Management Consultant, Trilogy (Remote) - $200,000/year USD
Trilogy
Date: 4 days ago
City: Mississauga, ON
Contract type: Full time
Remote

Join the elite ranks of operators at Trilogy, where building and rebuilding scalable systems is your playground. If operational excellence is your game, we've got the ultimate arena for you.
What You Will Be Doing
Spearhead the design and deployment of AI-first operational systems that eradicate manual effort, simplify complexity, and ensure scalable execution across Trilogy's expansive software portfolio.
Basic Requirements
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-CA-Mississa-ManagementCons.020
What You Will Be Doing
- Lead high-impact operational projects, including M&A integrations and enterprise system migrations, with precision and speed.
- Innovate by designing and implementing automations to replace traditional CRM and task management tools using Python and LLM APIs.
- Utilize AI-powered workflows via cutting-edge tools like Cursor, Windsurf, and MCP to streamline processes and eliminate manual tasks.
- Drive initiatives from concept to execution, leveraging proven playbooks and your executive acumen.
- Showcase your technical skills by completing hands-on challenges focused on AI-first solutions.
- Managing sizable teams or relying on hierarchical structures to achieve results.
- Enduring endless meetings for alignment or seeking consensus before acting.
- Outsourcing complex tasks to IT or external vendors—you're the architect and executor.
- Maintaining status quo operations—your focus is on transformation and rapid execution.
Spearhead the design and deployment of AI-first operational systems that eradicate manual effort, simplify complexity, and ensure scalable execution across Trilogy's expansive software portfolio.
Basic Requirements
- Located in North America (excluding California), South/Central America, or Western Europe (UTC -8 to UTC +2).
- Minimum of 5 years in operational leadership within enterprise software.
- At least 3 years in customer-facing roles such as Support, Sales, or Collections.
- Proficiency in writing automation scripts in Python and integrating with LLM APIs.
- Experience with tools like Cursor, Windsurf, MCP, or similar for deploying production-grade automations.
- Track record of independent thinking, rapid execution, and delivering high-stakes results without supervision.
- Background in leading significant organizational transitions, including M&A integrations and mass offboarding.
- Experience in designing and deploying AI-driven operational systems.
- Showcase of automations you've personally developed and deployed at scale.
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-CA-Mississa-ManagementCons.020
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