Senior AI Enablement Engineer, Justworks
People
$166-214k
Snowflake
Datadog
Senior and Expert level
New York
2+ days a week in office
Business operations platform
Be an early applicant
Business operations platform
1001+ employees
FintechB2BEnterpriseHRCompliancePaymentsSaaS
Be an early applicant
$166-214k
Snowflake
Datadog
Senior and Expert level
New York
2+ days a week in office
1001+ employees
FintechB2BEnterpriseHRCompliancePaymentsSaaS
Company mission
To help entrepreneurs and businesses grow with confidence.
Role
Who you are
- You have a track record of shipping internal tools and AI-powered workflows that people actually use
- You're as comfortable mapping a team’s AI gaps and designing a solution as you are vibe-coding a working prototype with an AI agent
- You're insatiably curious and never satisfied with the status quo — you operate with urgency and agency, center the customer in every decision, and make every team you join better
- You think in systems, move fast, and know how to bring people along without manufacturing consensus
- You don’t need to come from HR. You need to care about building tools that make people’s work lives better
- This is a true engineering role. We are looking for someone with production experience shipping AI systems — not someone who uses AI tools, but someone who builds them. Senior here means senior by organizational reach and shipped impact, not by years of CS experience
- 6+ years of professional, hands-on builder/software engineering experience
- 2+ years of hands-on experience building with LLMs and AI tooling in production: agent frameworks, pipelines, retrieval systems, or AI-integrated workflows that real users depend on
- Familiarity with LLM observability tooling (LangSmith, Datadog LLM monitoring, or equivalent): you instrument what you build and use signal to improve it
- Systems-level understanding of data retrieval with comfort working with vector embeddings and combining structured data, such as Snowflake tables, with unstructured text to power intelligent, context-aware internal tools
- Strong working knowledge of data privacy standards, including experience building audit trails, role-based permissions, and robust access controls for highly confidential datasets
- Familiarity with HR/People systems such as Workday or Greenhouse is a meaningful plus, but not required
- Strong communication skills — able to present technical options, trade-offs, and progress to non-technical People and business stakeholders
- Demonstrated ability to work independently in ambiguous, greenfield environments: defining scope, sequencing work, and driving to production without heavy oversight
What the job involves
- Reporting to the Senior Manager, People Strategy Operations, the Senior AI Enablement Engineer, People, is a technical founder embedded within the People function
- Building the Core AI & Automation Layer (~50%)
- Drive the technical execution of the People team's AI transformation roadmap—architecting, building, and maintaining intelligent solutions around our prioritized operational workflows
- Build agentic workflows, RAG pipelines, and system integrations required to scale workflows from ‘Human + AI handoffs’ to ‘AI as a system’ level maturity
- Scan externally for emerging AI capabilities and market patterns; translate signal into written briefs that inform what the team experiments on next
- Embed long-term operational success by creating reproducible blueprints, demos, and guides that naturally transfer expertise and cultivate sustainable AI ownership across the People team
- Data Layer & AI Reliability (~25%)
- Partner with the People Analyst and Senior Manager of Data Management & Governance to deeply understand the existing Snowflake data model to identify what is trusted, what is fragile, and what the AI layer can reliably consume
- Assess the custom Workday-to-Snowflake pipeline to understand its architecture and engineering limitations, ensuring any AI tools built on top of it are designed to handle data quirks reliably
- Design evaluation frameworks to measure the accuracy, latency, and real-world utility of AI tools, including hallucination rates, retrieval precision, and user satisfaction, to iterate based on those signals
- Implement data privacy and access controls appropriate to highly sensitive people data, including PII handling, role-based access, and audit trails in close coordination with the Data Governance team
- Technical Partnership & Responsible AI (~25%)
- Serve as the primary technical thought partner to the Senior Manager of Strategy Operations to translate People strategy and operational pain points into scoped, sequenced engineering work
- Collaborate with core engineering and data teams to align on infrastructure, security posture, and standards to ensure People-built systems are enterprise-grade and maintainable by others
- Proactively surface risks, limitations, and failure modes in AI systems before they impact employees by building with an explicit lens on fairness, auditability, and responsible deployment in a workforce context
- Stay current on the AI engineering landscape by evaluating new models, frameworks, and tooling as they become relevant while bringing a strong point of view on when to adopt versus wait
- In this role, success means delivering reliable, production-grade AI tools that reduce manual work, unlock better workforce insights, and create a more seamless experience for every Justworks employee. Through end-to-end technical ownership and thoughtful partnership, this engineer will build the foundation for the People team to use AI responsibly, confidently, and at scale
- Success in this role is defined not only by what you ship, but how you ship it. Core capabilities include:
- Technical Craft — writing clean, tested, maintainable code; making sound architectural decisions; and building systems that hold up in production, not just in a demo
- Problem Translation — taking ambiguous People team needs and converting them into well-scoped technical solutions with clear success criteria and measurable outcomes
- Plans and Aligns — breaking down complex builds into sequenced milestones; communicating progress and blockers proactively to non-technical stakeholders without being asked
- Initiative and Motivation — identifying what needs to be built before being asked, and driving it from whiteboard to production without heavy supervision
- Teamwork and Communication — documenting systems thoroughly, collaborating across engineering and People, and explaining technical trade-offs in plain language to people who don’t write code
Our take
Justworks operates in an increasingly crowded space of all-in-one business operation suites, that include tools like human resources, payroll, employee management, benefits, and others that businesses critically need to operate as they scale.
Globally, human resource management has become an extremely fertile field, creating great opportunity for Justworks to continue to grow. The company is regarded as a market leader, but does see competition in the shape of Paychex Flex, Rippling, Paylocity, and TriNet, among others.
Justworks' solutions have proven extremely popular with SMEs, and this has not gone unnoticed by investors - with the company picking up considerable amounts of funding. The company is known to have sights on going public, though these were delayed somewhat by market conditions. That said, it has continued to expand operations and acquired Via in 2024, signalling that its going strong.
Steph
Company Specialist at Welcome to the Jungle
Insights
Top investors
24% employee growth in 12 months
Company
Funding (last 2 of 7 rounds)
Nov 2023
$16.9m
LATE VC
Jan 2020
$50m
SERIES E
Total funding: $159.9m
Company benefits
- Paid volunteer work
- Paid parental leave
- Work from home opportunities
- Medical, dental, and vision insurance, plus access to One Medical, Kindbody, and Teladoc
- Premium access to Headspace, ClassPass stipends, and webinars to support your overall wellness on topics like nutrition, budgeting, mindfulness, and more
- All Justworks offers include equity, and Justworkers can continue to earn more over time with promotions and tenure
- Extensive learning & development opportunities through workshops, ExecOnline, Udemy, and BetterUp coaching
- Apprenticeship program that supports internal movement and growth
Company HQ
Fulton Ferry District, NY
Leadership
Isaac Oates
(Founder & Director)Experience as a Senior Product Manager at Amazon before founding Adtuitive and serving as COO for a year. Left this position to spend 3 years as a VP at Etsy, before founding Justworks.
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