VP Revenue

This is a fully remote position, open to applicants in New York.

📋 Description

• Take charge of all revenue aspects. The entire revenue organization reports directly to you — one cohesive team, one leader. New business development, client success, and account management form the frontline, supported by enablement and operations — the training and tools that empower them to succeed. The ultimate objective is to enhance ARR — by securing new business and ensuring our customers thrive. Your performance will be evaluated based on two key metrics: new ARR and gross retention.

• Develop a straightforward, repeatable sales process. Create a clear pathway from the initial call to closing the deal and renewal — outlining stages, standards, and playbooks that the entire team follows uniformly. Ensure it's so transparent that representatives understand what success looks like and can focus their efforts on selling rather than speculating. When executed effectively, this will result in reliable forecasts, expedited deals, and improved conversion rates at every stage.

• Cultivate the talent of our sales team. Our representatives are early in their careers and eager to learn, so developing their skills is not an ancillary task — it is central to the role. You will design the system that facilitates this: ramp-up plans, enablement strategies, and a consistent coaching schedule. You will be actively involved — participating in deals and performance reviews, providing coaching on fundamental skills in real-time, rather than waiting until the end of the quarter. The outcome is representatives who sell with genuine confidence and conviction: they understand how to succeed, and they believe they can.

• Advance our market position. Our next phase of growth focuses on securing larger deals. You recognize where the significant opportunities lie in higher education, and you will direct the team accordingly — increasing the ACV we target, concentrating on high-value accounts, and expanding those with substantial potential. This requires keen market insight, numerical acumen, and the discipline to decline less valuable opportunities.

• Manage revenue operations with an AI-driven approach. Most revenue organizations still function as they did decades ago — we will not. We specialize in AI, and the entire company is becoming significantly more efficient, accurate, and effective by leveraging AI to automate manual tasks. This demands more than merely seeking the next AI tool — it requires creativity: envisioning how technology can transform our work, and then implementing those visions.

⛳️ Requirements

• You have led a complete revenue organization — encompassing both new business and retention — and have personally met revenue targets, not just overseen others who have.

• When targets are missed, you immediately analyze the funnel metrics — pipeline, conversion rates, time spent in each stage — rather than focusing on the narrative behind the numbers.

• You have established a successful sales system — whether you built it from the ground up or revamped a dysfunctional one within an existing organization.

• You are a genuine coach. You have transformed early-career representatives into successful closers — actively engaging with them, not just observing from a dashboard.

• You possess a strong understanding of unit economics and can quickly analyze market trends. You have guided a team towards larger, more lucrative deals while maintaining the discipline to walk away from less advantageous options.

• You are already utilizing AI to innovate your workflows and do not seek permission to push its boundaries further.

• Experience in higher education or EdTech is a significant advantage, though not mandatory. The market has its complexities — if you lack direct experience, demonstrate how you will bridge that gap swiftly.

🏝️ Benefits

• Comprehensive medical, dental, and vision insurance

• 401K plan with company matching: 100% of the first 3% and 50% of the next 2%

• Flexible paid time off

• Competitive leave policies

• 13 paid holidays, including a week off between Christmas and New Year’s