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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 yourself as someone who finds compliance interesting as a category. Arik has been working in compliance infrastructure for a decade and has very specific views on what the actual problems are. Generic enthusiasm for 'regtech' or 'fintech compliance' will not land. Lead with what you know about the specific buyer, the head of compliance at a hedge fund, the general counsel at a private equity firm, the operations lead at a family office, or with a technical proof of work that demonstrates you can build the document processing and risk scoring infrastructure. If you have direct experience on the buy side of this process (having been a compliance officer or operations lead at an investment firm), say so immediately. That experience is worth more than any technical credential here.
What gets their attention
Steward raised $5M on March 18 with two founders and clients already managing over $100 billion in assets across their platform. No careers page. No job listings anywhere. Founded in 2025. Arik Oslerne stated in the funding announcement that managing AML compliance "has long scaled in a linear way: firms can't keep up with growing workloads using existing resources, leading to repeated remediation cycles and increasing regulatory pressure." That framing signals an enterprise sales motion: Steward is going upmarket, targeting institutions with complex compliance burdens. Upmarket enterprise sales requires people who can speak the buyer's language, manage enterprise procurement cycles, and build trust with compliance officers who are professionally risk-averse. That infrastructure does not exist yet at a two-person company. Motive Partners' investment history is a strong signal for which hires come next. Motive backs financial infrastructure companies that become operating systems for regulated industries. Their portfolio companies at this stage typically build out three functions in parallel: enterprise sales and customer success, compliance domain expertise (to maintain regulatory credibility), and product engineering (to expand coverage across jurisdictions and investor types). All three of those functions are currently handled by two people at Steward.
Why applying the normal way doesn't work
There's an ATS, but at Steward, referrals get priority. Your cold application competes with sourced candidates and internal recommendations.
Who to contact at Steward
What to show them
Steward's product must stay current with AML/KYC regulations across at least three major jurisdictions simultaneously. As they expand to new markets and add new investor types, someone needs to translate regulatory requirements into product decisions: what data needs to be collected, what checks need to run, what documentation is required. This role sits at the intersection of compliance knowledge and product thinking, and it does not exist yet at Steward. Core skills: AML/KYC regulatory frameworks (FATF, UK FCA, EU AMLD, US FinCEN), investment fund compliance, product management, ability to write clear regulatory product specs, experience in fintech or financial services compliance Proof of work: Write a two-page product spec for how Steward should handle a specific complex investor type: a family office with beneficial owners across three jurisdictions, one of which is an offshore holding company. What documents would you require, what checks would you run, what risk signals would you flag, and what human escalation logic would you build? This demonstrates you understand both the compliance problem and the product design challenge.
A cold email that works at Steward
What Steward screens for
Steward raised $5M on March 18 with two founders and clients already managing over $100 billion in assets across their platform. No careers page. No job listings anywhere. Founded in 2025. Arik Oslerne stated in the funding announcement that managing AML compliance "has long scaled in a linear way: firms can't keep up with growing workloads using existing resources, leading to repeated remediation cycles and increasing regulatory pressure." That framing signals an enterprise sales motion: Steward is going upmarket, targeting institutions with complex compliance burdens. Upmarket enterprise sales requires people who can speak the buyer's language, manage enterprise procurement cycles, and build trust with compliance officers who are professionally risk-averse. That infrastructure does not exist yet at a two-person company. Motive Partners' investment history is a strong signal for which hires come next. Motive backs financial infrastructure companies that become operating systems for regulated industries. Their portfolio companies at this stage typically build out three functions in parallel: enterprise sales and customer success, compliance domain expertise (to maintain regulatory credibility), and product engineering (to expand coverage across jurisdictions and investor types). All three of those functions are currently handled by two people at Steward.
Customize your CV for the Steward role. Matching the job description language helps clear ATS filters.
Mistakes that kill applications
A recycled CV gets rejected fast at Steward ( people). They notice.
Don't open with what you want. Open with what Steward is dealing with right now — AML and KYC compliance has been stuck in spreadsheets and email threads for decades, and what you'd do about it.
The wait-and-hope strategy fails. Follow up on day five — response rates roughly double.
Frequently asked questions
How do I apply to Steward?
Through the roles on our Steward jobs page, or directly to the hiring manager if you can reach them. At null people, direct outreach outperforms the form.
Does Steward respond to cold emails?
Response rate data for Steward not yet confirmed.
Who is the hiring manager at Steward?
At this size, hiring is usually run by the hiring manager.
How competitive is it to get hired at Steward?
Typical applicant count for AI roles ( people): 100-250 in two weeks. Apply fast.
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