CEO-in-Training, Trilogy (Remote) - $400,000/year USD

Job ID: 4649

If you think most CEOs are full of themselves (and full of other stuff)... keep reading.

Here’s a CEO track that requires — and actually rewards — zero experience being a CEO. Over the next two years, you’ll become an incredibly effective, customer-facing CEO in an environment with more than 100 software products.

Who You Are

You’ve never been a CEO before. Probably because most of the time, “CEO” is just a 3-letter code for “an exhausting hamster wheel of teambuilding and internal operations logistics.” And hopping on that hamster wheel would be a huge waste of your talent and potential.

You’re smart. You keep things clear and direct. And while you’ve worked in SaaS for 10 years or so, you don’t have a decade of outdated “leadership” learnings to unlearn. You’re ready to be the leader that smart employees like you have been waiting for. This job right here is your launchpad.

Spend two years with Trilogy, discovering the ins and outs of running a successful software business. Sure, other companies have “CEO Development” programs — but only at Trilogy will you get your hands on all departments, approach the unfamiliar with humility and curiosity, and complete a series of actually-useful assignments that turn you into an effective, respected leader.

Just two short years stand between you and a high-paying, deeply interesting CEO position.

What you will be doing
  • Living in the customer’s shoes. What’s working for them? How are we coming up short? How can we show up more effectively? Why the hell aren’t we doing that right now?
  • Seeing into the future. You’ll dig up the root causes of big problems to dream up better solutions. And blow up today’s barriers with your vision of a world without them.
  • Un-bungling SNAFUs. If you’re ever in doubt over tough decisions, don’t sweat it. Your hands-on training comes with Trilogy’s proven playbook as your guide and safety net.
What you will NOT be doing
  • Busywork that drains your creativity.
  • Day-in, day-out team management or internal operations that distract from your vision. 
  • Tinker with the business model to figure out what works. (Remember, we’re giving you the playbook.)
Candidate Requirements
  • At least 10 years of work experience in the enterprise software industry, specifically in sales, licensing, pricing, & professional-service models
  • Leadership experience in marketing, sales, business development, partnerships, or another hands-on customer-facing domain within an enterprise software company
  • Willingness to execute a proven playbook to transform a struggling business
  • Experience leading through change and managing stakeholder expectations
Apply Now


$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