We’re only able to consider applicants based in the United States at this time. (You can work remotely anywhere in the United States. Once it is safe to do so, you’ll be welcome to work from our San Francisco office as well, if that is what you prefer.)

We're looking for an experienced leader to take our data pipeline & workflows to the next level. Archipelago uses a mix of Artificial Intelligence (AI) & humans-in-the-loop to turn unstructured information into structured data. Working closely with our Product & Engineering teams, as well as our in-house domain experts, you will take charge of our annotation / labeling pipeline with a focus on key metrics: quality, time, effort, and cost.

We’re a small team distributed around the world, with headquarters in San Francisco. We iterate quickly, build for the long term, and are looking for smart, independent folks who want to ply their trade with like-minded people.

The ideal candidate will be comfortable working collaboratively, across teams & timezones, and helping us define our platform culture. You’ll have significant impact, since the product & team is in its early stages. You’ll have a full team to support you, from research and design, through planning, development, deployment, delivery, and iteration.


  • Manage our annotation / labeling data pipeline & workflows.
  • Continuously evaluate & optimize performance metrics: quality, time, effort, cost.
  • Manage resource allocation between internal & external teams.
  • Work with our Product team and domain experts to make the pipeline more efficient.
  • Work with our Machine Learning (ML) team to automate parts of the pipeline.
  • Evaluate & Manage external vendors, including via RFPs/bake-offs. Navigate security audits & financial negotiations. Manage ongoing vendor performance.
  • Help recruit an internal team of annotators as needed.

Experience and Qualifications

  • 5+ years experience working for a startup (or tech company) as a Program Manager, Product Manager or Engineering Manager
  • 3+ years experience managing annotation pipelines
  • Some hands-on software development experience
  • 2+ years of remote work experience
  • You know how to communicate clearly no matter the medium: on Slack, task trackers, video calls, emails, in person, etc.


  • You’ll join at an early stage of the company, so you can take something from 0 to 1
  • We’re a supportive team who will give you as much assistance or independence as you like
  • We offer a full benefits package, including medical/vision/dental, 401(k), work-from-home budget, etc. — depending on location
  • Our headquarters are in San Francisco, but we’ve been a distributed company from the start.

About Archipelago

Archipelago is a Silicon Valley start-up working to change how risk is insured. Our platform enables large real estate owners, managers, brokers & insurance carriers to efficiently map their portfolio, manage their risks, and underwrite them, through a mix of machine learning and human intelligence. Our founders are tech & finance entrepreneurs with several IPOs and acquisitions under their belts. We are headquartered in San Francisco, have raised several rounds of VC funding, and currently employ over fifty people across the US & Europe.