Earn up to

Are you a proficient written communicator who can detail the root causes of systemic issues? Are you someone who has a knack of troubleshooting operational inefficiencies?
Some of the partner organizations at Crossover are looking to onboard a skilled tech oriented professional that is skilled in dealing with customer requests and resolving technical problems, who is able to provide efficient tech support and also able to jumpstart small sets of feature requests to improve the customer experience.
In these roles, you will make bold and impactful design decisions that make customers fall in love with our support team:
The jobs can also involve translation skills, geo-spatial knowledge, and/or the ability to identify and communicate how related products support or provide solutions to the customer's request.
We have openings for multiple teams, so if you are looking for a flexible, work from home role, then this might be your opportunity to work remotely.
Across our entire organization, one of the core tenants of leadership is the ability to "stay close to the work". Our customer support leaders, therefore, spend one day per week solving actual tickets from lower-level work queues so that they are better able to identify customer pain points and process inefficiencies. Successful customer support leaders are hands-on "doers" and not "delegators".
You will spend the majority of your time deep-diving into specific areas of support that are impediments to achieving 100% customer satisfaction and making recommendations to fix systemic issues and raise quality standards. You will be responsible for setting the quality bar high through your own improvement proposals and through proposal reviews.
You will be judged by the quality of the customer service you and your team provide, and we measure it rigorously and constantly.
Support executives at Trilogy often write Important Design Decisions (IDDs) focused on optimizing our service, from L1 customer interaction playbooks to higher-level process design, and continually improving our quality bars.

This is not a normal VP role. There is no team reporting to you. No standing meetings to fill your calendar. No quarterly strategy decks. No steady-state operations to coast on.
In this role, you will run M&A diligence and integrations for enterprise software companies, own P&L targets for business units, build AI automations using the latest tools at your disposal, negotiate vendor contracts, and present directly to portfolio CEOs, CFOs, and functional leads. You will do all of this yourself, concurrently, across multiple companies.
Trilogy acquires distressed enterprise software companies and turns them around, with a target pace of one acquisition per week. The VP of Operations team is 10 people running operations across 50+ portfolio companies. The work falls into three buckets: acquisitions (end-to-end, from diligence to integration), acting as de facto COO for business units (budgets, P&L, vendors), and consulting for central functions (Support, SaaS, Engineering) to connect their work to business outcomes.
This is a high-stakes, high-visibility role where no two days look the same. You will influence decisions from key stakeholders across the organization, from portfolio CEOs to functional leads to deal-side partners. The person who thrives here does not wait for consensus; they build conviction, present the evidence, and move people to act.
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 platform purely focused on remote work like Crossover. The integration from recruitment to payday is unique.
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 platform purely focused on remote work like Crossover. The integration from recruitment to payday is unique.
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.