Job Description
ELITE OPERATORS WANTED: Build the Systems That Outperform the Industry
At Trilogy, operational excellence isn't a nice-to-have; it's our unfair advantage. We acquire software companies fast, and we scale them even faster. To keep up, we need executives who can design and deliver lean, automated systems—not manage complexity with headcount.
In this role, you'll own end-to-end transformations across our global portfolio. That could mean reworking how we offboard 1,200+ employees post-acquisition, replacing Jira and Salesforce with AI agents, or building automations that eliminate thousands of manual hours. You'll execute fast using Python, LLM APIs, tools like Cursor, Windsurf, and MCP—and a stack of proven playbooks that let you focus on outcomes.
Trilogy runs a 100+ product portfolio with ruthless efficiency. We operate with fewer layers, faster cycles, and higher expectations than traditional enterprise environments. This is your chance to drive impact at scale without battling bureaucracy or managing bloated teams.
We don't do steady-state ops. We don't outsource transformation. And we don't hire people who need permission or a big team to deliver. We're looking for a small number of deeply technical, execution-first leaders who use automation as leverage and speed as strategy. If that's you—you'll thrive here.
What You Will Be Doing - Execute high-stakes operational transformations including M&A integrations, enterprise system migrations, and organizational restructures with measurable business impact
- Design and deploy AI-powered automations that replace traditional CRM and task management systems using Python and advanced LLM APIs
- Build scalable workflows via Cursor, Windsurf, and MCP that systematically eliminate manual effort across the organization
- Lead mission-critical initiatives from strategic diagnosis to technical implementation using executive judgment and Trilogy's battle-tested playbooks
- Demonstrate your technical capabilities through a hands-on challenge focused on designing and implementing AI-first operational solutions
What You Won’t Be Doing - Overseeing large teams or building organizational hierarchies to accomplish objectives
- Wasting time in consensus-building meetings or navigating bureaucratic approval chains
- Outsourcing the technical implementation to IT departments or third-party vendors—you'll architect and execute solutions directly
- Maintaining status quo operations—this role exists exclusively to drive transformation and velocity
Head Of Operations Key Responsibilities Design and deploy AI-first operational systems that eliminate manual effort, compress complexity, and drive scalable execution across Trilogy's global software portfolio.
Basic Requirements - Based in North America (excluding California), South/Central America, or Western Europe (UTC -8 to UTC +2)
- 5+ years of operational leadership in enterprise software with demonstrated results
- 3+ years in customer-facing roles (Support, Sales, Collections, etc.)
- Proven ability to write production-grade automation in Python and integrate with LLM APIs
- Hands-on experience using Cursor, Windsurf, MCP, or similar tools to build and deploy automations
- Demonstrated capacity to execute independently, make high-stakes decisions, and deliver results without supervision
Nice-to-have Requirements - Track record leading complex organizational transitions such as M&A integrations or large-scale workforce restructuring
- Documented success designing and implementing AI-driven operational systems that deliver measurable business outcomes
- Portfolio of self-built automations deployed at enterprise scale with quantifiable impact metrics
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 for more details on this topic.
Crossover Job Code: LJ-5145-CA-Calgary-HeadofOperatio
Job Tags
Full time, For contractors, Long term contract, Immediate start, Remote work,