Founding Head of Sales

Join to apply for the Founding Head of Sales role at Flawless

Join to apply for the Founding Head of Sales role at Flawless

"The AI company that's revolutionizing Hollywood"
Flawless is transforming Hollywood with assistive AI. Our tools empower filmmakers to edit, localize, and refine performances while preserving artistic intent.
Designed to support, not replace, artists, our technology expands what is possible on screen and gives creators freedom to tell stories with greater impact and reach audiences in new ways. From enabling seamless multilingual releases to eliminating the need for costly reshoots, Flawless solves critical challenges that slow down productions and limit distribution.
We are also setting the standard for ethical AI in entertainment. Our Artistic Rights Treasury (A.R.T.) is a rights management solution that protects artists and rights holders, ensuring that innovation moves forward with transparency and respect for creative ownership.
Reports to:
Alex Ford - Chief of Growth
What we are looking for:
We’re seeking an entrepreneurial, driven sales leader with a proven track record of closing complex enterprise deals, ideally in the Media & Entertainment sector. You’re both a strategist and a player-coach: equally comfortable engaging senior executives at the C-suite and mentoring a growing team of sales reps. The ideal candidate combines industry credibility, B2B SaaS expertise, and startup grit to build a high-performing sales organization from the ground up.
In this role, you will be the architect and owner of the entire sales function , responsible for developing Flawless AI’s go-to-market strategy and executing on ambitious revenue targets.
As our first senior Sales leader, you will act as a “player-coach ” – closing enterprise deals with major studios and content creators yourself while recruiting, mentoring, and managing a team of junior sales reps (BDRs/SDRs and AEs) to scale our reach.
This is a high-impact leadership role that requires deep familiarity with B2B enterprise sales in a SaaS/tech startup environment and offers a unique chance to own the sales function from the ground up at a company that is redefining how movies and content are produced worldwide.
Responsibilities:

• Develop and execute a comprehensive sales strategy to drive revenue growth in the Media & Entertainment vertical
• Define target market segments, refine our value proposition, and establish scalable sales processes and KPIs
• Build and lead a results-driven, accountable, high-performance sales culture
• Prospect and engage major film studios, streamers, and production companies
• Lead enterprise sales cycles end-to-end, from prospecting and demos to negotiation and close
• Foster strong C-level relationships and act as the trusted advisor to strategic accounts
• Hire, mentor, and manage a team of BDRs and AEs to scale go-to-market efforts
• Establish pipeline management and forecasting discipline with CRM tools and analytics
• Collaborate cross-functionally with marketing, product, and engineering to represent the customer’s voice and shape market fit
  

Qualifications:
Must haves

• Strong sales track record of consistently exceeding quotas and delivering against ambitious revenue targets
• 5+ years of successful B2B enterprise sales experience in SaaS/enterprise software
• Proven track record of closing large, complex deals (6–7 figure contracts) with major enterprise clients
• Strong understanding of Media & Entertainment workflows and post-production processes
• Demonstrated experience building and managing sales teams (hiring, coaching, performance management)
• Deep knowledge of enterprise sales methodologies (e.g. MEDDIC, Challenger Sale, SPIN) and structured sales processes
• Exceptional communication, presentation, and negotiation skills with ability to engage both creatives and executives
• Entrepreneurial mindset with ability to thrive in a fast-paced, high-growth startup environment
  

Bonus

• Existing network and relationships within Hollywood studios, OTT platforms, or production companies
• Experience in AI, video technology, or content localization
  

Interview Process:
At Flawless, our team and interview process want to help you show your best self. We’ll dive into past projects and simulate working together.
Our interview process is three rounds with some casual Zoom (or in-person) coffee in between to get to know each other:

• Recruiting Screen: 30-45 minute call with our recruiting team (We want to discuss your interests and motivations as well as the practical details and make sure that Flawless would be a good fit for you)
• Hiring Manager Screen: 45-60 minute
• Skills interviews: 1-2 sessions digging into core skills for the role. Here you will likely meet with some of our leadership team as well as peers from other departments
• Team Interview: :2 hours onsite Interview where you will meet variety of your potential future colleagues
  

Your Recruiter and hiring manager will be your main point of contact and prepare you for interviews. You’ll meet 4 to 6 people from across the business. (We make sure that you have time in each interview to ask them questions). If we don’t give an offer, we’ll provide feedback!
Why work at Flawless?
You will be working in an environment based on trust, autonomy and collaboration, and this is a great opportunity for someone who wants to be part of a growing company in its most exciting stage of development. You can play a part in shaping the future of a company that’s caring, creative and collaborative.
In addition to this, you'll also receive:

• Autonomy
• A hybrid working environment
• Competitive Salary
• Stock Options
  

I don’t meet all the listed requirements—should I still apply?
Absolutely! Research shows that women and underrepresented groups often hesitate to apply unless they meet every qualification, but at Flawless, we actively work to break down those barriers. We believe diverse perspectives, experiences, and backgrounds make us stronger, and we are committed to supporting and elevating underrepresented talent. If you're excited about the role, share our values, and believe you can contribute meaningfully, we encourage you to apply—even if you don’t meet every single requirement. Your unique skills and perspective matter, and we’d love to hear from you ️

Seniority level

• Seniority level

  Executive

Employment type

• Employment type

  Full-time

Job function

• Job function

  Sales and Business Development

• Industries

  Software Development

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