Product CTO, Trilogy (Remote) - $400,000/year USD

at  Crossover

Legacy enterprise software is often bogged down by complexity and inefficiencies, leading to high costs and stunted innovation. Many of these products were built on outdated systems, making them costly to maintain and hard to upgrade. While AI offers a way out, most companies don’t fully leverage its transformative power in software development and operations.
At Trilogy, we’re changing the game. By acquiring and integrating software businesses, we use AI and automation to simplify legacy systems, cut costs, and boost value delivery. AI isn’t just a feature for us—it’s central to our product and engineering approach, eliminating inefficiencies and empowering agile teams to keep improving. This role is your chance to lead this transformation, working with a wide range of enterprise and SMB products, modernizing their technical foundations, and making a strategic impact every quarter.
This isn’t your typical product management role focused on features or customer messaging, nor is it just about engineering leadership. As a technical product owner, you’ll serve as the CTO of a product, making crucial technical choices, managing trade-offs, and ensuring AI-driven automation takes the place of manual work. You’ll delve into legacy architectures, make long-term technical decisions, and drive execution with SaaS and central engineering resources.
If transforming legacy software at scale, exploring AI’s potential in engineering, and owning the full lifecycle of technical product decisions excites you, we invite you to apply.

CANDIDATE REQUIREMENTS

• 7+ years of experience making key architecture and design decisions in software projects, including architecture design patterns or significant open source technologies.
• 2+ years of experience making design choices involving cloud computing services, mainly AWS.
• 4+ years of experience in roles with full technical and delivery ownership of a revenue-generating product.
• Experience in building product features that leverage Generative AI.
• Experience using Generative AI to simplify work processes.

THIS POSITION IS ALSO KNOWN AS:

• Principal Software Architect
• Lead Software Architect
• Cloud Architect
• Senior Software Architect

WHAT YOU WILL BE DOING

• Developing and maintaining in-depth product expertise to steer strategic decisions.
• Creating technical specifications that prioritize simplicity, efficiency, and long-term sustainability.
• Implementing generative AI technologies to automate and optimize engineering processes, aligning with the strategic aim of minimizing manual work.

WHAT YOU WILL NOT BE DOING

• Managing people; your role relies heavily on your technical and business insights.
• Spending time in meetings and administrative tasks; we’ve automated management processes so you can focus on delivering business value through hands-on involvement.
• Crafting high-level strategies without actionable guidelines; your insights should be grounded in product-specific knowledge.

KEY RESPONSIBILITIES

• Function as the CTO of a product, taking charge of core competencies to upgrade legacy systems, optimize costs, enhance AI-driven automation, and deliver business value through effective execution and strategic decision-making.