VP, Marketing

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 weve helped tens of thousands of people reach their most ambitious goals and raised $19M from world-class investors. Ambition is sacred to us and weve 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. Youll 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 peoples lives.

• 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

• 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 youve done it more than once.

• Genuine experience across both consumer and B2B marketing.

• Youve 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 dont pull playbooks off the shelf; you build them for the specific context youre 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 youre not willing to ship work that doesnt 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. Youre not above writing copy pulling a report or building a brief yourself.

• The orientation of a true startup executive. Youve 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 youre already using AI to do it.

• 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 dont 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.

Required Experience:

Exec