About Freehand
Most AI companies are building tools. We're building the worker.
Freehand's AI agents replace the human decision-making and coordination layer that sits above enterprise software — handling the analysis, negotiation, prioritization, and execution that previously required armies of logisticians / supply chain professionals.
Our customers include Apple, Meta, GE, Pfizer, J&J, Schlumberger, Cardinal Health, and Unilever. They chose us because we have a fundamentally different answer to what enterprise software looks like when AI can do the job.
If you want to work on something that matters, with people who will push you to be sharper than you thought you could be, this is the place.
The Role & The Team
At Freehand, we believe Talent is a real moat for a startup. And therefore, the People & Culture team has a key seat at the table in defining the future of the organization.
In this role, you'll be the second person on the People team at a Series C AI company that's growing fast, operating across two geographies, and shaping global practices on what work can look like in the age of agentic AI.
You'll work closely with the Head of People & Culture across the full people spectrum: hiring exceptional talent and building the culture and systems that retain them.
What You'll Do
Own talent acquisition across functions — Tech, GTM, and Professional Services — from sourcing strategy through close
Partner with hiring managers and leadership to build and move hiring pipelines without sacrificing bar
Work closely with the Marketing team to drive global Employer Branding initiatives for Freehand
Drive employee experience initiatives that make Freehand a place top talent chooses to stay
Build and automate key HR processes — onboarding, performance management, engagement — using AI tools to do more with less
Support people partnering across both geographies: handling employee relations, manager coaching, and org design questions as they come up
Help navigate the operational and compliance complexity of a US-India setup, including our EOR infrastructure
Work with the Head of People to define what the people function looks like at an AI-native company — org design, workforce planning, and the harder questions about human + agent collaboration
Who You Are
6–9 years across HR and talent acquisition, ideally spanning both functions rather than just one
Have supported employees in the US and are comfortable with US employment law and HR practice
Genuinely fluent with AI — and have actually used it to automate or meaningfully improve an HR process, not just experimented with it
Have worked across multiple functions: you're as comfortable hiring an enterprise AE as you are a Staff Engineer or a Customer Value Lead
Exposure to EOR setups is a strong plus
You operate well with ambiguity and a lean team; you don't need a ton of structure & resources to exist before you can move, and can set up reliable processes on a white canvas
You're a strong enough generalist to stretch across people partnering and TA, but sharp enough that leaders trust your judgment on both
Working at Freehand
Series C, ~100 people across the US and India. Big enough to have infrastructure, small enough that your work is visible. We run on five core operating principles; these are not values-on-a-wall, this is the exact philosophy we built our AI agents on :
Context Before Confidence. We get in, ask (a ton of) questions, connect the dots ourselves and move fast. No passengers, no hand-holding. The amount of confidence you'll have in Week 1 is directly proportional to the context strive to gain.
Decisions, not Recommendations. Freehand folks decide, they don't present options. You'll have real autonomy, and real accountability to match.
High Agency, High Trust. We won't manage you closely or ask you to escalate every call. Act, share your reasoning, and course-correct when needed. That's the contract.
Accountability is the Product. When something goes wrong — and it will — we name it, learn from it, and move on. No politics, no cover. Just fix it.
The Work That Remains is the Work That Matters. We actively cut low-value work. What lands on your plate is there because it matters — and can only be done by you.
It's a small world. Freehand employees Work Anywhere across US & India (we're remote & travel-first). As and when required, for this role, we will also arrange for a fully-paid trip to our HQ in Chennai to meet & interact with cross-functional teams.
In addition, we proudly offer the following Benefits to all our full-time employees:
Full Health coverage (accidental, life, vision, dental & health consultations)
Monthly home-internet costs
Flexible working hours
Complimentary food & snacks at the Chennai HQ
Equal Opportunity
Freehand hires on merit — your thinking, your track record, your potential — without regard to race, gender, age, religion, sexual orientation, national origin, disability, or any other protected characteristic. If you meet most of the criteria above but not all of it, apply anyway. We care more about your willingness to learn & take initiative than whether your resume maps perfectly to every line.
