Jun 3, 2026 · 11:45 PM
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Why a Legal Tech Startup Is Interviewing Candidates on Sundays

As AI inflates resumes, startups like Crosby are turning to live work trials to vet candidates. The company interviews on Sundays to accommodate employed applicants who can't take time off.

Judith Murphy
· 4 min read · 104 views

A legal-tech startup is scheduling interviews on Sundays, not as a pressure test, but to accommodate candidates who cannot take time off for the booming trend of job auditions.

Ryan Daniels, founder of Crosby, a startup-law-firm-hybrid providing legal services to other startups, started asking candidates to come in on Sundays and expected some eye rolls. Instead, he found that many applicants were relieved. A weekend interview meant they did not have to burn a vacation day or lie to their current boss just to stay in the running for a new job.

This scheduling shift is a direct response to a rapidly spreading hiring practice: the work trial. As artificial intelligence makes it increasingly simple to inflate a resume with generated content, employers are losing confidence in traditional interviews and portfolios. Companies now want to see people actually do the work before making an offer. At Crosby, this means a software engineer is dropped into a live project to demonstrate how they code and how effectively they use AI coding assistants on the job. For business roles, candidates face panel interviews with the executive team.

While asking someone to prove their skills sounds highly practical, it extracts a heavy logistical toll on the applicant. Work trials often require hours of focused effort, sometimes over multiple days. Foxglove, a startup building data and monitoring software for robotics, utilizes paid work trials that can consume entire weekends. Ellis Neder, now the head of design at Foxglove, previously took days off and flew to the company's San Francisco office for a trial over a long weekend just to secure the role.

For employed professionals looking to switch companies, taking a Tuesday morning off for a three-hour live audition is incredibly risky. It raises suspicion from their current managers and drains their limited paid time off. Crosby's Sunday solution cleverly removes this friction. It also works well for the startup internally. Daniels noted that his executive team is often working on Sundays anyway, but their calendars are less clogged with routine meetings, giving them more quality time to actually evaluate a candidate.

Testing for Substance Over Presentation

This movement toward live auditions fundamentally changes what it means to be a strong candidate. Polish and presentation are taking a backseat to demonstrated competence under pressure. Harvey, a major competitor in the legal tech space valued at $11 billion, has also adjusted its methods to account for the superficiality of modern credentials. Winston Weinberg, Harvey's CEO, recently told the Access podcast that the company often has candidates go back and forth on a problem set in a shared Google Doc. Weinberg observed that candidates who excel at presenting themselves often break down when forced to write out direct, analytical responses to complex problems in real time.

At Crosby, the audition intentionally bleeds past the formal technical assessment. Candidates join the team for lunch or dinner, which gives them a transparent window into the daily culture and helps close the deal for the right talent. Daniels told Business Insider that this extended, unstructured interaction is a critical closing tool. If people genuinely vibe with the team, they never lose them to competing offers. If the chemistry is not there, it serves as a valuable lesson for everyone involved.

The broader implication for the hiring market is a growing divide in how talent is evaluated and compensated. Startups are willing to pay for your time during a trial phase, but they demand tangible proof of output upfront. Candidates will increasingly need to weigh the cost of participating in these auditions against the potential payoff. As work trials become a standard fixture in the tech and startup hiring landscape, expect more companies to experiment with off-hours scheduling to accommodate the reality that the best talent is almost always already employed.

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Judith Murphy is a financial journalist and market analyst covering AI, technology stocks, and emerging market trends. She has contributed to multiple financial publications and brings a data-driven approach to her coverage of the technology sector and its impact on global markets.
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