Interviewing Arthur Willson | Proptech Operator & Investor

Welcome back to Welty’s Words’ Interview Series!

I’ve been quite busy with work and other life priorities (moving soon), but I am excited to share with you all a conversation I had with my friend Arthur. If you are interested in what it’s like to start your early career in tech and continuing to grow, then you’ll particularly enjoy this.

I’ll be putting out a more traditional piece soon!

Enjoy!
- Welty

Today’s Guest

Arthur Willson is a friend and fellow Wake Forest grad who has long been involved in the technology, entrepreneurial, and investing space. He joined a startup, Till, at the pre-seed stage through acquisition, where he now is a product manager. Additionally, he is a founder of a trademark monitoring firm and is a venture partner at NextGen Venture Partners. We discuss taking an untraditional path into tech coming out of our school, as well as what it takes to grow into various roles across the stages of building a startup. Let’s get into it!

The below responses have been paraphrased for clarity and ease of reading.

What was it like wanting to work in Tech in undergrad?

Honestly, it was a bit difficult. As you know, our business school programs were very focused on student outcomes, but only if they resulted in a finance or consulting job. I had to really advocate for my early role at Till to be accepted by the school, but it was absolutely worth the effort. There’s a lot of strong academic talent that would excel in other industries at Wake, and I hope that is becoming increasingly accepted. I did very quickly learn the importance of conviction in my direction, which has proven valuable in my career so far.

How did you join Till?

While there may have been difficulty convincing the Wake business school of the value of working at Till, I did actually meet our founder David Sullivan at a WFU Entrepreneurship event (separate from Wake’s business school). He was an older WFU grad and I immediately connected with his mission of improving financial access to housing through flexible rent. I took the plunge, moved up to Washington D.C., and we got to work.

What roles did you have at Till? What core skills helped you the most?

I started as a sales development representative, then briefly worked on the product, before spending the majority of my time leading partnership success. The hardest challenge in the early days was prioritizing the most important issues. When you’re a small company, there are always things competing for your attention. From a business perspective, I ultimately learned that focusing on the customer quickly became our number one priority. Learning this early on set me up for success in leading our customer success motion and my current product role.

Out of necessity, as an individual, I quickly learned to address any issue at hand by becoming comfortable quickly researching and asking the right questions to get me up to speed. Joining an early stage company requires nimble thinking. I think this is the most important skill for succeeding in a startup environment. Early stage companies are naturally fast moving and volatile, so being comfortable operating in a fast changing environment set me up for success.

With Till now being acquired, what was it like transitioning to the new organization? What was the biggest success factor in the integration?

Well, it helps that we were genuinely excited to be joining the Best Egg team. Our leadership team at Till spent considerable time before the deal closed making sure that our teams were a cultural fit. This is a critical factor in whether or not an acquisition will be a success. Otherwise, speed of development can plateau, Go-To-Market teams can’t work together, and things fall apart.

Aside from the company transition, I understand you’ve also transitioned to Product Management. What is helping you succeed in the new role?

I’m not the most technical guy by nature. Writing code is not my passion, but the ability to read technical documents and understand the translation layer between business and technical requirements is vital. I also focus on building genuine relationships with the engineers I work with, since without them, the work of a Product Manager is futile.

My deep history working with the legacy Till product, and my customer facing roles has set me up for success in defining the product vision. Customer empathy and knowing the existing limitations of our product help me think through what’s next. Just how strong relationships with your engineering are essential, so is understanding the true desires of your customers and how they could work in the product.

What is your biggest piece of advice for someone looking to work in tech?

Build strong personal relationships, and don’t be afraid to dig into something that you’re unfamiliar with. This industry moves faster than many and, especially if you intend to be at a startup, you’ll need to work cross-functionally. If you are genuine, people are more than willing to help you learn what you need to succeed. Remember that an opportunity to constantly grow your skill and mindset is a great spot to be in, and you’ll do just fine.

Want to connect with Arthur? Reach out to him on LinkedIn!

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