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VP of Operations
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SVP of Operations @ Trilogy
Worldwide
Semi-flexible schedule
Fully-remote
full-time (40 hrs/week)
Long-term role
Key responsibilities
Design and deliver portfolio-wide transformation programs that measurably improve retention, cloud efficiency, and acquisition integration — with executive visibility and direct & impact.
Description
If you’re the kind of operator who wants to own multi-million-dollar outcomes — not advise, not report, but deliver — this role is built for you. You’ll take charge of the highest-stakes operational challenges across a global software portfolio and turn ambiguity into measurable financial impact. You’ll architect the programs, drive the execution, and see your work show up directly in margin, retention, and acquisition integration performance.
Trilogy runs a large, diverse portfolio of enterprise software companies, each with complex operational patterns and material financial upside waiting to be unlocked. You’ll lead the transformations that make that upside real. Whether you’re scaling a $2M/quarter renewal uplift initiative, cutting cloud costs without touching performance, or onboarding a newly acquired business into the Trilogy model within 30 days, your work will be visible at the top of the organization. You will directly influence profitability across dozens of business units.
This role is designed for a candidate who thrives in high-exposure, high-autonomy environments. You’ll use advanced AI tools like Claude Code to accelerate analysis, structure insights, and drive impact faster than traditional operating teams can move. You won’t be bound by hierarchy or bureaucracy; you’ll have the space — and the expectation — to create clarity, build alignment, and execute decisively. If you’re energized by turning complex operational puzzles into consistent, repeatable wins, you will excel here. Apply if you’re ready to lead transformative work that changes how an entire software portfolio performs.
Candidate requirements
- 5+ years leading multi-functional operational or transformation initiatives with ≥$3M annual financial impact.
- Proven ability to analyze large, complex datasets and translate insights into validated outcomes of ≥ $500K.
- Experience optimizing cloud infrastructure costs (AWS or equivalent) with clear examples of savings and performance preservation.
- Strong financial literacy: P&L interpretation, budgeting, ROI modeling, and prioritization using financial logic.
- Familiarity with AI tools such as Claude Code, Codex, or Gemini CLI to automate analysis and improve execution.
- Remote work capability with at least 6 hours of CST overlap.
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
Chat-style screening interview.
STEP 2
Cognitive aptitude test.
STEP 3
Prove real-world job skills.
STEP 4
Interview with the hiring manager.
STEP 6
Accept job offer.
STEP 5
Pass proctored test.
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.
Meet some of the 5,000+ rockstars who have found a rewarding AI-first remote career on Crossover.
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