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.