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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. 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 And while you’ve worked in SaaS for many years, you don’t have a decade of outdated “leadership” learnings to unlearn.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 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
- 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.
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 www.crossover.com/help-and-faqs 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 Crossover.com, 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-US-RoundRoc-VicePresidentC.018
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