VP, Sales, Live Entertainment

confidential; United States; Hybrid; USD 239,000 - 273,000; Full time

Benefits offered by this job

Hybrid work model

Comprehensive benefits

Job summary

Cast & Crew is seeking a VP of Sales to develop and execute a robust sales strategy across entertainment payroll and live entertainment markets. You will identify partnerships, drive revenue, and lead cross‑functional teams to meet ambitious targets.

Travel 25% is required, and a hybrid work model is offered. The ideal candidate has 12–15 years in progressive sales, with 7+ years leading teams, plus a proven ability to exceed revenue goals and build durable client relationships in the

Qualifications

• 12–15 years of progressive sales and business development experience in entertainment payroll/live entertainment spaces.
• At least 7 years of experience leading, developing, and scaling high-performing sales teams and setting strategy.
• Proven track record of exceeding revenue targets and driving long-term customer growth.
• Strong understanding of the live entertainment marketplace, players, and buying centers.
• Executive-level presence with negotiation, presentation, storytelling, and C-suite influence.
• Strategic, commercially minded with ability to translate market intelligence into go-to-market priorities.
• Exceptional ability to build and manage relationships across multiple organizational levels.
• Self-directed, ambitious, and accountable in a fast-paced, relationship-driven industry.
• Willingness to travel periodically for industry events and client meetings.
• Established network in entertainment industry preferred.
• Hands-on experience using AI tools with measurable business impact.

Responsibilities

• Define and execute the sales strategy from prospecting to closure.
• Oversee sales operations and end-to-end process including lead generation, proposals, negotiations, closing, and post-sales support.
• Develop and maintain key client relationships and expand the customer base.
• Implement sales strategies to meet or exceed revenue targets and maximize ROI.
• Lead, coach, and scale the sales team to achieve targets.
• Collaborate with internal teams to align strategies and identify growth opportunities.

Skills

Sales leadership

Entertainment payroll

Strategic planning

Client relationships

Negotiation

Executive presence

AI tools

Tools

AI tools

Job description

About Us

At Cast & Crew, we’ve empowered creativity and supported the global entertainment industry for decades. Together with our family of brands - Backstage, CAPS, Checks & Balances, Final Draft, Media Services, Sargent-Disc, and The TEAM Companies – we operate as a combined entertainment technology and services provider offering industry standard screenwriting accounting software, digital payroll products, data & reporting, and a host of creative tools. The industry continues to move faster than ever, and the need for our expertise, our technology, and our people has never been greater. We are a production’s best ally every step of the way.#OneCastOneCrew

Position Overview

The VP, Sales develops and executes a robust sales strategy to cultivate new business and drive revenue and growth across existing and new market segments.

This position is responsible for identifying, securing, and cultivating partnerships, new business and will work cross-functionally to develop and execute strategic sales plans that drive engagement, awareness, and client satisfaction. Additionally, the VP of Sales provides oversight to the day-to-day operations of the sales team align on strategic objectives and ensure individual, team, and company goals are met.

This role requires demonstrated experience driving high pipelines growth within the entertainment industry.

Core Responsibilities

• Define and execute the sales strategy, and manage the sales cycle, from prospecting to closure.
• Oversee sales operations and manage the end-to-end sales process including lead generation, proposal development, negotiation, closing, and post-sales support.
• Develop and maintain key client relationships and implement strategies for expanding the company's customer base.
• Implement comprehensive sales strategies to meet or exceed company revenue targets, maximize ROI and achieve individual and team revenue goals.
• Serve as a subject matter expert within the assigned market to provide consultative support, recommendations, and foster a long-term partnership.
• Oversee campaign execution process to ensure client success and drive future growth opportunities.
• Lead, inspire, and motivate the sales organization to achieve monthly, quarterly, and annual revenue growth targets by establishing sales quotas and holding the team accountable to efficiently hitting and exceeding targets.
• Lead, motivate, and scale the sales team through coaching, mentoring and experience.
• Develop and build the sales team to achieve their individual and collective targets
• Engage with various internal teams to align strategies, and identify, evolve, and create sales opportunities.
• Understand the competitive landscape and market trends to influence our positioning and identify growth opportunities
• Participate in industry events and conferences.

Required Qualifications

• 12–15 years of progressive sales and business development experience, with deep expertise in entertainment payroll and the live entertainment ecosystem.
• At least 7 years of experience leading, developing, and scaling high-performing sales teams, including setting strategy, managing performance, and building leadership talent.
• Demonstrated success as a senior sales leader selling complex, consultative services solutions to live entertainment spaces.
• Proven track record of exceeding revenue targets, building a sustainable pipeline, expanding strategic accounts, and driving long-term customer growth.
• Strong understanding of the live entertainment marketplace, including its key players, business models, buying centers, competitive dynamics, and emerging trends.
• Executive-level presence with outstanding negotiation, presentation, storytelling, and communication skills; able to influence C-suite stakeholders and align cross-functional teams.
• Strategic and commercially minded, with the ability to translate market intelligence into clear go-to-market priorities, differentiated value propositions, and measurable sales outcomes.
• Exceptional ability to build and manage relationships across multiple levels of an organization, from operational users and production teams to finance leaders and executive decision-makers.
• Self-directed, ambitious, and accountable, with the judgment and resilience to operate effectively in a fast-paced, relationship-driven industry.
• Willingness and ability to travel periodically for industry conferences, client meetings, events, and other business-development activities.
• An established network of relationships across the entertainment industry is strongly preferred.
• Hands‑on experience using AI tools within your discipline — able to speak to specific tools used, workflow integration, and measurable business impact — with a drive to continuously experiment with and apply emerging AI capabilities.

Special Work Conditions

• Travel required 25% of time
• Sedentary – Involves sitting most of the time but may involve walking or standing for brief periods of time. Some positions may entail exerting up to 15 lbs. of force occasionally and/or a negligible amount of force to lift, carry, push, or pull.
• #LI-AL1
• #LI-HYBRID

We take care of our people.

When you join Cast & Crew, you're backed by a benefits package built around what matters most. From comprehensive medical, dental, and vision coverage, to a 401(k) match, generous PTO, paid parental leave, health and wellness programs, tuition reimbursement, and employee discounts. We’re committed to helping you thrive, professionally, and personally.

Benefits are subject to eligibility requirements.

Cast & Crew is an equal opportunity employer committed to hiring a diverse workforce and sustaining an inclusive culture. It is our policy to provide equal employment opportunities to all individuals based on job-related qualifications and ability to perform a job, without regard to age, gender, gender identity, sexual orientation, race, color, religion, creed, national origin, disability, genetic information, veteran status, citizenship or marital status, and to maintain a non-discriminatory environment free from intimidation, harassment or bias based upon these grounds.

CA residents

Compensation is commensurate with various factors including, but not limited to, relevant experience, qualifications, skills, training, licensure, certifications, geographic cost of labor, and other business and organizational needs. Compensation range for candidates in other locations may differ based on the cost of labor in that location. The compensation range for this position is: $239,000.00 - $273,000.00 per year.