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
Fully-remote
full-time (40 hrs/week)
Flexible schedule
Long-term role

Managing Director $400,000USD/year ($200 USD/hour)

Description

Ready to redefine what it means to be a CEO? This isn't your typical corner-office leadership role – it's a transformative opportunity for a customer-obsessed innovator who's ready to lead without the traditional CEO baggage.

We're seeking a visionary who can harness the power of AI, build authentic customer relationships, and drive exponential growth across our portfolio of 100+ software products. No previous CEO experience required – in fact, we prefer it that way.

As our next Managing Director, you'll combine your SaaS expertise, AI proficiency, and customer-first mindset to revolutionize how software companies operate and scale. If you've been waiting for a leadership role that actually lets you lead (instead of getting buried in operational minutiae), this is your moment.

What you will be doing

  • Spearhead AI-driven transformation initiatives across multiple software products, implementing cutting-edge solutions that drive measurable business outcomes
  • Build and nurture strategic customer relationships while crafting compelling product narratives that resonate with enterprise clients
  • Establish yourself as a thought leader in the AI-enabled software space through strategic content creation and community building

What you will NOT be doing

  • Wrestling with legacy management structures or getting bogged down in traditional corporate politics
  • Spending endless hours on operational minutiae that doesn't drive growth or innovation
  • Experimenting with unproven business models or reinventing the wheel (we have a proven playbook for success)

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
  • Advanced generative AI proficiency (i.e., use of multiple AI tools, ability to automate workflows and custom GPTs); if you've only used LLMs for research, learning, brainstorming, or content generation, that will be deemed insufficient
  • 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.
STEP 1

Pass Cognitive Aptitude Test.

Pass English Proficiency Test.
STEP 2

Pass English Proficiency Test.

Prove Real-World Job Skills.
STEP 3

Prove Real-World Job Skills.

Ace An Interview Or Two.
STEP 4

Ace An Interview Or Two.

Accept Job Offer.
STEP 5

Accept Job Offer.

Celebrate!
STEP 6

Celebrate!

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.