Head of Machine Learning and AI, Gusto

• 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

• 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

• 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

Total funding: $706.1m

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.