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Legacy enterprise software is suffocating under its own complexity. These systems—many built decades ago on outdated foundations—have accumulated crippling technical debt that hampers innovation and drives costs skyward. While organizations recognize the need for modernization, they often settle for band-aid solutions rather than meaningful transformation. The AI revolution offers a pathway to break free from this cycle, yet most companies merely sprinkle AI capabilities onto existing processes—a superficial approach that fails to capture the transformative potential of this technology.
At Trilogy, we're revolutionizing how software businesses evolve. As part of a strategic M&A group, we don't just acquire software companies—we reimagine them. By weaving AI and automation into the very fabric of these organizations, we're creating leaner, more agile operations that deliver exceptional value. Our philosophy rejects the conventional "AI as an add-on" approach, instead rebuilding systems from the ground up with intelligence and efficiency at their core. The result? Streamlined architectures, dramatically reduced operational overhead, and accelerated value delivery across our diverse portfolio of enterprise and SMB solutions.
This Principal Architect role transcends traditional boundaries. You won't be confined to product roadmapping or team management—you'll assume comprehensive ownership of acquired products, serving as their technical guardian and visionary. Your mandate includes ensuring robust system health, optimizing performance metrics, swiftly addressing critical issues, and orchestrating both immediate stability and long-term architectural evolution. You'll spearhead the AI automation revolution, systematically replacing manual processes with intelligent systems while making pivotal technical decisions that reshape legacy architectures. Working in concert with business units and product teams, you'll translate strategic objectives into concrete technical outcomes that directly enhance product performance and profitability.
Our high-performance, fully remote team operates with exceptional autonomy and velocity, measuring success through tangible results rather than process adherence. This position demands a technical leader who thrives in high-stakes environments and embraces end-to-end ownership—not someone seeking a narrowly defined technical specialty. If you're energized by the prospect of modernizing complex systems through AI-driven transformation and making consequential decisions that redefine entire products, this role represents a rare opportunity to shape the future of software at scale.
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.
Join the world's largest community of AI-first remote workers.