Senior AI Engineer, Justworks
AI Frontiers
$188-242k
Datadog
Senior and Expert level
New York
Business operations platform
Job no longer available
Business operations platform
1001+ employees
FintechB2BEnterpriseHRCompliancePaymentsSaaS
Job no longer available
$188-242k
Datadog
Senior and Expert level
New York
1001+ employees
FintechB2BEnterpriseHRCompliancePaymentsSaaS
Company mission
To help entrepreneurs and businesses grow with confidence.
Role
Who you are
- You're an engineer who gets energized by hard problems that don't have a predetermined solution — and you know how to ship your way to an answer
- You've built production systems, navigated real infrastructure, and learned to move fast without leaving a mess
- You pick up new domains quickly and use that understanding to build solutions that fit
- You see frontier AI not as something you're experimenting with but as the means by which we transform an org
- You're insatiably curious, never satisfied leaving a system the way you found it, and you know how to evaluate whether an AI system is actually working — not just whether it runs
- Impact matters more to you than the tools you used to get there; you center the customer even when you're building internal tooling
- Camaraderie - Day to day you can be seen working together toward a higher purpose. You like to have fun. You’re an active listener, treat people respectfully, and have a strong desire to know and help others
- Openness - Your default is to be open. You're willing to share information, understand other perspectives, and consider new possibilities. You’re curious, ask open questions, and are receptive to thoughts and feedback from others
- Grit - You demonstrate grit by having the courage to commit and persevere. You’re committed, earnest, and dive in to get the job done well with a positive attitude
- Integrity - Simply put, do what you say and say what you'll do. You’re honest and forthright, have a strong moral compass, and strive to match your words with your actions while leading by example
- Simplicity - Be like Einstein: “Everything should be made as simple as possible, but no simpler.”
- 6+ years of professional hands-on software engineering experience
- Full-stack or backend engineering depth - shipped and maintained production systems, not just prototypes
- 2+ years, 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
- Experience designing and running evals: you know how to define what "working" means for an AI system and build the measurement scaffolding to prove it
- Familiarity with LLM observability tooling (LangSmith, Datadog LLM monitoring, or equivalent):you instrument what you build and use signal to improve it
- Track record of working across functions: partnered with non-engineering stakeholders, understood their problem domain, built something that fit
- Strong written and verbal communication with non-technical audiences — you can explain a technical tradeoff to an ops lead without losing them
- Comfort with ambiguity: you scope your own work, write your own briefs, and don't need a detailed spec to get started
- Nice to have: practical machine learning experience: familiarity with model behavior, data quality, iteration loops, and how those fundamentals translate into building reliable AI systems
What the job involves
- The Data & Analytics team is Justworks' data and AI center of excellence — a connected set of functions spanning business intelligence, data science, analytics engineering, platform data/ML engineering and AI builders
- We've grown significantly over the last several years and continue to build momentum across the business, leveling up maturity in how we deliver insights, govern data, and enable the company to make better decisions. You'll find a highly collaborative & diverse group motivated by craft, shared learning, and a genuine commitment to growing our impact for customers while evolving how we work together for our people. Come build with us!
- Justworks is looking for a Senior AI Engineer to join AI Frontiers, a small internal consultancy that finds where AI creates step-change improvements across the company — builds the thing, gets it to production, and transfers it to the team that will own it
- You'll move across business functions as a functional accelerator, resolve AI-specific systems gaps nobody else is moving on, and read what's emerging externally before it becomes obvious inside
- You build, prove the pattern, and hand off
- Technical execution is table stakes
- The harder skill is navigating ownership, alignment, and organizational complexity while still shipping
- Drop into business functions to identify where AI has the highest leverage, define what to build, and own the full arc from scoping through handoff
- Spot and resolve AI-specific systems gaps across the org - missing shared infrastructure, fragmented adoption patterns, absent measurement benchmarks - and move on them faster than the rest of the org could
- Scan externally for emerging AI capabilities and market patterns; translate signal into written briefs that inform what the team experiments on next
- Build AI-powered tools and pipelines using frontier models, agent frameworks, and LLM infrastructure as core building blocks, not experiments
- Design and implement evaluation frameworks (evals) to measure whether AI systems are performing as intended — not just technically functional but meaningfully useful
- Instrument AI systems for observability: logging, tracing, cost tracking, latency monitoring, and anomaly detection using tools like Datadog, LangSmith, or equivalent
- Navigate cross-functional ownership dynamics: identify the right stakeholders, build alignment, and hand off in a way that sticks
- Represent AI Frontiers in cross-functional forums and executive reviews as a credible voice on what AI can and can't do
- Perform other related responsibilities as needed based on department and/or organizational needs
- In the Senior AI Engineer role, how results are achieved is paramount for your success and ultimately result in our success as an organization. In this role, your foundational knowledge, skills, abilities and personal attributes are anchored in the following competencies:
- Plans & Aligns - Ensures individual actions support company mission; communicates effectively; understands urgency and plans accordingly
- Balances Stakeholders - Understands internal and external stakeholder requirements, expectations, and needs and acts fairly despite conflicting demands of stakeholders
- Influence and Leadership - fostering a community of knowledge-sharing, collaboration, mentorship, and forward-thinking across the organization
- Manages Complexity - Making sense of complex, high quantity, and sometimes contradictory information to effectively solve problems
- Good Judgment - Pauses before acting; asks questions to fully understand context; applies critical thinking and takes ownership of outcomes
- Teamwork & Communication - Honors diverse thoughts and opinions; leverages unique skills to maximize efficiency
- Skills and Knowledge - the capacity to actively learn and apply specific domain knowledge, know-how, and best practices to continually enhance and improve
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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