Description
Legacy enterprise software is riddled with complexity, technical debt, and inefficiencies that slow down innovation and drive up costs. Many products in the industry were built over a decade ago on outdated architectures, making them expensive to maintain and difficult to evolve. Companies struggle to balance modernizing these systems while continuing to deliver business value. AI presents a massive opportunity to break this cycle, but most organizations apply it superficially, failing to use it to fundamentally transform how software is developed, maintained, and operated.
Trilogy takes a radically different approach. We acquire and integrate software businesses, applying AI and automation to simplify legacy systems, reduce costs, and accelerate value delivery. Rather than treating AI as an add-on feature, we embed it at the core of product and engineering processes, automating away inefficiencies and enabling lean, high-impact teams to drive continuous improvement. This is an opportunity to lead that transformation at scale, working across a diverse portfolio of enterprise and SMB products, modernizing technical foundations, and driving strategic impact quarter after quarter.
This is not a traditional product management role focused on feature prioritization and customer messaging. Nor is it a pure engineering leadership role centered on team management. This is a technical product ownership role, where you will act as the CTO of a product, making critical technical decisions, managing trade-offs, and ensuring that AI-driven automation is replacing manual effort. You will be deeply involved in understanding legacy architectures, making long-term technical decisions, and driving execution through SaaS and centralized engineering resources.
If you’re excited by the challenge of transforming legacy software at scale, pushing the boundaries of AI in engineering, and owning the full lifecycle of technical product decisions, we encourage you to apply.
What you will be doing
- Maintaining and demonstrating deep product expertise to guide strategic decisions
- Developing technical specifications that make sound and important technical decisions and prioritize simplicity, efficiency, and long-term viability
- Implementing generative AI technologies to automate and streamline engineering processes, aligning with the strategic vision of reducing manual labor
What you will NOT be doing
- Pure people management; your business and technical acumen will play critical roles in this position
- Wasting your time in meetings, committees, and administrative tasks; we have automated management overhead so you can focus on creating business value through hands-on work
- High-level strategies without implementation guidelines; your recommendations must be based on product-level insights
Key responsibilities
- Act as the CTO of a product, owning core competencies to modernize legacy systems, optimize costs, enhance AI-driven automation, and drive business value through seamless execution and strategic decision-making.
Candidate requirements
- 7+ years of experience making the important architecture and design decisions on software projects, such as the application of architecture design patterns or significant open source technologies
- 2+ years of experience making design decisions involving the use of cloud computing services (primarily AWS)
- 4+ years of experience in positions with full technical and delivery ownership on a revenue-generating product
- Experience building product features that make advanced use of Generative AI
- Experience using Generative AI to simplify work processes