Senior Engineering Manager, Gusto
Growth, Onboarding & Activation
$185-275k
US Salary dependent on location. $200,000 - $250,000 CAD for Toronto, Canada
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
$185-275k
US Salary dependent on location. $200,000 - $250,000 CAD for Toronto, Canada
2-3 days a week in office
1001+ employees
Company mission
To grow the small business economy.
Role
Who you are
- 12+ years of professional software development experience
- 5+ years of engineering management experience, preferably revenue-driving teams Product engineering teams or Growth teams
- Experience managing multiple teams, and managing EMs
- Curiosity and ability to operate in an AI-native environment — integrating intelligence, automation, and experimentation into how we grow the business
- Experience in highly cross-functional environments for highly complex products
- Experience in scaling Engineering organizations
Desirable
- Experience building and maintaining onboarding experiences and package recommendations
- Experience in experimentation and user experience optimization
- Experience working cross-functionally with Revenue teams
- Experience incorporating AI and ML into product experiences
What the job involves
- As Gusto transitions to an AI-native company, this role will help shape how intelligence is embedded across our Growth platform — from acquisition to onboarding to expansion
- You’ll lead engineering efforts that make our systems adaptive, data-driven, and intelligent by design
- This means building not only for scale and reliability, but for learning and continuous optimization — where every part of the funnel can reason, predict, and personalize
- You’ll operate at the intersection of Growth systems, AI capabilities, and platform evolution to help unlock Gusto’s next phase of sustainable revenue growth
- Build and foster an inclusive, collaborative, and impact-oriented culture
- Collaborate closely with Product, Design, and Data Science to define, iterate, and execute on initiatives contributing to revenue growth
- Champion AI-native patterns in Onboarding platform — designing for learning loops, feedback-driven iteration, and safe model usage in customer-facing contexts
- Help establish and guide the team on best practices for experimentation, evaluation, and observability in AI-augmented Growth experiences
- Collaborate with AI platform and data science teams to integrate model-driven insights into Onboarding workflows — such as onboarding personalization, intelligent package recommendations, and AI-driven experiences that answer user’s questions while helping them accomplish their tasks
- Engage with all development teams across Gusto to align and drive towards long-term maintainability and stability of our systems
- Mentor and provide guidance to individual team members, fostering growth and development
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 400,000 customers and a multi-billion dollar valuation. And 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 has seen it reach key profitability benchmarks. It continues to expand its platform, most recently partnering with Parafin to launch a payroll line of credit for small businesses. With a growing suite of services and a clear focus on supporting small businesses through changing economic conditions, Gusto looks set to sustain its momentum and further strengthen its position in the HR and payroll technology market.
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
- Health and Wellbeing: 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.
- Time Away: It's important to take time away for yourself or to take care of your family. Gusto offers paid vacation, sick time, bereavement, and holidays, paid leaves, sabbatical, and more!
- Free meals and refreshments: If you work at one of our offices, enjoy food, drinks, and snacks— on us. Conversation and community is an added bonus!
- Perks:
Company HQ
Central Waterfront, San Francisco, CA
Leadership
Joshua Reeves
(Co-Founder & CEO)Studied Electrical Engineering at Stanford and went onto co-found Gusto in 2011.
Tomer London
(Co-Founder & 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
(Co-Founder & 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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