Senior Consultant
$200,000 USD/year ^{Pay is set based on global value, not the local market.

Most roles = hourly rate x 40 hrs x 50 weeks}($100 USD/hour)

Not accepting applications on crossover.com at this time.

Description

Are you an operator who thrives on building scalable systems from the ground up? At Trilogy, operational excellence is our secret weapon. We rapidly acquire software companies and scale them even faster, requiring leaders who design lean, automated systems rather than manage complexity with headcount.

In this role, you'll spearhead comprehensive transformations across our global portfolio. This could involve reinventing the offboarding process for over 1,200 employees post-acquisition, replacing Jira and Salesforce with AI agents, or creating automations that save thousands of manual hours. You'll move swiftly using Python, LLM APIs, and tools like Cursor, Windsurf, and MCP, guided by a set of proven playbooks that allow you to focus on results.

Trilogy manages a portfolio of over 100 products with ruthless efficiency, operating with fewer layers, faster cycles, and higher expectations than traditional enterprises. This is your opportunity to make a significant impact without the constraints of bureaucracy or large team management.

We don't do steady-state operations, outsource transformation, or hire those who need permission or a big team to deliver. We're seeking a select few deeply technical, execution-driven leaders who leverage automation and prioritize speed. If that describes you, you'll excel here.

What you will be doing

Leading complex operational projects such as M&A integrations, enterprise system migrations, and large-scale organizational transitions
Crafting and implementing automations that replace CRM and task management tools using Python and LLM APIs
Rolling out AI-driven workflows via Cursor, Windsurf, and MCP to reduce manual labor and latency
Guiding initiatives from analysis to implementation, utilizing proven playbooks and executive-level decision-making
Completing a hands-on technical challenge to showcase your ability to develop AI-centric solutions

What you will NOT be doing

Managing large teams or depending on multiple layers of personnel to accomplish tasks
Enduring endless alignment meetings or relying on consensus for progress
Delegating challenging tasks to IT or external vendors—you will design and implement solutions yourself
Maintaining steady-state operations—this role is focused on transformation and rapid execution

Key responsibilities

Develop and implement AI-driven operational systems that eradicate manual tasks, simplify complexity, and enhance scalable execution across Trilogy’s global software portfolio.

Candidate requirements

Located in North America (excluding California), South/Central America, or Western Europe (UTC -8 to UTC +2)
5+ years of operational leadership experience in enterprise software
3+ years in customer-facing roles (Support, Sales, Collections, etc.)
Proven ability to write automation scripts in Python and integrate with LLM APIs
Experience with Cursor, Windsurf, MCP, or similar tools to deliver production-grade automations
Demonstrated ability to work independently, move quickly, and achieve high-impact results without handholding

Nice to have

Experience leading large-scale organizational changes such as M&A integrations or mass offboarding
Track record of designing and launching AI-powered operational systems
Portfolio showcasing automations you have personally developed and deployed at scale

How it works

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