Exploring Tech Tools, Culture, and AI with the CTO

Dive into our Q&A with Brian Moseley, Co-Founder and CTO at Sixfold. We're chatting about his tech journey, from the early days at Sega to his recent tenure at American Express, and what led him to Sixfold. Brian also shares insights into the team's 'chill, pragmatic, and adaptable' culture and talks about his passion for Warhorn, his own gaming community project.

What’s your career path and how did it lead you to becoming Sixfold's CTO?

My software career began in college when I joined my friend’s community and media startup; we were among the first to experiment with web-based advertising. Through this venture, I met many tech professionals in San Francisco, who got me excited about the emerging web scene there. Ultimately, I decided to leave school and move across the country to work at Sega of America, focusing on database administration for their website.

From there, I joined several early-stage startups, including Critical Path, where I was the 17th employee. I experienced growth through its IPO, becoming an engineering manager and software architect. Later, I worked at the Open Source Applications Foundation, implementing a number of obscure internet protocols as the lead of an open source calendaring server.

As my career progressed, I found myself being the first engineering hire at a startup and then the first employee of another, so the logical next step was to become a cofounder and the CTO of Hoodline, a hyperlocal journalism company. Unfortunately, we did not succeed in reinventing local news, so I decided to try my hand at a big company and started working for American Express. 

I made the leap to full-time engineering management at Amex and eventually spent five years as the firm’s Head of Developer Experience, serving a global crew of 10,000 software engineers. Working in a big company was an incredibly educational part of my career, but I increasingly had the itch to build something from scratch again. So, Alex’s pitch got my attention and ultimately led to me cofounding Sixfold AI.

What originally attracted you to Sixfold?

It was a combination of three things:

1️⃣ I’d been looking for some time for an opportunity to build a company, team, and product from scratch.

2️⃣ I had a great time working with Alex briefly back in the early 2000s, so the prospect of cofounding with him was super appealing.

3️⃣ It seemed like exactly the right moment to go after the opportunities unlocked by generative AI in vertical business domains. Everything I saw was focused on LLM infrastructure and tooling, but nobody was talking in public about using generative AI to solve problems for business users like insurance underwriters.‍

‍How is Sixfold different from other players in the field?

We aren’t encumbered with legacy technology, organizations, or ways of working. We’re building our team and product from the ground up, which means we get to experiment freely and iterate quickly.

Another aspect that sets us apart is our commitment to ensuring our product is something users look forward to, not something they complain about with each use. The complexity and challenging nature of many enterprise software interfaces can be daunting. That's why we focus on user-friendliness and intuitive design.

We value user delight! Sixfold is not only effective; it's also fun to use.

What aspects of Sixfold and its technology are you most passionate about and find particularly exciting?

I love all of my children equally 🙃
‍
That said, as you might expect, I’m engrossed in the rapidly developing craft of generative AI engineering. What we’re doing goes way beyond basic “chat with your document” scenarios. We have a whole new set of primitives to assemble into complex systems - and they are evolving so fast it’s hard to keep up! It’s particularly interesting to apply these techniques in near real time as part of the live user experience. 

Our AI pipelines are hybrids of batch and streaming, with the work distribution and scheduling needs of batch processing and the resiliency and throughput of a real-time system. “Notebook AI” solutions don’t scale or meet our availability and performance requirements without a lot of additional engineering.‍

How would you characterize the dynamic and strengths of the team?

‍Our founding team has so much experience starting and scaling companies, we’ve all done zero to one many times. That doesn’t mean we don’t make mistakes, but they tend to be new mistakes, not many of the ones we’ve seen before. And my co-founders are teaching me everything there is to know about insurance.

The core of our tech team is a group of veteran startup hands with deep experience in their functional areas who can all flex into team building and leadership as we grow. We built on this core with a group of 'smart and gets things done' engineers who can build fast and iterate quickly, especially the closer they get to the AI layer of our stack.

Ultimately, our tech team is able to build, test, and learn quickly while keeping the quality bar high. And our go-to-market team keeps us oriented, fusing an understanding of what our customers need with a compelling vision for the future of underwriting.

How do you contribute to the team's growth and development?

As a hands-on-keyboard software engineer for nearly 30 years, I lead our product and platform development from the front. I pair with our engineers to help them develop their core software skills, which include architecture, design, coding, troubleshooting, and operating in production. This also provides an opportunity for them to build mentorship skills, as there is much I can learn from them as well.

I strive to create opportunities for our team members to step outside their comfort zones. Most of our engineers arrived with a specialization in some technical area, whether it be front-end development, infrastructure, or AI. However, our team is most effective when any member can work on any feature, regardless of where it falls in our stack. Therefore, I encourage each engineer to become proficient in all our languages and frameworks. For example, an AI engineer might make changes to our core domain model in Ruby, or a front-end engineer could add a new step to our AI pipeline using Python.

What is an achievement you are particularly proud of that the team has accomplished since the launch?

