Head of Operations, Trilogy (Remote) - $200,000/year USD

This position is designed for operators capable of architecting and re-architecting systems built to scale.

Trilogy doesn't treat operational excellence as optional—it's the strategic advantage that defines us. Our model is to acquire software businesses rapidly and scale them even more aggressively. Sustaining that pace requires executives who design lean, automated frameworks—not those who default to adding headcount to manage complexity.

You'll take ownership of comprehensive transformations spanning our international portfolio. This might involve redesigning the offboarding process for over 1,200 employees following an acquisition, substituting Jira and Salesforce with AI-driven agents, or constructing automations that remove thousands of hours of manual labor. Execution will be rapid, leveraging Python, LLM APIs, and tools including Cursor, Windsurf, and MCP—supported by a library of battle-tested playbooks that keep you focused on measurable results.

Trilogy operates a portfolio exceeding 100 products with disciplined efficiency. We function with reduced hierarchy, accelerated iteration, and elevated standards compared to conventional enterprise settings. This is an opportunity to generate large-scale impact without navigating bureaucracy or overseeing inflated teams.

Steady-state operations aren't our focus. Transformation is not outsourced. We don't bring on people who require consensus or extensive teams to produce results. Our search is for a select group of deeply technical, execution-oriented leaders who treat automation as leverage and velocity as core strategy. If that describes you—this environment will suit you well.

What You Will Be Doing

* Leading high-complexity operational initiatives including M&A integrations, enterprise platform migrations, and organization-wide transitions

* Architecting and delivering automations that replace CRM and task management platforms using Python and LLM APIs

* Implementing AI-enabled workflows through Cursor, Windsurf, and MCP to remove manual processes and decrease response time

* Driving projects from assessment through deployment, applying established playbooks and executive decision-making

* Completing a practical technical assessment to validate your capability to design and deliver AI-first solutions

What You Won’t Be Doing

* Building or managing large teams or depending on organizational layers to execute work

* Participating in prolonged alignment sessions or waiting for consensus before taking action

* Handing off the complex work to IT departments or third-party vendors—you'll design and implement the solution directly

* Running steady-state operations—this position centers on transformation and speed

Head Of Operations Key Responsibilities

Architect and implement AI-first operational frameworks that remove manual workload, reduce complexity, and enable scalable execution throughout Trilogy's worldwide software portfolio.

Basic Requirements

* 5+ years of operational leadership in business operations

* Experience presenting to C-suite executives

* Experience building automation in Python and integrating with LLM APIs

* Experience deploying production-grade automations using Cursor, Windsurf, MCP, or similar tools

* Remote work capability with at least 6 hours of overlap with the CST time zone

About Trilogy

Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things: Relentlessly seeking top talent, Innovating new technology, and incubating new businesses. Our technological innovation is spearheaded by a passion for simple customer-facing designs. Our incubation of new businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today's modern cloud-based stack. Trilogy is a place where you can be surrounded with great people, be proud of doing great work, and grow your career by leaps and bounds.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with us

This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5145-DE-Berlin-HeadofOperatio.002