Director of Sales (Entertainment)

Easol•New York, NY

15h•Remote

About The Position

Easol is seeking a Director of Sales for Entertainment (LBE) to 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. The LBE market is a key growth area for Easol in 2026, with significant opportunity due to a fragmented legacy stack and the disruptive potential of AI. As Director of Sales, you will own a significant quota, lead complex sales cycles for $200k+ ACV opportunities, and manage a team of 2 sales representatives. You will collaborate with Marketing, Customer Success, Product, and Finance to build a repeatable sales motion, improve forecasting, and ensure sustainable revenue.

Requirements

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, 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, 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.