Consulting Manager, Trilogy (Remote) - $200,000 / year USD

Trilogy; Montreal; Remote; CAD 276,000; Full time

Job summary

A global software company is seeking a Consulting Manager to lead high-complexity operational projects and drive automation across its global portfolio. The role requires strong operational leadership and experience in customer-facing roles, leveraging Python and LLM APIs. This is a full-time position at $200,000 per year, offering the chance to create impactful change without the constraints of bureaucracy.

Qualifications

• 5+ years of operational leadership in enterprise software
• 3+ years in customer-facing roles
• Proven ability to move fast and deliver high-stakes results

Responsibilities

• Execute high-complexity operational projects including M&A integrations
• Design automations to replace CRM and task management tools
• Lead initiatives from diagnosis to deployment

Skills

Operational leadership in enterprise software

Automation with Python

Experience with LLM APIs

Using tools like Cursor, Windsurf, MCP

Customer-facing roles experience

Tools

Python

Cursor

Windsurf

MCP

Job description

Consulting Manager, Trilogy (Remote) - $200,000 / year USD

Join to apply for the Consulting Manager, Trilogy (Remote) - $200,000 / year USD role at Trilogy

Consulting Manager, Trilogy (Remote) - $200,000 / year USD

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Join to apply for the Consulting Manager, Trilogy (Remote) - $200,000 / year USD role at Trilogy

This range is provided by Trilogy. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.

Base pay range

100.00 / hr - $100.00 / hr

MASTER SYSTEMS BUILDER : Transform how global software companies operate at scale.

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-complexity operational projects including M&A integrations, enterprise system migrations, and large-scale organizational transitions
• Design and ship automations that replace traditional CRM and task management tools using Python and LLM APIs
• Deploy AI-powered workflows via Cursor, Windsurf, and MCP to eliminate manual work and reduce operational latency
• Lead initiatives from diagnosis to deployment, applying proven playbooks with executive-level judgment
• Complete hands-on technical challenges demonstrating your ability to architect and implement AI-first solutions

What You Won’t Be Doing

Managing large teams or relying on layers of people to get things done

Sitting through endless alignment meetings or waiting for consensus to take action

Delegating the hard work to IT or external vendors—you'll architect and execute the solution yourself

Maintaining steady-state operations—this role is built around transformation and velocity

Consulting Manager 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

3+ years in customer-facing roles (Support, Sales, Collections, etc.)

Demonstrated ability to write automation in Python and integrate with LLM APIs

Experience using Cursor, Windsurf, MCP, or similar tools to ship production-grade automations

Proven ability to move fast, think independently, and deliver high-stakes results without handholding

Nice-to-have Requirements

Experience leading large-scale organizational transitions such as M&A integrations or mass offboarding

History of designing and deploying AI-driven operational systems

Portfolio of automations you've personally built and shipped at scale

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-CA-Montreal-ConsultingMana.002

Seniority level

Seniority level

Director

Employment type

Employment type

Full-time

Job function

Job function

Consulting

Industries

Software Development, IT Services and IT Consulting, and Business Consulting and Services

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