Enterprise Account Executive
$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)

Any country
full-time (40 hrs/week)
Long-term role

Enterprise Account Executive $400,000USD/year ($200 USD/hour)


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 And while you’ve worked in SaaS for 10 years or so, you don’t have a decade of outdated “leadership” learnings to unlearn.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 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
  • Experience using generative AI tools to achieve quantifiable productivity improvements
  • Currently based in North America, South America, or Europe

Meet a successful candidate

Watch Interview
Steve Brain
Steve  |  EVP of Technical Product Management
United States  

What happens in tech when you follow the innovation? This outside-of-the-box thinker took unconventional risks all the way to the top. As Tr...

Meet Steve
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 a proven playbook that has successfully transformed struggling software companies for over a decade. You will learn to identify inefficiencies in processes and systems and then quickly deploy solutions.

Work examples

You’ll dive deep into a variety of business domains in this role. Some of the projects you might work on include:

  • Building SEO for a product to double lead volume
  • Taking a lagging product and creating a vision that differentiates it from the competition and revitalizes its market image
  • Coaching an ineffective inbound sales team to double their MQL to Close ratio
  • Rebuilding a pre-sales organization into an enterprise SaaS team that wins large RFP-based deals
  • Creating a customer success team from scratch in a recent acquisition and doubling NPS as a result
  • Taking a company that was acquired through bankruptcy and meeting with customers to explain the new vision, model, and firm financial footing.
  • Analyzing the installed base of an acquisition to find pricing anomalies that allow you to double the yield and implementing changes based on your insights.
  • Rebuilding teams with a remote-first, global, asynchronous communication model.

Meet some people who've landed similar jobs

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.