VP of Operations
$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 

Americas & Western Europe (UTC -8 to +2)
Flexible schedule
Fully-remote
full-time (40 hrs/week)
Long-term role

VP of Operations   $200,000 USD/year

Description

This role is for operators who can build and rebuild systems that 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

  • Executing high-complexity operational projects such as M&A integrations, enterprise system migrations, and large-scale org transitions
  • Designing and shipping automations that replace CRM and task management tools using Python and LLM APIs
  • Deploying AI-powered workflows via Cursor, Windsurf, and MCP to eliminate manual work and reduce latency
  • Leading initiatives from diagnosis to deployment, using proven playbooks and executive-level judgment
  • Completing a hands-on technical challenge to demonstrate your ability to design and implement AI-first solutions

What you will NOT be doing

  • Managing large teams or relying on layers of people to get things done
  • Sitting through endless alignment meetings or relying on consensus to move
  • 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

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.

Candidate 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

  • 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

Applying for a role? Here’s what to expect.

Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.

Pass Cognitive Aptitude Test.
STEP 1

Pass Cognitive Aptitude Test.

Pass English Proficiency Test.
STEP 2

Pass English Proficiency Test.

Prove Real-World Job & AI Skills.
STEP 3

Prove Real-World Job & AI Skills.

Ace An Interview Or Two.
STEP 4

Ace An Interview Or Two.

Accept Job Offer.
STEP 5

Accept Job Offer.

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