People Operations Manager at Letter AI – Chicago, Illinois

People Operations Manager Location: Chicago | Hybrid
About Letter AILetter AI is the world's first unified revenue acceleration platform powered natively by generative AI. Our platform empowers sales teams at customers like Lenovo and Redpanda to ramp up faster with AI-powered training and coaching, instantly find and personalize collateral for customers, and engage their buyers with the industry's first AI Sales Room. We recently raised a $40M Series B led by Battery Ventures, with participation from existing investors including Y Combinator, Lightbank, Northwestern Mutual Future Ventures, Stage 2 Capital, and Formus. The round comes just four months after announcing our Series A, indicating a shift we're seeing in real time: revenue teams aren’t asking for more content or tools. They’re asking for better outcomes, and Letter AI is bringing those outcomes to life! We 10Xed our revenue last year and are looking for the best of the best in Chicago to join us on the adventure 📈.
The RoleWe’re hiring our first People Operations Manager, a hands-on, strategic builder who will establish and scale the People function from the ground up.This role will own all aspects of People Operations while partnering closely with leadership to support a growing organization (~40 employees and growing). You’ll work within Rippling (HRIS) and play a foundational role in building policies, systems, and culture. This role reports directly to the Founder & CEO of the organization.This is an ideal opportunity for a true HR generalist who thrives in fast-paced environments, takes initiative, and is excited to shape employee experience from day one.
What You’ll DoEmployee Relations

• Serve as a trusted advisor to employees and managers
• Address employee concerns, conduct investigations, and resolve workplace issues
• Ensure compliance with employment laws and company policies
• Build and maintain HR policies, procedures, and employee handbook

Employee Engagement & Talent Development

• Design and implement learning & development programs and career pathing
• Support managers with coaching, feedback, and team growth
• Drive initiatives that strengthen culture and employee engagement

Performance Management

• Build and manage performance review processes (goal setting, feedback cycles, evaluations)
• Partner with leadership on performance standards and KPIs
• Coach managers on performance conversations and improvement plans

Payroll & Benefits

• Oversee payroll in partnership with external providers
• Administer benefits programs (health, retirement, 401(k), etc.)
• Ensure compliance with payroll, tax, and benefits regulations

Recruitment & Vendor Management

• Partner with hiring managers on headcount planning and hiring strategies
• Manage external recruiting partnership and LinkedIn postings
• Build and elevate employer brand and candidate experience

Event Planning

• Lead planning of company events (offsites, celebrations, team experiences)
• Coordinate internal events and engagement initiatives

What You BringCore Experience

• 5–7 years of experience across Human Resources/People Operations
• Strong generalist background across multiple HR functions

Startup Mindset

• Experience in a high-growth startup or fast-paced, ambiguous environment
• Comfortable building from scratch with limited infrastructure
• Self-starter with a bias toward action and ownership

How We OperateAt Letter AI, we believe great companies are built by great people who show up authentically and operate with intention:

• Customer-Obsessed – Make customers unreasonably happy; everything else follows
• Ambitious, Yet Practical – Think big, execute with discipline and focus
• Direct, Yet Kind – Speak openly, communicate with respect
• Driven, Yet Humble – Move fast, deliver excellence, stay grounded

Why Join Us

• Build the HR function from the ground up
• Hyper-growth environment with real momentum
• Opportunity to shape culture, people strategy, and employee experience