Chief Operating Officer, Trilogy (Remote) - $400,000/year USD

Job ID: 4160

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


$400k/year ($200/hour)



full-time Job

40 hours/week any timezone

Employment Type

Long-term role

More about this role
More about this role