Head of Machine Learning and AI, Gusto
$222-299k
Salary variable on location
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
$222-299k
Salary variable on location
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
- We love meeting people with different data backgrounds. For this role, we are looking for 8+ years of experience leading teams in applied machine learning, AI, or data science roles, with a track record of delivering impactful software solutions
- Strong expertise in machine learning techniques, statistical modeling, and AI technologies, with hands-on experience in deploying models at scale
- Strong software engineering literacy and able to lead and grow a technical team of Machine Learning Engineers
- Excellent leadership and people management skills, with the ability to inspire and grow high-performing teams
- Strong collaboration and communication skills, with experience working closely with engineering, product, and business teams to deliver end-to-end solutions. Capable of translating complex ML/AI concepts into actionable business strategies, and an ability to influence product teams roadmaps
- Strategic thinker with a business-first mindset, able to build a vision for the future that inspires
- Deep understanding of ML operations (MLOps) practices, including model monitoring, retraining, and lifecycle management
- Experience in risk modeling or working within regulated environments is a plus
- Excellent communication skills, with the ability to present complex technical ideas to both technical and non-technical stakeholders
- Passion for responsible AI practices and a commitment to ethical AI development
- Advanced degree in computer science, data science, machine learning, or a related field is a plus
- Experience in the Fintech industry or risk management domain is a plus
What the job involves
- We are seeking a strategic Head of Machine Learning and AI, to lead a newly carved out function at Gusto
- In this key leadership role, you will work with senior Product, Engineering and Design stakeholders to build better customer experiences and improve operations, aligning ML/AI use cases to our broader organizational goals and spearheading the culture of ML/AI throughout our product
- Reporting to the Head of Data, you will also collaborate closely with cross-functional platform teams, including the ML Engineering Platform team and AI Platform team, to ensure that our ML/AI initiatives are scalable and robust
- The Risk Data Science and Analytics team will also roll up within this organization, with the Head of Risk Data reporting to this role
- As the Head of ML/AI, your team will own the end-to-end lifecycle of ML/AI projects—from ideation to production
- You will oversee the delivery of data-driven insights and predictive models that improve decision-making, optimize processes, and mitigate risk
- Your leadership will be critical in shaping the future of ML/AI within Gusto, setting strategic direction, and building a high-performing team of ML/AI practitioners
- Lead, manage, and mentor both the Applied ML/AI and Risk Data Science teams, fostering a culture of innovation, collaboration, and continuous learning
- Define and execute the strategy for Applied ML/AI across the organization, ensuring alignment with business objectives and measurable impact
- Collaborate closely with the ML Engineering Platform and AI Platform teams to ensure seamless integration and deployment of models into production environments
- Oversee the design, development, and deployment of machine learning models and AI solutions that address key business challenges
- Partner with key stakeholders across product, engineering, and business units to identify opportunities for ML/AI-driven improvements and innovations
- Drive the adoption of best practices in model development, including monitoring, retraining, and ensuring compliance with relevant ethical and regulatory guidelines
- Advocate for responsible AI usage and establish frameworks for fairness, transparency, and accountability in all ML initiatives
- Establish KPIs and metrics to track the performance and business impact of ML solutions, reporting regularly to senior leadership
- Manage team resources, budgets, and timelines to ensure successful delivery of projects and initiatives
- Work with the AI Platform team to stay abreast of the latest developments in machine learning and artificial intelligence, ensuring the company remains at the cutting edge of innovation
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 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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