Head of ML/AI Engineering

About the Role:

Gusto sits at the center of many of the most important workflows for small businesses which creates a meaningful opportunity to use rich product and customer data to build AI- and ML-powered systems that improve customer experiences automate complex work support better decision-making and help small businesses thrive. As Gusto becomes more AI-native we are evolving how AI ML risk modeling and platform capabilities come together across our products and internal systems.

We are seeking a strategic Head of AI/MLE to lead this next chapter. In this key leadership role you will define how Gusto builds deploys evaluates and scales AI/ML systems across the company. You will lead a broad organization spanning Machine Learning Engineering ML Platform Risk Data Science and AI Scientists while partnering closely with senior business leaders to shape where AI can create durable customer and business impact.

As the Head of AI/MLE at Gusto you will be responsible for unifying classical ML and GenAI into a coherent technical strategy maturing the platform for broader self-service adoption and shaping how AI-native products and production systems are built at Gusto. Your teams will help translate business problems into end-to-end AI/ML systems from experimentation and prototyping through evaluation deployment monitoring feedback loops and operational governance.

Your leadership will be critical in setting the technical direction operating model and quality bar for AI at Gusto. You will help teams move quickly where speed and learning matter most while ensuring production systems meet high standards for reliability measurement safety and long-term maintainability. This is a senior technical executive role for someone who can combine deep engineering credibility strong business judgment and executive-level influence to make AI a durable advantage for Gusto.

Here’s what you’ll do day-to-day:

• Lead manage and develop a broad AI/MLE organization spanning Machine Learning Engineering ML Platform Risk Data Science and AI Scientists fostering a culture of technical excellence customer impact collaboration and continuous learning.
• Define and execute Gusto’s AI/ML systems strategy unifying classical ML GenAI risk modeling and platform capabilities into a coherent approach that supports Gusto’s broader business and product goals.
• Partner with senior leaders across Product Engineering Design Data Risk Legal Security and business teams to identify where AI/ML can create meaningful customer value business impact and operational leverage.
• Shape how AI-native products and internal systems are built at Gusto helping teams translate business problems into end-to-end AI/ML systems with clear standards for evaluation monitoring observability reliability safety governance and long-term maintainability.
• Lead the development and maturation of AI/ML platform capabilities tooling primitives guardrails and deployment patterns that make it easier for product and engineering teams to build evaluate deploy and operate AI/ML systems with less friction more autonomy and the right quality bar.
• Drive disciplined technical and business judgment around AI/ML investments including where to build where to leverage existing capabilities and where to avoid unnecessary complexity.
• Create room for fast experimentation and learning where appropriate while ensuring high-impact production systems meet strong standards for quality operational rigor and business accountability.
• Set clear goals KPIs and operating rhythms to measure the performance adoption and business impact of AI/ML systems and communicate progress and tradeoffs clearly to senior leadership.
• Stay close to the frontier of AI/ML advancement and help Gusto apply new technologies pragmatically with strong judgment about what is durable useful and ready for production.

Here’s what we're looking for:

• We love meeting people with different technical and leadership backgrounds. For this role we are looking for 10+ years of experience leading teams in applied machine learning AI engineering or data science roles with a track record of delivering impactful customer-facing software solutions.
• Deep technical expertise across AI/ML systems including classical ML GenAI/LLMs statistical modeling risk modeling and production-scale deployment.
• Strong software engineering and systems background with the ability to lead technical strategy across data retrieval evaluation deployment routing monitoring observability feedback loops and lifecycle management.
• Experience leading and scaling high-performing technical organizations including Machine Learning Engineers AI/ML Platform teams Risk Data Scientists and/or AI Scientists.
• Experience evolving ML teams toward a stronger software engineering and systems orientation with clear ownership for building operating and improving production AI/ML systems.
• Strong platform orientation with experience building tools primitives guardrails and self-service capabilities that help product and engineering teams build AI/ML-powered products safely and effectively.
• Executive-level strategic judgment with the ability to shape company-level AI/ML priorities align senior leaders around tradeoffs and make clear investment decisions based on customer value business impact technical feasibility risk data readiness and operational complexity.
• Strong executive communication and influence with the ability to explain complex AI/ML concepts and technical decisions in a way that clarifies strategy tradeoffs risk investment needs and organizational implications.
• Experience operating as a peer to senior cross-functional leaders across product engineering design data risk legal security and business teams — bringing clarity urgency and practical judgment to ambiguous company-level opportunities.
• A clear thesis on how classical ML and GenAI should work together how modern AI platform capabilities like retrieval evaluation agents and observability should come together and how AI/ML teams should evolve as the field becomes more software- and systems-oriented.
• Experience in fintech risk modeling regulated environments or domains with high standards for reliability trust and compliance is a plus.
• Advanced degree in computer science data science machine learning statistics or a related field is a plus but demonstrated systems leadership production judgment and executive-level impact matter most.

Our cash compensation amount for this role is targeted at $245000-272000 in Denver & most remote locations and $288000-321000 for San Francisco & New York. Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.

What We Do

Gusto is a modern online small business platform that helps small businesses take care of their teams. On top of full-service payroll Gusto offers health insurance 401(k)s expert HR and team management tools. Today Gusto offices in Denver San Francisco and New York serve more than 400000 businesses. Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds not just because it's the right thing to do but because it makes our company stronger. If you share our values and our enthusiasm for small businesses you will find a home at Gusto.

Why Work With Us

We help small businesses—the backbone of the economy—thrive. Everything we do ladders up to empowering entrepreneurs and supporting their teams. Gusto empowers builders at every level to take initiative and make things better. You'll be solving meaningful challenges that shape the future of work.

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