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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 Many products in the industry were built over a decade ago on outdated architectures, making them expensive to maintain and difficult to evolve.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.
Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.
It’s super hard to qualify—extreme quality standards ensure every single team member is at the top of their game.
Over 50% of new hires double or triple their previous pay. Why? Because that’s what the best person in the world is worth.
We don’t care where you went to school, what color your hair is, or whether we can pronounce your name. Just prove you’ve got the skills.