Managing Director, Trilogy (Remote) - $400,000/year USD at Crossover

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 And while you’ve worked in SaaS for many years, you don’t have a decade of outdated “leadership” learnings to unlearn.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

Key Responsibilities

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