Managing Director
$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)

North America, South America, or Europe
full-time (40 hrs/week)
Long-term role

Managing Director $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. In this role, 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 And while you’ve worked in SaaS for many years, you don’t have a decade of outdated “leadership” learnings to unlearn.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).

You should already be well on your way to building a strong personal brand. We believe in the importance of a personal brand, and we’ll help you develop yours. You should understand the benefits and impact of a personal brand, the long-tail nature of content, and the effort it takes.

You have experience with quickly moving products, particularly in leadership roles during the launch of epic new features. If you’ve been part of teams going from Seed through Series A/B rounds, that’s a huge plus. You’ve got proven ability to get customers excited about new product features and have used metrics like net dollar retention and win-back rates (and others) to measure the impact of new product features.

What you will be doing

  • Implementing AI-driven Productivity Improvements: Utilizing generative AI tools to streamline and automate various workflows across the company.
  • Customer Engagement and Feedback: Interacting with customers to gather insights and feedback, and using this information to enhance product offerings.
  • Develop a Personal Monopoly: Publishing podcast episodes and blog posts and building a social media following to evangelize your portfolio's AI-driven products.

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 8 years of work experience in the enterprise software industry
  • Leadership experience in marketing, sales, business development, partnerships, professional services, or another hands-on customer-facing domain
  • 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
Isuru Samarasinghe
Isuru  |  Software Engineer
Sri Lanka  

Isuru saves two hours a day by cutting his daily commute around Colombo, Sri Lanka's capital. Working remotely as a Software Engineer for Tr...

Meet Isuru
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.