Director of Sales (Entertainment)

Easol • New York, NY

1d • $140,000 - $180,000

About The Position

Easol is the first AI operating system for the Experience Commerce category, designed to help experience creators run their businesses. The company aims to be a category leader in a $300bn+ market by providing a fully integrated platform that includes website, booking engine, payments, sales & marketing tools, operations, and data & insight, all powered by agentic AI. This platform enables enterprise creators to streamline, scale, and transform their businesses through a single, end-to-end system. Currently, Easol focuses on two core verticals: Music, with clients like Coachella and Live Nation, and Entertainment, including creators such as Swingers Crazy Golf and Hijingo. The company plans to deepen its product offerings in these verticals and expand into new segments. Easol is a fast-growing, well-funded business that doubled in size in 2025 and anticipates similar growth in 2026, with a key strategy being the integration of AI-centric workflows directly into the platform to transform how creators design, sell, and operate experiences. The Director of Sales for Entertainment (LBE) will lead growth in one of Easol’s core verticals. This is a senior, high-impact role reporting directly to the CEO, responsible for delivering multi-million dollar new business across mid-market and enterprise LBE operators (e.g., competitive socialising, karaoke, escape rooms, VR, and adjacent categories). LBE is a significant growth area for 2026, a rapidly expanding market currently served by a fragmented legacy stack, presenting a substantial opportunity for Easol to disrupt and become the market leader, especially as AI offers a step change in creator support. The Director of Sales will manage a significant quota, lead complex $200k+ ACV, multi-stakeholder sales cycles, and directly manage a team of 2 sales representatives. As a key Go-To-Market leader for the vertical, this role involves working cross-functionally with Marketing, Customer Success, Product, and Finance to establish a repeatable sales motion, enhance forecasting accuracy, and ensure deals are structured for long-term, sustainable revenue.

Requirements

• You’re a senior, outcomes-driven sales director who knows how to win and scale in a high-growth environment. You’re comfortable owning a meaningful number, leading complex enterprise deals end-to-end, and building a repeatable motion that improves quarter after quarter.
• Proven enterprise / mid-market seller - a strong track record delivering against a multi-million dollar quota, ideally in B2B SaaS (vertical SaaS, marketplace, or payments/take-rate models a plus).
• Experienced in complex, multi-stakeholder sales - you’ve closed $200k+ ACV deals with senior decision makers, and you’re strong on discovery, value articulation, ROI narratives, negotiation, and closing discipline.
• Commercially sharp and metric-led - you run a tight ship on pipeline generation, conversion, and forecasting, with MEDDICC-style rigour (or similar) and a high bar for CRM hygiene and deal quality.
• A high-standards people manager - you’ve line-managed and developed sales reps, you coach effectively (calls, discovery, demos, negotiation), and you know how to raise performance whilst fostering a strong culture.
• Strong cross-functional operator - you thrive in a matrix org, partnering with Marketing, CS, Product and Finance to align plans, unblock execution, and deliver outcomes.
• Customer-obsessed and market-curious - you build credibility with operators, understand how experience businesses make money and how Easol can support this, and you turn customer insight into sharper GTM and product direction.
• Bias to action - you move fast, take ownership, and bring energy, judgement, and resilience in a role that combines autonomy with high expectations. You make things happen!

Responsibilities

• Own a multi-million dollar sales quota for Entertainment (LBE) across mid-market and enterprise, consistently delivering quarterly targets through disciplined pipeline generation, conversion, and execution.
• Run complex, multi-stakeholder sales cycles for $200k+ ACV opportunities - delivering strong discovery, building clear value/ROI narratives (incl. take-rate economics), multi-threading stakeholders, and driving close plans to signature.
• Build and maintain healthy pipeline coverage, owning outbound activity and account planning in partnership with Marketing; ensure rigorous pipeline hygiene, MEDDICC-style rigour (or similar), stage discipline, and reliable forecasting.
• Line manage and develop a team of 2 sales reps, including coaching, performance management, deal support, and continuously driving productivity improvements.
• Run the LBE sales operating cadence (weekly forecast and pipeline reviews, deal strategy sessions, KPI tracking), continuously improving sales process, playbooks, and standards as the vertical scales.
• Define and execute territory / segment strategy within LBE (e.g., karaoke, VR, escape rooms, competitive socialising), sharpening ICP focus and prioritising accounts to maximise win-rate and sales efficiency.
• Partner closely with Customer Success to ensure new creators are set up for success post-sale, expectations are well set, handovers are high quality, and renewal/expansion potential is built from day one.
• Work with Finance to drive sustainable growth, ensuring deal structures protect margin and unit economics, and following clear commercial guardrails and approval processes.
• Act as a voice of the LBE market internally, collaborating with Product and the wider team to feed back customer insight, competitive intelligence, and win/loss learnings that shape roadmap priorities and strengthen our positioning.
• Be the external face of Easol in Entertainment - deepen operator relationships, shape category narratives, represent Easol at key industry moments, and turn market insight into commercial and product advantage.

Benefits

• You'll have real visibility of what's happening in the business. We have weekly company meetings, where we all get together to discuss our wins, learning opportunities, our goals and direction.
• There is an open forum for you to have your say in what we do and how we do it. We empower our team to share their ideas - no egos here!
• You'll have access to our incredible perks, such as a company-funded "deep week", where you can travel to a destination of choice and have dedicated time to focus on a project that is important to you without distraction.
• a monthly contribution towards a gym membership
• a monthly contribution towards your mobile phone contract
• an annual personal development budget
• support to choose your own equipment
• 33 days of holidays, inclusive of public holidays.
• Employees of all backgrounds and physical abilities will be supported by us in every way possible to thrive.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed
• Number of Employees: 11-50 employees