About Prodigal
What is Prodigal?
Prodigal (Prodigal Technologies Inc.) builds AI agents and software for loan servicing and debt collections. Its Y Combinator profile says "We build AI agents for loan servicing and collections", and its adverts say it works with "100+ financial institutions across North America": lenders, loan servicers and debt collection agencies. The product line on its site covers an AI agent for collections operations (proAgent), a payment portal (proPay), QA automation and scorecards (proInsight), real-time automated notes (proNotes) and dynamic prompts for real-time agent assistance (proAssist). Prodigal sells software to the businesses that lend and collect; its live adverts are for engineering, AI deployment, customer success, analytics, sales, marketing and people-operations roles. The company says it was founded in 2018 in Mountain View, California, backed by Y Combinator, and it raised a Series A from Accel and Menlo Ventures in 2021. Y Combinator's company page lists a team size of 99 (read on 7 November 2026).
Where will I work?
The address in the website footer is 655 Castro Street, Suite 2, Mountain View, California 94041, and Y Combinator's profile says the company is "Headquartered in Mountain View, California". Most of the open roles are in India, though: on 7 November 2026, 13 of the 14 live adverts were in Mumbai (7) or Bengaluru (6), and one, an Account Executive, in Mountain View. Where the India adverts state a work mode, it is the office: six of the 13 do (the other seven say nothing), with wording such as "Mode of work - 5 days in office", "Mode of Work - In-Office (Koramangala,Bengaluru)" and, for Customer Success in Mumbai, "Based out of our Mumbai office, 5 days a week". The Mountain View sales role is hybrid: the advert asks for someone located about an hour's drive from Mountain View "so we can meet in person 3-5 times a week". Some roles serve North American customers: the Customer Success Manager advert asks for availability "during US business hours (until 4:30 PM ET)", and the Strategy and Operations Analyst advert mentions periodic travel to the US.
What is the Prodigal team like?
The careers page names five values: curious optimism, bias for action, pursue excellence, specificity and radical candor. It promises intellectual freedom, with staff "empowered to create change without going through endless bureaucracy" and "transparent, merit-based decision making within the team". It describes leadership mentoring through lunches and 1:1 chats, an open culture that encourages exploring other verticals and side projects, sponsored learning, and tools such as Cursor, Devin.ai, TrueFoundry and Databricks. The team meets for offsites twice a year (the page shows Goa and Mulshi Hillstation), with regular team lunches, cooking challenges and outings, and the adverts mention football and table tennis. The Strategy and Operations adverts say team members have come from BCG, Deloitte, EY, Blackstone, Meta and Amazon. Two of the 14 live roles are internships, in content marketing and people operations.
Work-Life Balance
Prodigal's careers page lists a flexible schedule among its perks: "Morning person? Start work while the world's still sleeping. Night owl? Ramp things up while others are winding down." It adds that staff are "fully trusted to create the right conditions for your own personal peak productivity" and asks only that they "be available to your teammates for seamless collaboration". No core-hours window is published. Six of the 14 live adverts on 7 November 2026, for Customer Success, Analytics and Data Science and Machine Learning roles in Mumbai and Bengaluru, list a flexible schedule among their perks. Expect the office rather than home: six of the 13 India adverts state a work mode and all say in-office (two say five days a week; three of the six also list a flexible schedule), and the Mumbai Customer Success Manager role also asks for availability during US business hours. The page also lists an unlimited vacation policy: "Our unlimited vacation policy empowers you to take the time you need to recharge and pursue your passions." It publishes no day count, so ask how much leave people actually take.
Perks and Benefits
- Flexible schedule: early or late starts, with availability to teammates expected
- Unlimited vacation (paid time off); no day count or public-holiday terms are published
- Health insurance for you and your family, per the careers page
- Heavily discounted Cult Gym memberships; the adverts also mention a gym membership
- Allowances for food, travel and electronics; the adverts add meals at the office
- Sponsored courses, books and conferences, plus GenAI and AWS credits for hackathons
- Mentoring from the leadership team, and an open culture that encourages exploring other verticals through side projects
- Team offsites twice a year, regular team lunches, cooking challenges and outings
- Access to current AI tooling, including Cursor, Devin.ai, TrueFoundry and Databricks
- Account Executive advert (Mountain View): pay range of $200k-$280k OTE plus ESOPs