VP, Sales, Live Entertainment

401 Cast & Crew LLC; California; Hybrid; USD 239,000 - 273,000; Full time

Benefits offered by this job

Medical, dental, vision coverage

401(k) match

Paid time off

Parental leave

Tuition reimbursement

Employee discounts

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, secure, and cultivate partnerships while guiding the sales team to meet revenue targets and deliver outstanding client outcomes.

This senior leadership role requires 12–15 years in sales with deep industry experience, executive presence, and the ability to lead cross-functional initiatives.

Qualifications

• Proven senior sales leadership experience in live entertainment and payroll services.
• Track record of exceeding revenue targets and growing pipelines.
• Ability to translate market intelligence into go-to-market plans.

Responsibilities

• Define and execute the sales strategy; manage the sales cycle from prospecting to closure.
• Oversee sales operations and end-to-end processes including lead gen, proposals, negotiations, and post-sales support.
• Develop and maintain key client relationships; expand the customer base and revenue.

Skills

Entertainment payroll

Sales leadership

Strategic planning

Executive negotiation

Stakeholder management

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

Your personal information may be collected in connection with certain services provided by Cast & Crew or its affiliated companies. A summary of your California privacy rights can be found at: https://www.castandcrew.com/privacy-policy/

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.

We grew from a modest small business in 1976 to be the premiere provider of entertainment technology and solutions, staying true to our mission of modernizing content production and leading the digital transformation within the industry. Our cloud-based solutions and industry expertise help streamline the entire production lifecycle and have revolutionized how content is made. We now have a global workforce across a host of storied brands, spanning all areas of produced and live entertainment, from film, television, streaming, to advertising, live events, and short-form.

Our company is committed to a culture of encouraging unique perspectives and backgrounds and to ensure growth and opportunities are available for all. Come join our team of talent that helps make magic happen. #OneCastOneCrew