Build the Future of AI Training
We're a fast-growing team on a mission to transform how companies train their people. Great benefits, meaningful work, and yes — a rooftop pickleball court.
"Best team I've ever worked with"
— What we hear from new hires after their first month
What We Believe In
Ship Fast, Learn Faster
We bias toward action. Launch, measure, iterate. Perfect is the enemy of shipped.
Customers Are Our North Star
Every decision starts with "How does this help our customers succeed?"
Radical Candor
We give honest feedback because we care. No passive-aggressive Slack messages here.
Own Your Domain
You're hired because you're an expert. We trust you to make decisions and run with them.
Win as a Team
No hero culture. We celebrate collaborative wins and support each other through challenges.
Have Fun
Life's too short for boring work. We work hard and play hard (see: rooftop pickleball).
More Than Just a Paycheck
We believe happy people do their best work. Here's how we take care of our team.
Rooftop Pickleball Court
Yes, really. We have a pickleball court on the roof. Weekly tournaments, beginner lessons, and Friday afternoon matches are a company tradition.
Top-Tier Compensation
Competitive salary, meaningful equity, and annual bonuses. We pay at the 90th percentile because we hire the best.
Unlimited PTO
Take the time you need. We track outcomes, not hours. Average employee takes 4-5 weeks per year (and we encourage it).
Remote-First + SF HQ
Work from anywhere in the US. Our SF office is available for those who want it, with monthly in-person gatherings.
Premium Healthcare
100% covered medical, dental, and vision for you and your dependents. Plus $500/year wellness stipend.
Parental Leave
16 weeks fully paid parental leave for all parents, regardless of gender. Plus $2,000 baby bonus.
Learning Budget
$3,000/year for courses, conferences, books, or anything that helps you grow. No approvals needed.
Dog-Friendly Office
Bring your pup to the office. We have treats, beds, and a dedicated "bark park" area on the terrace.
Team Retreats
Twice a year we bring everyone together somewhere amazing. Past trips: Costa Rica, Japan, Iceland.
Free Meals & Snacks
Catered lunch 3x/week at HQ, DoorDash credits for remote folks, and a snack wall that would make a bodega jealous.
Fitness Perks
On-site gym, ClassPass membership, and a running club that meets Wednesday mornings (optional caffeine stops).
Game Room
PS5, Nintendo Switch, foosball, and a vintage arcade cabinet. Perfect for afternoon brain breaks.
Join Our Growing Team
We're looking for exceptional people to help us build the future of AI-powered training.
Build the AI systems that power realistic, adaptive roleplay conversations. You'll work on prompt engineering, fine-tuning, voice synthesis integration, and developing our proprietary conversation scoring algorithms.
Requirements:
- 5+ years of software engineering experience
- Deep experience with LLMs (GPT-4, Claude, etc.)
- Experience with voice/speech ML (TTS, STT)
- Strong Python and TypeScript skills
- Passion for pushing the boundaries of AI
Craft beautiful, performant interfaces for our training platform. You'll own the entire frontend experience from the marketing site to the real-time voice conversation UI.
Requirements:
- 4+ years of frontend development experience
- Expert-level React and TypeScript
- Experience with Next.js and modern CSS
- Eye for design and UX excellence
- Experience with real-time/WebSocket applications a plus
Build the infrastructure that powers thousands of concurrent AI conversations. You'll work on our API layer, real-time systems, and integrations with enterprise customers.
Requirements:
- 3+ years of backend development experience
- Strong Node.js or Python experience
- Experience with PostgreSQL and Redis
- Understanding of WebSockets and real-time systems
- API design and documentation skills
Define the future of AI-powered training. You'll work closely with customers, analyze usage data, and drive the roadmap for our core platform and enterprise features.
Requirements:
- 4+ years of product management experience
- Experience with B2B SaaS products
- Strong analytical and data skills
- Excellent communication and stakeholder management
- Background in L&D, sales enablement, or EdTech a plus
Design intuitive, delightful experiences for AI-powered roleplay training. You'll own the end-to-end design process from research to high-fidelity prototypes.
Requirements:
- 3+ years of product design experience
- Strong portfolio showing B2B or consumer app work
- Proficiency in Figma and prototyping tools
- Experience with design systems
- Ability to conduct and synthesize user research
Enterprise Account Executive
SalesClose six and seven-figure deals with Fortune 500 companies. You'll run complex enterprise sales cycles, working with L&D leaders and sales executives.
Requirements:
- 5+ years of enterprise SaaS sales experience
- Track record of exceeding quota
- Experience selling to HR, L&D, or Sales Leadership
- Comfortable with complex, multi-stakeholder deals
- Experience with MEDDIC or similar frameworks
Be the trusted advisor for our enterprise customers. You'll drive adoption, identify expansion opportunities, and ensure customers achieve their training goals.
Requirements:
- 3+ years in customer success or account management
- Experience with enterprise B2B SaaS
- Strong presentation and communication skills
- Data-driven approach to customer health
- Background in L&D or sales enablement a plus
Be the technical expert in enterprise sales cycles. You'll run demos, architect custom solutions, and work with customers to integrate Roleplay Studio into their tech stack.
Requirements:
- 3+ years in solutions engineering or sales engineering
- Technical background (engineering or CS degree preferred)
- Excellent presentation and demo skills
- Experience with enterprise integrations (SSO, SCIM, APIs)
- Ability to translate technical concepts for business audiences
Build our content engine from the ground up. You'll create thought leadership content, case studies, and resources that establish Roleplay Studio as the leader in AI training.
Requirements:
- 3+ years in B2B content marketing
- Excellent writing and storytelling skills
- Experience with SEO and content strategy
- Ability to interview customers and create case studies
- Background in HR tech, sales enablement, or EdTech a plus
Build and scale our people function as we grow from 20 to 100+. You'll own recruiting, culture, compensation, and all things people.
Requirements:
- 7+ years in HR/People roles, with startup experience
- Experience scaling teams rapidly
- Strong recruiting and employer branding skills
- Data-driven approach to people decisions
- Passion for building exceptional culture
Shape our AI agents to be amazing training partners. You'll write prompts, evaluate AI conversations, build scenario libraries, and work with customers to create custom agents.
Requirements:
- 2+ years in instructional design, L&D, or sales training
- Strong writing and communication skills
- Curiosity about AI and prompt engineering
- Experience with roleplay-based training
- Background in sales or customer service a plus
Frequently Asked Questions
Common questions about working at Roleplay Studio
Don't See Your Perfect Role?
We're always looking for exceptional people. Send us your resume and tell us why you'd be a great fit.
Email us at careers@roleplaystudio.ai