Jobs at Promptless
Work at Promptless!
Section titled “Work at Promptless!”Promptless builds AI agents that automatically update customer-facing documentation. Some of the best docs teams use Promptless, and we serve startups and Fortune 500 companies alike. We were funded by Y Combinator and raised a seed round from top VCs and angel investors.
We’re a small team in San Francisco where everyone works directly on the hardest problems at the company. On any given day, you might talk to a customer, design a feature with the founders, ship code, and watch real users interact with what you built. We believe AI won’t take people’s jobs—but people who use AI well will replace those who don’t. We’re building the tools to make AI better fit into the workflows for people at work.
Read more about why we’re building Promptless.
If you want to do the most impactful work of your career at a company that’s growing fast, we’d love to hear from you.
We’re hiring for:
- Founding Docs Practice Lead: Own the documentation discipline at Promptless. Work directly with customers to onboard them, build the playbook, and coach teams on AI-assisted docs.
- Founding Engineer: Build the core product—AI agents, integrations, and infrastructure that powers automatic documentation updates.
For all roles, reach out at founders@gopromptless.ai.
Founding Docs Practice Lead
Section titled “Founding Docs Practice Lead”San Francisco, CA · Full-time
This is a one-of-one role. You’ll own the documentation practice at Promptless—working directly with customers to onboard them onto the platform, building the methodology for AI-assisted documentation, and growing our reputation as the company that makes documentation teams more effective. Think of it like a practice lead at a top consulting firm, except the domain is docs and the leverage is AI.
What you’ll do
- Onboard customers onto Promptless, working hands-on with their documentation, codebase, and team workflows
- Coach technical writers and other documentarians on structuring documentation, using AI effectively, and getting the most out of Promptless
- Build and refine the playbook for how documentation teams adopt AI-assisted workflows
- Shape the product by translating real documentation workflows into features
- Champion the documentation community—share what’s working, surface new roles emerging from AI adoption, and help teams thrive
What we’re looking for
- Deep experience in technical documentation—you’ve written developer docs, API references, or support content
- Comfortable with code—you can read a PR and understand what changed (maybe with Claude’s help)
- Excited about AI and eager to push the boundaries of what’s possible with LLM-assisted writing
- Strong communicator who can earn trust with both engineers and writers
- Entrepreneurial mindset—you’ll be building this function from scratch
Compensation: $140k–$200k base + 0.25%–1.00% equity, depending on candidate level.
Interested? Reach out at founders@gopromptless.ai.
Founding Engineer
Section titled “Founding Engineer”San Francisco, CA · Full-time
You’ll build the core product—the AI agents, the integrations, the infrastructure that powers automatic documentation updates for hundreds of companies.
What you’ll do
- Ship production code that real users depend on
- Build across the full stack—React frontend, Python/Flask backend, API integrations, and Kubernetes infrastructure
- Work with LLMs to build agent-based systems
- Talk to customers and translate their needs into product
What we’re looking for
- You’ve shipped production code for real users
- You’re comfortable across the stack—frontend, backend, infra
- You’ve built something with LLMs (work projects or side projects both count)
- You learn fast and experiment constantly
Bonus: Experience building LLM agents or contributions to open-source AI projects.
Compensation: $140k–$200k base + 0.40%–2.00% equity, depending on candidate level.
Interested? Reach out at founders@gopromptless.ai.