Leland is building the home for ambition in the age of AI. We connect people with the experts, programs, and communities they need to land the job, get into the school, or upskill for a world being rewritten by AI. We help businesses become AI-native through training, hiring, and infrastructure. Since our founding in 2021, we've helped tens of thousands of people reach their most ambitious goals and raised $19M from world-class investors. Ambition is sacred to us, and we've built a product that takes that seriously.

We are looking for our first VP, Marketing to build the engine that helps us reach more people and businesses. This is a full-ownership role: consumer and B2B, brand to demand gen, strategy to execution. You'll report to our CEO and Founder, John Koelliker, build and lead the marketing team, and own the growth number on both sides of the business. We move fast, hold a high bar, and do work that changes people's lives.

What You'll Own

• Demand generation across consumer and B2B, with clear ownership of the growth number on both sides

• Building and leading the marketing team: hiring, developing talent, and setting the performance bar

• Brand, content, and community strategy, with a strong bias toward channels that actually move the needle

• Own go-to-market for new products and categories in partnership with product and sales, from positioning and messaging through launch and into pipeline, making sure what we build finds the right customers fast

• Identify and test new growth channels systematically, from SEO to events to partnerships to community-driven distribution, and scale what proves out

• The full marketing tech stack, including attribution, analytics, and automation

• Marketing performance reporting to the CEO and leadership team

What We're Looking For

• A track record of building scalable marketing engines. You know what it feels like to take a channel or a motion from traction to scale, and you've done it more than once.

• Genuine experience across both consumer and B2B marketing.

• You've hired and led talent-dense marketing teams. You invest in the people you lead, and your former reports tend to go on to do great things.

• A first-principles thinker. You don't pull playbooks off the shelf; you build them for the specific context you're in.

• Strong commercial instincts. You feel personal ownership over the revenue number and know how your work connects to it.

• High taste and a strong point of view on what good looks like. You notice when something is off, you care why, and you're not willing to ship work that doesn't clear the bar.

• An experimental mindset backed by analytical rigor. You run structured tests, move quickly on what the data says, and know the difference between a trend and noise.

• Bias for action and willingness to be in the weeds. You're not above writing copy, pulling a report, or building a brief yourself.

• The orientation of a true startup executive. You've built in ambiguous, resource-constrained environments and you understand the job is to figure it out, not wait for more clarity or more headcount.

• High agency and AI fluency. You know how to get more done with less, and you're already using AI to do it.

Why Leland?

• The chance to join a world-class team helping people achieve their career and educational dreams

• Work in a collaborative, high-energy environment where your contributions have a direct impact

• Operate in a fast-paced, AI-native environment

• We don't hire people who merely want to work for a great company; we hire people who want to make a great company

Leland is an equal opportunity employer. We encourage candidates of all backgrounds and demographics to apply.