operational excellence, and organizational alignment for the department, ensuring seamless execution across all business functions
- This person will be responsible for overseeing the creation and execution of key business strategies, managing OKRs, streamlining workflows, and driving change management initiatives to ensure continuous improvement in customer experience and operational efficiency
- Partner with the department head to drive strategic initiatives, ensuring alignment with company goals and cross-functional teams
- Act as a strategic advisor to leadership, providing guidance on decisions, trends, and growth opportunities
- Own OKRs, performance reviews, and operational cadence, ensuring alignment and progress across BenOps and leadership
- Lead change management initiatives, ensuring readiness for process changes and driving adoption across the organization
- Develop and maintain workflows, metrics, and dashboards to drive operational efficiency and consistency across teams
- Oversee centralized intake and prioritization of product requests for BenOps, providing clear recommendations on product asks
- Use data-driven insights to improve customer experience and drive continuous improvements across BenOps and CX
- Step in to manage teams as needed, ensuring business continuity during transitions or high-demand periods
- Manage organizational communications, including newsletters, All Hands updates, and team-related announcements
- Enable senior managers and foster a culture of accountability, engagement, and continuous learning across the organization
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
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 values
- Embody a service mindset - Never stop advocating for the needs of others
- Dream big, then make it real - Be ambitious. Show and do, rather than tell and talk
- Be proud of the how - Ensure deep integrity in everything you do
- Embrace an ownership mentality - Take initiative to leave things better than you found them
- Debate then commit - Share openly, question respectfully, and once a decision is made, commit fully
Company HQ
Central Waterfront, San Francisco, CA
Articles
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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