Crossover · 2 days ago
Head of Operations, Trilogy (Remote) - $200,000/year USD
United States
Full-time
Remote
Lead/Staff, Director/Executive
$200K/yr - $200K/yr
5+ years expCrossover is a leading company known for acquiring and scaling software businesses rapidly. They are seeking a Head of Operations to lead high-stakes operational initiatives, architect AI-first operational infrastructures, and drive transformations across their global portfolio of software products.
Information Technology & Services
Responsibilities
Leading high-stakes operational initiatives including M&A integrations, enterprise platform migrations, and organization-wide transitions
Building and deploying automations that replace traditional CRM and task management systems using Python and LLM APIs
Implementing AI-enabled workflows through Cursor, Windsurf, and MCP to remove manual processes and shorten cycle times
Driving projects from initial assessment through full deployment, applying proven playbooks and executive decision-making
Completing a practical technical assessment to validate your capability in designing and delivering AI-first operational solutions
Qualification
Required
Located in North America (excluding California), South/Central America, or Western Europe (UTC -8 to UTC +2)
5+ years leading operations in enterprise software environments
3+ years in customer-facing functions (Support, Sales, Collections, etc.)
Proven capability to develop automation using Python and work with LLM APIs
Hands-on experience deploying production-grade automations with Cursor, Windsurf, MCP, or equivalent tools
Track record of moving quickly, thinking independently, and delivering critical outcomes without supervision
Preferred
Background in executing large-scale organizational changes such as M&A integrations or mass offboarding initiatives
Track record of building and launching AI-powered operational systems
A collection of automations you have personally developed and deployed in production environments
Company
Crossover
Crossover is a global recruitment company, founded in 2014.
5001-10000 employees
Funding
Current Stage
Late StageLeadership Team
Brad Weinert
COO
Recent News
2025-04-12
Geeky Gadgets
2025-01-24
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