The RoleWe're looking for our first dedicated Recruiter to help accelerate Letter's growth. We've hired 40+ Letterheads since the beginning of the year and are looking to double our ~60-person team in the coming months.
You'll own our day-to-day recruiting engine, finding and engaging great candidates, running fast and high-touch interview processes, and partnering with our People Ops Lead and busy hiring managers to continuously improve how we hire.
What You'll Do- Own recruiting end-to-end, from inbound review and active sourcing through screens, interviews, offers, and close
- Coordinate a high volume of fast-moving interviews and be present in-office to ensure onsite interviews run smoothly and candidates have a great experience
- Partner with hiring managers to launch roles, define ideal candidate profiles, and build and continuously improve job postings, interview plans, and exercises
- Source exceptional candidates directly and identify the channels, job boards, and tools that help us reach the best talent
- Help establish consistent, high-signal interviewing practices, including competencies, interview questions, feedback, calibration, and training
- Partner with our People Ops lead to continuously improve our TA tech stack, recruiting processes and automations, and employer brand
Qualifications for the Role- 5+ years of recruiting experience, ideally in a fast-growing startup or similarly high-velocity, hypergrowth environment
- Strong full-cycle recruiting experience across direct sourcing, screening, interview management, and closing
- Strategic and hands-on; you can help shape how we recruit while jumping in to solve a last-minute interview change
- Thoughtful about recruiting processes and systems, but biased toward simple, practical solutions that help teams move faster
- High ownership and bias for action; you see what needs to be done, jump in, and continuously look for ways to make things better
Why Join?- Exponential Growth Potential: Be part of an early-stage startup in a transformational space, where there's massive opportunity for expansion and your contributions can significantly influence the company's trajectory.
- Autonomy & Impact: You'll have the freedom to make key decisions, experiment with new approaches, and truly own your role.
- AI-Powered Platform: Work at the forefront of AI technology, helping revenue and enablement teams deliver real impact with AI (see our work with Lenovo and Aftership).
- Build from the Ground Up: This is a rare opportunity to be part of something bigger, crafting and shaping the People function for a fast-growing startup - we're being recognized as the fastest-growing AI startup in Chicago and recently won 1871's Momentum Award
How We OperateAt Letter AI, we operate by a set of core principles:
- Customer-obsessed: Make our customers unreasonably happy and everything else will fall into place
- Ambitious yet practical: Set big goals, but stay grounded with disciplined execution and ruthless prioritization
- Direct yet kind: Never hold back from speaking your mind, but do so in a way that is kind to your colleagues
- Driven yet humble: Push for excellence and deliver fast, but keep your humility
What's In It For You?- Compensation: $100k-$150k base salary, depending on experience, expertise, and expected impact
- Ownership: Every full-time teammate receives Letter stock options, so you can share in the value you help create
- Benefits that have you covered: Comprehensive medical, dental, and vision coverage, plus a 401(k) with company match
- Benefits for the everyday: Company-supported commuter, connectivity, and wellness benefits, plus daily lunch in our Chicago and San Francisco offices
- Team events: Happy hours, dinners, events, and offsites with a team that genuinely enjoys spending time together
- Build with us: Join a fast-growing startup where you'll have meaningful ownership and impact, working closely with top-notch teammates to help build and scale Letter
