Chief Operating Officer
$400,000 USD/year Pay is set based on global value, not the local market. Most roles = hourly rate x 40 hrs x 50 weeks ($200 USD/hour)

Not accepting applications on at this time.


Trilogy is hunting for “fixers”. If you can wade knee-deep into failing business processes and yank out the wrenches keeping things from turning smoothly, then we’re hunting for you.

As COO of Trilogy’s 100+ software products, you’ll be in charge of transforming waste into winning. How? By simplifying overly complex operations, eliminating wasteful processes (and people), and identifying and solving operational misalignments. 

While some COO roles boil down to sitting in meetings all day, and others are one boring performance review after the next… this position will give you the power to get your hands dirty. You’ll plan and execute internal restructures that make everyone on your team say, “Wow, we should have been doing it like that from the start.”

Call us old-fashioned, but we think the role of a Chief Operating Officer should involve operating — i.e., actually taking action to create change in the short term. Maybe you do, too?

Who You Are

  • You genuinely enjoy digging into every part of a business to locate and eliminate operational inefficiencies. 
  • You’re an expert at improving internal operations to deliver more value to customers (or you would be, but you haven’t had the power to try yet).
  • You understand complex operations and quickly figure out ways to simplify them.
  • …. You may or may not have been called a “robot” by people who don’t understand getting pleasure from fixing something that’s broken.

What you will be doing

  • Turning your piercing, merciless vision on what’s working in a given division — and what’s not
  • Creating restructuring plans for specific operational functions (e.g. Customer Support, Pricing, Sales) based on the Trilogy playbook 
  • Thinking of and executing ways to solve big internal problems, work smarter, and trim the fat

What you will NOT be doing

  • High-level management and delegation. Virtually all administrative tasks and standardized work is automated for you, so you can focus on execution.
  • Overseeing steady-state operations. Once the division you’re working on is sailing smoothly, you’ll move on to the next challenge.
  • Raising equity or working on other financial projects.
  • Reinventing the startup wheel. Instead, we hand you the proven playbook for growth, and you go to town.

Key responsibilities

  • Execute proven operational and structural frameworks to turn around broken companies — we give you the playbook, you run with it (and tell us how you think it can be improved)
  • Achieve positive margins and high customer retention rates for our portfolio of software company acquisitions

Candidate requirements

  • 8+ years of experience in the enterprise software industry, building a deep understanding of software practices
  • 5+ years working in an operational role
  • 3+ years of experience in a customer-facing role (e.g., Support, Sales, Collections)
  • No C-level experience required

Meet a successful candidate

Watch Interview
Malin Raman Delin
Malin  |  Strategic Analyst
United Arab Emirates  

Juggling a high-powered career with the needs of a young family is no small feat. Malin Raman Delin found a remote job on Crossover that emp...

Meet Malin
How it works

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

We’ve curated a series of steps that take the guesswork (and cognitive bias) out of recruiting the best person.

Pass Cognitive Aptitude Test.

Pass Cognitive Aptitude Test.

Pass English Proficiency Test.

Pass English Proficiency Test.

Prove Real-World Job Skills.

Prove Real-World Job Skills.

Ace An Interview Or Two.

Ace An Interview Or Two.

Accept Job Offer.

Accept Job Offer.



Frequently asked questions

About the role

About Crossover

What you will learn

You will learn practices to transform software companies from a proven playbook. You will also learn in-depth how all functions of the company operate. Finally, you will learn the software factory model used by Trilogy that allows operating 100+ companies with maximum efficiency.

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Why Crossover

Recruitment sucks. So we’re fixing it.

The Olympics of work

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

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

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.