The Role
The People Operations Manager will establish and scale the People function, manage employee relations, engagement programs, performance management, payroll, and recruitment within a startup environment.
Summary Generated by Built In
People Operations Manager
Location: Chicago | Hybrid
About Letter AI
Letter 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 📈.
We’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.
- 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
- 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
- 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
- Oversee payroll in partnership with external providers
- Administer benefits programs (health, retirement, 401(k), etc.)
- Ensure compliance with payroll, tax, and benefits regulations
- 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
- Lead planning of company events (offsites, celebrations, team experiences)
- Coordinate internal events and engagement initiatives
- 5–7 years of experience across Human Resources/People Operations
- Strong generalist background across multiple HR functions
- 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
At 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
Skills Required
- 5-7 years of experience across Human Resources/People Operations
- Strong generalist background across multiple HR functions
- Experience in a high-growth startup or fast-paced, ambiguous environment
- Ability to build from scratch with limited infrastructure
- Self-starter with a bias toward action and ownership
Letter.AI Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Letter.AI and has not been reviewed or approved by Letter.AI.
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Equity Value & Accessibility — Job listings for early roles emphasize meaningful or significant equity alongside salary, indicating ownership is a core part of total compensation. References to early‑employee equity ranges suggest equity participation is accessible at foundational and senior levels.
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Retirement Support — A People/Operations role description includes administering benefits programs such as retirement and 401(k), indicating a retirement plan is in place. The presence of a 401(k) points to baseline retirement coverage rather than an ad‑hoc arrangement.
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The Company
What We Do
Letter AI is the world's first generative AI powered revenue enablement platform. Build and maintain all the collateral and training you need 10x faster with generative AI. Personalize instantly by vertical or individual customers using existing data. Ask questions in real-time to your own co-pilot with expertise in your data. Scale coaching with AI simulations, including screen sharing for demo practice. Supercharge your enablement efforts with Letter AI's unified revenue enablement platform. Reach out today to learn more.
