Suggestions
Steve Brain
Head of Technical Product & Portfolio CTO/EVP
Professional Background
Steve Brain is a distinguished technology leader and software engineer with an extensive career focused on building and managing software organizations that deliver exceptional customer value. With a wealth of experience that spans over several pioneering industries, including financial services, e-commerce, and B2B SaaS (Software as a Service), Steve has a proven track record of creating market-leading software solutions. His career trajectory has taken him from developing real-time trading systems to architecting large-scale e-commerce applications, and optimizing supply chain processes. He has successfully led engineering organizations across the United States and Europe, showcasing his versatile leadership style and ability to foster thriving teams.
In his most recent position, Steve serves as the Head of Technical Product and Portfolio CTO/EVP at Trilogy, where he plays a vital role in shaping the technical direction of the company's product offerings. His previous experience includes holding esteemed positions such as Portfolio CTO at Trilogy and VP of Engineering at SoFi, where he was instrumental in driving innovative software solutions that catered to a rapidly growing user base. Additionally, Steve's tenure as CTO at Drip and CTO & CPO at InsideSales.com highlights his ability to lead product development and engineering teams toward fulfilling strategic company objectives.
Responsible for overseeing significant engineering efforts, Steve has held various leadership roles at renowned organizations such as Qualtrics, Backcountry.com, and Amazon. His contributions as VP of Engineering and Professional Services and additionally, he has worked at top financial institutions like Merrill Lynch and Citibank. He has consistently demonstrated expertise in managing software development and engineering teams, building a reputation for fostering environments that prioritize customer needs while ensuring high-quality outputs.
Education and Achievements
Steve Brain pursued his higher education at the University of Warwick, where he earned a BEng (Hons) in Computer Systems Engineering, graduating with a commendable 2:1. This strong educational foundation paved the way for his successful career in technology and software engineering.
Throughout his career, Steve has achieved numerous milestones, most notably in creating and leading engineering organizations that are scalable and sustainable, adapting to changing market demands over time. In addition to his technological expertise, he places a strong emphasis on cultivating a customer-first approach, ensuring that the software solutions delivered meet the evolving needs of users.
His passion for technology extends beyond engineering; Steve is known for his commitment to innovation and is often recognized for his capacity to transform existing organizations into high-performing teams that excel under his leadership. The culture he cultivates fosters collaboration and growth, attracting talented individuals and guiding them toward professional success.
Noteworthy Contributions
- Innovative Software Solutions: Steve's leadership has resulted in the development of several noteworthy software products that stand out in their respective markets, particularly in the financial services sector.
- Expert Team Building: Steve has a unique talent for assembling highly skilled engineering teams from the ground up, as well as transforming existing ones into productive units that consistently meet and exceed goals.
- Customer-Centric Approach: By instilling a value-driven engineering philosophy focused on customer requirements, Steve has ensured that products are not only technically robust but also aligned with user needs, driving customer satisfaction.
- Global Leadership Experience: Having worked in both the US and European markets, Steve brings a global perspective to his work, adapting strategies to fit various cultural and market contexts, which is important for software organizations operating on an international scale.
Highlights
I’m happy to share that I’m starting a new position as Chief Technology Officer at Agolo. CEO, John K. introduced me via a consulting arrangement and I was impressed and decided to join the team full time.
“Any sufficiently advanced technology is indistinguishable from magic” Arthur C Clarke.
Time to make some magic. Gen AI has a lot of promise but the gap between query engineering and real results is too large. Agolo is making Gen AI useful for enterprise clients.
In January I started a career break. It had been years in planning, and aligned with us finishing a house build and wanting time to get things straight. Since January I’ve skied a bunch in British Columbia and also in France, Italy, Switzerland and Norway. Also had plenty of time to relax, ride my bike and reflect. For those really interested, I did make a hiking trail on our property but am still figuring out how to build a mountain bike trail on a steep hillside.
However, there is more to the story than this. I also wanted to explore a startup idea I had. With the shift to 401(k) retirement plans in the 1980’s and the generations of baby boomers and increasingly Gen X retiring now, there are a significant number of Americans balancing investments and spend in their retirement. Consistent sources such as social security, final salary plans and annuities, are replaced with variable income sources based on capital market performance.
But the current tools to manage spend still use similar data models to Quicken. They focus on financial transactions, versus true units of spend. If you shop on Amazon, they want to categorize every transaction the same. In my research I found there are people who still love Quicken, but they are self diagnosed as a little obsessive compulsive. Those individuals are happy to manually categorize and split each transaction into the correct spending class. Those are not the majority of our population - most people wing it.
Building a better product is made easier today with AWS services including Quicksight (for reporting), Plaid for gathering financial transactions and LLMs to analyze and generate personalized recommendations. I was able to prototype quickly and was confident a great product could be built.
Why am I publishing this now? The short answer is I decided to abandon the endeavor. There are two reasons why, different sides of the same coin:
Price - researching the competitive landscape, consumers are willing to pay around $100/year for a solution. The appetite for a better product that costs more might justify 2x this, but it would be hard to justify 10x the price. Cost - the cost of goods sold (COGS) in this product would be impacted by the monies payable to AWS, Plaid and OpenAI. COGS impacts margin, which impacts both bootstrapping and fund raising.
It was a fascinating exercise to think through building a company from scratch. It reinforces my belief that founders need to be risk takers, and I’m probably too rational to believe the impossible. It also explains why only a small percentage of startups succeed.
From my research, I did personally start using copilot.money for my own financial tracking, as the best option I could find.
As for what’s next for me? I’ve got more tech work in my future and recently completed a tech evaluation for a startup (not Copilot or anything in this same immediate space). More to come soon.
