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How to Actually Get Hired
Who reads applications, which channel gets a reply, and what they screen for.
Don't make these mistakes
Don't pitch generic 'AI for compliance' — Dili's edge is domain depth in construction/federal labor rules (Davis-Bacon, prevailing wage, certified payroll) plus deterministic enforcement, not just LLM extraction. Reliability matters because errors trigger large fines; don't wave that away.
What gets their attention
Naming specific rules (Davis-Bacon, prevailing-wage-and-apprenticeship, certified payroll) and understanding the AI-extraction-plus-deterministic-enforcement architecture shows real homework. Knowing the founders are ex-Coinbase (Chaturvedi also ex-Apple ML, KP Fellow) is a plus.
Why applying the normal way doesn't work
At <50 people, Dili has no recruiting team. Your application lands with a founder who is also running sales, product and payroll. The obstacle isn't a queue or an ATS, it's being seen at all. Cold outreach outperforms the form here, consistently.
Who to contact at Dili
Founding team
Chaturvedi co-founded Dili in 2023 (YC Summer 2023) after seeing that high-stakes audit and diligence work still ran through email and spreadsheets. He previously built products at Coinbase tied to more than $50M in revenue, did machine-learning research at Apple, and was a Kleiner Perkins Fellow.
Fernandez co-founded Dili and leads engineering. He previously led engineering projects for core retail infrastructure at Coinbase, where he worked with Chaturvedi. Detailed prior history beyond Coinbase/Dili is thinly documented publicly.
What to show them
Show you can build reliable document-extraction and rule-enforcement systems where accuracy is non-negotiable (errors = fines). Experience with structured/deterministic validation on top of LLM extraction, or regulatory/compliance data, is the edge.
A cold email that works at Dili
What Dili screens for
Screening signal: Naming specific rules (Davis-Bacon, prevailing-wage-and-apprenticeship, certified payroll) and understanding the AI-extraction-plus-deterministic-enforcement architecture shows real homework. Knowing the founders are ex-Coinbase (Chaturvedi also ex-Apple ML, KP Fellow) is a plus.
Customize your CV for the Dili role. Matching the job description language helps clear ATS filters.
Mistakes that kill applications
A recycled CV gets rejected fast at Dili (<50 people). They notice.
Skip 'I'm looking for...' — start with Khosla Ventures leading (Vinod Khosla publicly endorsed the real-time assurance layer), with strategic backing from Allianz and construction-focused Brick and Mortar Ventures, targets a specific, timely wedge and your specific angle on solving it.
The wait-and-hope strategy fails. Follow up on day five — response rates roughly double.
Frequently asked questions
How do I apply to Dili?
Through the roles on our Dili jobs page, or directly to a founder or department head if you can reach them. At <50 people, direct outreach outperforms the form.
Does Dili respond to cold emails?
Response rate data for Dili not yet confirmed.
Who is the hiring manager at Dili?
At this size, hiring is usually run by a founder or department head.
How competitive is it to get hired at Dili?
Expect 50-100 applicants in the first two weeks for B2B, Finance and Accounting roles at this size. Apply within 72 hours for best odds.
Have your application sent for you
We spot Dili-type roles within 48 hours and get your tailored application in before the crowd.
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