Recruiter

Letter AI, Inc.; Chicago (IL); Hybrid; USD 100,000 - 150,000; Full time

Benefits offered by this job

Stock options

Comprehensive benefits (medical, dent,

401(k) with company match

commuter, connectivity, and wellness

Job summary

Letter AI, Inc. is hiring its first dedicated Recruiter to accelerate growth and scale a ~60-person team in Chicago and beyond. You will own the recruiting engine, engage great candidates, run fast, high-touch processes, and partner with the People Ops Lead and hiring managers to improve how we hire.

You’ll source proactively, define ideal candidate profiles, and continuously optimize job postings, interview plans, and exercises while contributing to an exceptional candidate experience.

Qualifications

• 5+ years of recruiting experience, ideally in a fast-growing startup or high-velocity environment.
• Strong full-cycle recruiting across direct sourcing, screening, interview management, and closing.
• Strategic and hands-on; able to shape recruitment while handling last-minute changes.

Responsibilities

• Own recruiting end-to-end from inbound review to close.
• Coordinate high-volume, fast-moving interviews and ensure a great candidate experience.
• Partner with hiring managers to launch roles, define profiles, and improve postings and interview plans.
• Source exceptional candidates and optimize channels, boards, and tools.
• Establish high-signal interviewing practices with consistent questions and calibration.
• Improve TA tech stack and employer brand with the People Ops lead.

Skills

Full-cycle recruiting

Sourcing & outreach

Interview management

Stakeholder collaboration

Process optimization

Job description

View all jobs Recruiter Chicago People Hybrid Full-time

About Letter AI

Letter AI is the world’s first revenue enablement platform powered natively by AI. We’re reimagining the end-to-end revenue journey by turning real customer conversations and account data into actionable insights, personalized coaching, meeting prep, and next steps. Revenue teams aren’t asking for more content or tools. They’re asking for better outcomes. Letter does just that, empowering them to learn faster, sell smarter, and win more. We recently raised a $40M Series B and are already helping leading companies like Adobe, Lenovo, and Figma transform how their teams work. We 10xed our revenue last year and are looking for the best of the best in Chicago and the Bay Area to help us build on that momentum.

The Role

We’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 Operate

• 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