I’m most proud that we’ve been able to make the product work the way we envisioned it. It’s not just about our accuracy, which is great and getting even better. Remember the first time you experienced the magic of ChatGPT? Underwriters have that same feeling when they use Sixfold AI. They don’t have to read a hundred pages of tedious documents anymore just to find the three hidden nuggets that show the risk in an insurance case. They can sit back and let Sixfold find the nuggets for them in a matter of minutes. Magic!

In three words, how would you describe the team's culture?

Chill. I don’t mean we’re not working hard or that we don’t have high intensity about our venture. But you can tell that most of us have been in startups before because people handle the pressure really well. Nobody’s freaking out or creating negative vibes. We all have each others’ backs.
‍
Pragmatic. We aren’t striving for the perfect user experience or the most scalable systems right out of the gate. We’ll get there over time as we prove our right to be in business by delivering things customers want to pay for. We push ourselves to make “two-way door” decisions a little bit faster knowing that we can always iterate or reverse course later.

Adaptable. We develop in quick sprints and frequently stop to check in on what’s most important right now. Some weeks, that’s building features. Others, it’s improving resilience or shoring up security. At this stage of the company, every next customer engagement brings new problem statements and requirements. While we’ve introduced a measure of longer-term planning, we’re still keeping our heads on a swivel (as my high school football coach would say) to make sure our vision, roadmap, and near-term development plans evolve in the face of constant market discoveries.

How do you stay updated with the advancement in AI and LLMs, any particular newsletters or blogs that you like to follow?

I read 'Ben's Bites' daily, a resource recommended by Alex (our CEO) when I first joined. It's even included in our welcome email to all new team members. In addition, I follow 'The Information', particularly their newsletter 'AI Agenda', which I find very insightful and full of links to deeper reading.

Our team is also a significant source of discovery. Team members are constantly tuned into various niches and aspects of our industry, sharing relevant links and resources in Slack. We’re reading each other's stuff all the time.

Could you share some of your favorite tech tools or frameworks that you rely on heavily?

iTerm and Visual StudioCode - This is where I write and run my code. Others love their all-in-one commercial IDEs, but I do just fine with these tools.

Ruby and Rails - I’ve been building Rails apps and writing scripts and command line tools in Ruby since 2007. It just keeps getting better! I spend a lot of time with JavaScript as well, and it’s fine, you can’t really get away from it in the modern world, but I’ll always reach for Ruby when I can.

React - Again, I have been doing it since near the beginning, and it still scratches the itch. Haven’t had any reason to embrace the Hotwire part of the Rails omakase experience or to dabble in any of the post-React web frameworks. Maybe somebody out there will finally make me see the light?

Linear - Modern project management for product development that strikes an almost-perfect balance between the “all batteries in the universe included” and “bring your own batteries” approaches of pretty much everything else out there.

Mermaid - Being able to create a diagram by writing code has 10 x'ed my output of diagrams, which improves the clarity of my engineering dialogues.

Do you have a favorite AI solution that you would like to highlight?

Not yet! The gen AI ecosystem is still immature and changing rapidly. The popular tools and frameworks don’t always prioritize qualities we require for production usage - stable APIs, for example, or the ability to bring your own observability tools or work distribution systems. We’re having a better experience stripping down to the basics and devising our own abstractions over AI primitives (model and vector store APIs, for example) and in-house utilities.
‍
Ask me again in 12 months - I may well have a different answer!

Any fun tech projects that you're working on at the moment (non-Sixfold-related)? 

Yeah, there are two main things I'm focusing on outside of work. Firstly, I've recently picked up World of Warcraft again after about a year's break. It's been a fun way to spend time outside of building our company.

More to the point, I started a website back in 2001 called Warhorn, which I'm still running today, more than 20 years later. It's essentially a marketplace for tabletop role-playing games, board games, collectible card games, miniatures, word games, and more. I originally created it out of my love for tabletop role-playing, particularly tournament-style games like Dungeons and Dragons. It was born from the need to streamline the logistics, scheduling, and signups for large gaming events. 

The site was initially written in PHP in 2001, then I rewrote it in Ruby on Rails in 2011 and added a React front end around 2016 or 2017. Warhorn has been my laboratory for learning new technologies, such as GraphQL. It's a SaaS offering, which has helped me familiarize myself with various cloud providers and vendor systems. This experience has directly influenced my decisions at Sixfold and at previous jobs.

Warhorn is not just my tech lab but also my way of contributing to the gaming community. It's a long-standing project with over 25,000 monthly active users. I've kept it running as a passion project, not for commercial purposes. It's a creative outlet for me, similar to painting on canvas. It's an enjoyable aspect of my life where my profession and hobby intersect, providing a way to relax and be creative.

Warhorn seems absolutely awesome! Thanks, Brian, this was a lot of fun. 

‍

Are you excited about the opportunity to work at Sixfold?

If you’d like an opportunity to work with us, check out our vacancies.