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
Not accepting applications on crossover.com at this time.
Description
You’re not here to babysit processes — you’re here to overhaul them. At Trilogy, we believe operational excellence is the engine behind exceptional businesses. That’s why we’re looking for operators who can see through chaos, cut the noise, and deliver streamlined, AI-powered systems that scale.
In this role, you’ll champion operational transformation — cutting through complexity, streamlining processes, and aligning high-performing teams around the metrics that matter most. Whether it’s rearchitecting support workflows, orchestrating M&A integrations, or driving millions in savings through automation and vendor consolidation, you’ll be executing the most important changes across our global software portfolio. You’ll work with proven playbooks, top-tier peers, and cutting-edge AI tools to deliver fast, lasting impact.
At Trilogy, we don’t waste time with maintenance-mode management. We believe great operations leaders are builders — of systems, efficiencies, and business value. If you’re craving the chance to make bold moves and leave behind a trail of better-run businesses, this is the job you’ve been waiting for.
What you will be doing
- Executing cross-functional operational turnarounds using the Trilogy playbook to fix what’s broken and scale what works.
- Designing and automating processes with AI tools like GPT and Cursor to eliminate manual work across departments.
- Driving high-stakes, high-complexity projects such as multi-country RIFs, system migrations, and M&A integrations.
- Diagnosing root causes of dysfunction, designing new workflows, and aligning teams around operational KPIs.
- Delivering rapid, measurable improvements in margin, retention, and organizational efficiency.
What you will NOT be doing
- Babysitting processes or managing steady-state operations — your focus is intervention and transformation.
- Sitting in endless alignment meetings — your job is to cut through misalignment and create clarity.
- Delegating to bloated teams — you’ll work lean, supported by AI and systems, not layers of management.
- Reinventing the wheel — we hand you a proven playbook so you can focus on delivering results, not drafting strategy decks.
Key responsibilities
Lead bold operational transformations that simplify systems, cut costs, and drive measurable business value across Trilogy’s portfolio companies.
Candidate requirements
- Currently based in North, Central, or South America
- 5+ years of experience in the enterprise software industry
- 5+ years in operational roles with demonstrated impact
- 3+ years in customer-facing functions (Support, Sales, Collections, etc.)
- Proven ability to leverage generative AI tools to drive efficiency and scale
You will be working for
Hundreds of software businesses run on the Trilogy Business Platform. For three decades
About Trilogy
Quick links
How it works
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.
STEP 1
Pass Cognitive Aptitude Test.
STEP 2
Pass English Proficiency Test.
STEP 3
Prove Real-World Job & AI Skills.
STEP 4
Ace An Interview Or Two.
STEP 5
Accept Job Offer.
Frequently asked questions
Why Crossover
Recruitment sucks. So we’re fixing it.
The Olympics of work
It’s super hard to qualify—extreme quality standards ensure every single team member is at the top of their game.
Premium pay for premium talent
Over 50% of new hires double or triple their previous pay. Why? Because that’s what the best person in the world is worth.
Shortlist by skills, not bias
We don’t care where you went to school, what color your hair is, or whether we can pronounce your name. Just prove you’ve got the skills.
