Why we invested in Steward

We’re excited to announce our investment in Steward, the AI-first AML Compliance platform, as part of its $5m pre-seed round led by Motive Ventures.

At Outward, we are constantly seeking exceptional founders building technology to solve deeply entrenched problems within financial services and connected sectors. Problems that everyone recognises, yet few have successfully addressed. Steward represents this ambition perfectly.

The investment also marks a proud moment in our eight-year history as a firm: the first time we have backed a repeat Outward founder. I wanted to share a few personal anecdotes to shed light on how we reached this moment and why we are so bullish for the journey ahead.

Between 2017 and 2019, an initial founding team of four, including myself, set out to raise Outward’s maiden fund.

The experience of setting up this fund and working with traditional (archaic) administrators, ultimately led us to our investment in Vauban. I have written previously about both our investment in Vauban and its journey to exit so I won’t revisit that story here. What matters for this one is that it is where I had the great pleasure of working with Arik, now CEO and co-founder of Steward.

A second notable experience in the course of setting up our fund was managing the onboarding process of our 60+ LPs, particularly around KYC and AML requirements. To this day I still carry mild PTSD from it.

Investor onboarding packs are messy by nature: unstructured documents, corporate registries, trust structures and foreign-language filings. Reviewing them requires expertise and judgement, and almost always triggers follow-up requests to verify the source of wealth and ultimate beneficial ownership.

The result is a slow, frustrating process with constant back-and-forth between compliance teams and clients. Onboarding timelines can stretch from hours into days or even weeks per investor.

This, of course, is not just an Outward VC issue. The problem exists across the entire spectrum of regulated financial services, but is particularly acute in the world of investment management, private wealth and private banking, where ownership structures are often complex and cross-border.

If you were to measure NPS across the client lifecycle, this part of the client experience would almost certainly sit right at the bottom.

Until recently, this complexity made compliance automation almost impossible. Advances in AI, particularly in document understanding and agentic workflows, are now making it feasible to automate large parts of compliance operations for the first time.

Steward is building an end-to-end, AI-first platform for automated onboarding and ongoing AML compliance.

The ambition is simple but transformative: reduce onboarding timelines from days or weeks to minutes.

Rather than forcing compliance teams to stitch together multiple tools and manual processes, Steward brings the entire workflow into a single system powered by AI agents that replace the work of a seasoned KYC analyst. They review documents, extract relevant data, identify beneficial owners and directors, screen sanctions and adverse media, and evaluate findings against configurable risk frameworks across jurisdictions and languages.

From the end client perspective, the goal is clear: zero friction.

Want to send across your ready-made KYC pack of PDF documents? No problem. Bulk upload the documents and Steward’s agents will do the rest.

The result: day-zero onboarding in up to 80% of cases.

Steward’s initial focus is the investment management and services ecosystem, where onboarding complexity is particularly acute and automation has historically been more challenging to achieve. By targeting this segment first, Steward is tackling one of the hardest corners of compliance, and one where the value of solving the problem is immediately clear.

In many ways, this investment has been years in the making.

Beyond first-hand experience of the pain, we had the good fortune of working closely with one half of the Steward super duo through our investment in Vauban in 2021. That year was a phenomenal journey and one that had a profound impact on my own career. It set a benchmark for decisive leadership, exceptional hiring and product excellence.

Arik, Vauban’s former COO and widely recognised as its third co-founder, played a pivotal role in the company’s success. He combines a relentless work ethic with extremely high standards and leads by example.

What always stuck with me, however, was his calm in moments of crisis. These moments, of which there were plenty, would typically end up with Arik and myself in a room with a whiteboard. I got to see what he was truly made of in those moments, right up until the company’s sale to Carta in 2022.

On the day the company agreed to be acquired, I gave each Vauban founder my word that if they decided to build another business, whether together or individually, we would jump at the chance to back them again.

Three years later, Arik told me he was ready to go again, tackling a problem he had lived and breathed for much of his career and partnering with one of the most exceptional technical builders he has ever met.

Moshe, Steward’s co-founder and CTO, was a founding engineer at two of Israel’s most successful consumer tech companies, Fiverr and Lemonade. His experience places him among the strongest technical founders we have worked with, and his passion for building elegant, eye-catching products for “boring” industries is infectious.

Together, Arik and Moshe bring a rare combination of deep domain expertise and world-class engineering capability, precisely what is required to tackle a technically and operationally complex challenge like compliance automation.

Fair to say, we stuck to our word and jumped at the chance!

At Outward, we believe one of the most profound impacts of AI will be the transformation of knowledge work within regulated industries.

Compliance is a prime example.

For decades, compliance teams have scaled linearly with the growth of financial institutions. More clients meant more analysts, more manual processes and ever-increasing operational costs. It is one of the largest operational cost centres across financial services.

Platforms like Steward introduce true operational leverage. Instead of scaling compliance teams in proportion to client growth, institutions can oversee automated systems capable of completing most workflows faster and with greater accuracy.

If Steward succeeds in executing on this vision, it has the potential to fundamentally reshape how compliance functions operate across financial services.

This is a future we’re excited to help build, and one we are especially proud to pursue alongside founders we know and trust as friends.