I partnered with a trusted consultant I had worked with on previous engagements to create a new software consultancy (Gibraltar Software) focused on solving difficult application problems for customers, typically in performance-critical aspects of their platforms.

As we took on projects, we recognized the repeating needs of our customers and created Loupe (Click to read more about this project), an application monitoring product for .NET applications, that we used during engagements to gather key real-world data necessary to diagnose and solve problems.

During my 11 years with Gibraltar Software, I led the team to identify and execute a product acquisition, VistaDB, and grew our team from two people in a self-funded startup to a peak of 15 full-time and 5 contractors in three countries serving clients worldwide. I exited my daily role with Gibraltar Software in 2021 by selling our consulting organization (including myself) to our largest customer.

Strategic Consulting

• Acquisition Advisor to Private Equity firms on transactions in the Legal Services space.
• Created & Initiated a technology roadmap for a market-leading industrial eCommerce vendor, improving product response time while lowering cost and delivery timeline for new capabilities.
• Led AI & Machine Learning Proof-of-Concept projects for legal services, spawning two product offerings.

Executive Leadership Achievements

• Collaborated with consulting customers to identify a product niche within the Application Performance Monitoring (APM) market, then led the team to create and launch a Minimum Viable Product (Loupe).
• Consistently profitable with high customer retention in a highly competitive marketplace.
• Balanced revenue and effort between consulting and product development to bootstrap startup, growing the business 20% per year for its first 10 years.
• Acquired embedded database product (VistaDB) and built a team to maintain and market it.
• Sold consulting business to a key consulting customer, retaining self-supporting product business lines.
• Built product marketing discipline including directing subject matter experts to create long-tail content to drive interest, introducing marketing automation to drive customer conversion, and developing an in-person conference engagement strategy.

Technical Leadership Achievements

• Created and led a team that created a software product (Loupe) from scratch, a cloud-first multi-tenant SaaS product used by major financial and healthcare institutions, specialist engineering teams (including one Formula1 team), and more.
• Evolved Loupe from a licensed desktop sales model to a Software-as-a-Service subscription model, building a multi-region, Azure-native solution by 2014, sustaining 10TB/Day of data ingestion.
• Expanded products to include open and closed source components for multiple technology platforms, complete with documentation and test & deployment automation.
• Led multiple consulting projects with significant technical complexity and scale, typically composed of teams from multiple vendors and the customer.