Earn up to

Do you enjoy digging into the details of every function to locate and eliminate operational inefficiencies? Are you an expert at improving internal operations to deliver more value to customers?
Forget about high-level management or sitting in meetings all day debating how to solve one problem. This role will have you transforming business processes through hands-on work, diving deep into each function to find the root cause of operational misalignments, and building restructuring plans to align with our proven playbook for fixing software companies.
This job will keep you focused on the faster-than-fastwork-paced startup. You'll handle the complex web of problem-solving, project-reporting and team-directing with grace and ease, turning travel-intensive environments into the environment you need most.
If you want to be part of a world-class software factory in a revolutionary remote environment, we invite you to join our team!
Creating operational plans aligned to our playbooks specific to each function (e.g., Customer Support, Pricing, Sales)
Usually, similar roles are heavily taxed with administrative activities and sit far from day-to-day operations, leaving executives restricted to high-level management and delegation of all the work to direct reports. These roles allows you to investigate functions and build restructuring plans first-hand, creating fixes with unparalleled speed and impact while providing unique learning opportunities.
The most successful people in these roles are:
The roles have broad scope and fast pace - you will work with problems from different functions across multiple companies, and iterate on your plans in weeks instead of years. If you like to oversee steady-state operations or prefer year-long planning cycles, this is not your role.
You will learn practices to transform software companies from a proven playbook. You will also learn in-depth how all functions of the company operate. Finally, you will learn the software factory model that allows operating 100+ companies with maximum efficiency.

Design and deliver portfolio-wide transformation programs that measurably improve retention, cloud efficiency, and acquisition integration — with executive visibility and direct & impact.
If you’re the kind of operator who wants to own multi-million-dollar outcomes — not advise, not report, but deliver — this role is built for you. You’ll take charge of the highest-stakes operational challenges across a global software portfolio and turn ambiguity into measurable financial impact. You’ll architect the programs, drive the execution, and see your work show up directly in margin, retention, and acquisition integration performance.
Trilogy runs a large, diverse portfolio of enterprise software companies, each with complex operational patterns and material financial upside waiting to be unlocked. You’ll lead the transformations that make that upside real. Whether you’re scaling a $2M/quarter renewal uplift initiative, cutting cloud costs without touching performance, or onboarding a newly acquired business into the Trilogy model within 30 days, your work will be visible at the top of the organization. You will directly influence profitability across dozens of business units.
This role is designed for a candidate who thrives in high-exposure, high-autonomy environments. You’ll use advanced AI tools like Claude Code to accelerate analysis, structure insights, and drive impact faster than traditional operating teams can move. You won’t be bound by hierarchy or bureaucracy; you’ll have the space — and the expectation — to create clarity, build alignment, and execute decisively. If you’re energized by turning complex operational puzzles into consistent, repeatable wins, you will excel here. Apply if you’re ready to lead transformative work that changes how an entire software portfolio performs.
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.






We've developed an agentic team of AI engineers who create code, review it, and even manage repositories.
The flexibility to manage my time plus weekly scheduled payments gives me both freedom and stability.
Our AI copilots write reports for clients explaining what their child learned each week—it's amazing technology.
Getting full autonomy over my work with thorough team support creates the perfect balance.
My favorite part is the relentless focus on exponential learning—we spend an hour daily updating our AI-powered second brain.
There isn't another work platform that is purely focussed on remote work like Crossover. The integration of everything from recruitment to payday is unique. I can do my work wherever and whenever I like, and I don't even have to fill in any timesheets. Having been through the stringent job application p...
My proudest moment was achieving a seemingly impossible goal: 75% AI resolution rates across support.
My salary has quadrupled since day one—no switching companies required.
When a difficult challenge impacted my health, this job provided excellent support throughout.
AI is embedded in almost everything we do—it's not just a tool, it's how we work.
We've developed an agentic team of AI engineers who create code, review it, and even manage repositories.
The flexibility to manage my time plus weekly scheduled payments gives me both freedom and stability.
Our AI copilots write reports for clients explaining what their child learned each week—it's amazing technology.
Getting full autonomy over my work with thorough team support creates the perfect balance.
My favorite part is the relentless focus on exponential learning—we spend an hour daily updating our AI-powered second brain.
There isn't another work platform that is purely focussed on remote work like Crossover. The integration of everything from recruitment to payday is unique. I can do my work wherever and whenever I like, and I don't even have to fill in any timesheets. Having been through the stringent job application p...
My proudest moment was achieving a seemingly impossible goal: 75% AI resolution rates across support.
My salary has quadrupled since day one—no switching companies required.
When a difficult challenge impacted my health, this job provided excellent support throughout.
AI is embedded in almost everything we do—it's not just a tool, it's how we work.
Join the world's largest community of AI-first remote workers.