Director of Sales (Entertainment)

Easol is the first AI operating system for the Experience Commerce category - an intelligent digital workforce that helps experience creators (our word for client) run their business. Our ambition is bold: to become the category leader in a $300bn+ space.

We power professional experience creators with a fully integrated platform that brings together website, booking engine, payments, sales & marketing tools, operations, and data & insight - all underpinned by agentic AI. Easol enables enterprise creators to streamline, scale and transform their businesses through a single, end-to-end system.

Today, we focus on two core verticals: Music, with creators including Coachella, Live Nation and Afro Nation - and Entertainment, with creators including Swingers Crazy Golf and Hijingo. Over the next year, we’ll be deepening our product in each vertical and expanding into new segments.

We’re a fast-growing, well-funded business that has doubled in size in 2025, with a clear pathway to do the same again in 2026. A key pillar of our strategy is building AI-centric workflows directly into the platform, transforming how creators design, sell and operate their experiences.

About the role

 

We’re hiring a Director of Sales for Entertainment (LBE) to lead growth in one of Easol’s two core verticals. This is a senior, high-impact role at the centre of our Entertainment strategy, reporting directly to the CEO. You’ll be 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 key growth area for the business in 2026. Having entered the market in 2025, Easol has won flagship creators (Swingers Golf, Hijingo, Bingo Loco). It is a rapidly-growing market currently served by a fragmented legacy stack; the opportunity is huge and we are at an inflection point as AI presents a step change in how Easol can support creators. Easol is moving full steam ahead to disrupt and become the market leader.

As Director of Sales, you’ll own a significant quota and lead complex $200k+ ACV, multi-stakeholder sales cycles, while directly managing a high-quality team (2 sales reps). As a key GTM leader for the vertical, you’ll work in a matrix org alongside Marketing, Customer Success, Product and Finance to build a repeatable sales motion, improve forecasting rigour, and ensure deals are structured for long-term, sustainable revenue.

Key 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.

About You

• 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!

 

What Success Looks Like

• 3 months: fully ramped on Easol, LBE market + take-rate model; running a tight weekly cadence; coaching the team; owning key deals; building pipeline and a clear next-quarter forecast/plan.

• 6 months: closing key deals; hitting quarterly targets; developed pipeline to hit next quarter; improved win-rate/velocity and forecast accuracy; repeatable outbound + marketing motion in place; strong CS handover rhythm; clear commercial guardrails with Finance.

• 12 months: team reliably delivering annual new business targets; a high-performing team and scalable sales playbook for LBE; strong operator relationships and market presence; next-year LBE GTM plan agreed and ready to execute.

What You'll Enjoy About Easol

🧠 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.

💰 In addition to that, we offer a monthly contribution towards a gym membership and your mobile phone contract, an annual personal development budget, support to choose your own equipment and a lot more.

✈ You’ll have 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.