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

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 for more details on this topic.

Crossover Job Code: LJ-5145-US-Elizabet-ConsultingMana.001