Managing Director, Trilogy (Remote) – $400,000/year USD


Crossover is the world’s #1 source of full-time remote jobs. Our clients offer top-tier pay for top-tier talent. We’re recruiting this role for our client, Trilogy. Have you got what it takes?

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 team building 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 And while you’ve worked in SaaS for 10 years or so, you don’t have a decade of outdated “leadership” learnings to unlearn.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.

You’re a generative AI power user. You’ve used ChatGPT, Claude, Bard, or a similar tool to automate previously manual workflows (note: this role does not require a software development background).

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

  • Using generative AI to realize major productivity gains throughout the company, with the ultimate goal of automating entire departments.
  • 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 Won’t 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.)

Basic Requirements

Managing Director key responsibilities

  • 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
  • Experience using generative AI tools to achieve quantifiable productivity improvements
  • Currently based in North America, South America, or Europe

About Trilogy

Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things: Relentlessly seeking top talent, Innovating new technology, and incubating new businesses. Our technological innovation is spearheaded by a passion for simple customer-facing designs. Our incubation of new businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today’s modern cloud-based stack. Trilogy is a place where you can be surrounded with great people, be proud of doing great work, and grow your career by leaps and bounds.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with Crossover

This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover. The compensation level for this role is $200 USD/hour, which equates to $400,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult for more details on this topic.

What to expect next:

  • You will receive an email with a link to start your self-paced, online job application.
  • Our hiring platform will guide you through a series of online “screening” assessments to check for basic job fit, job-related skills, and finally a few real-world job-specific assignments.

Important! If you do not receive an email from us:

  • First, emails may take up to 15 minutes to send, refresh and check again.
  • Second, check your spam and junk folders for an email from, mark as “Not Spam” since you will receive other emails as well.
  • Third, we will send to whatever email account you indicated on the Apply form – by default, that is the email address you use as your LinkedIn username and it might be different than the one you have already checked.
  • If all else fails, just reset your password by visiting if you already applied using LinkedIn EasyApply.

Crossover Job Code: LJ-4649-CA-Mississa-ManagingDirect.007