Freelance Director of Sales

Posted 2 days ago

playbookJacksonville (FL)

Sales Representatives of Services, Except Advertising, Insurance, Financial Services, and Travel Custom Computer Programming Services

SENIORITY

Manager

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About the role

Company Description: Playbook is an AI-native Digital Asset Management (DAM) and Product Information Management (PIM) platform built to be the organized home for all creative work. By combining Pinterest-simple design with Enterprise-grade automation, Playbook streamlines how teams share and collaborate on visual projects. Our proprietary AI-driven engine automatically imports, tags, and categorizes entire media libraries in minutes - reclaiming valuable hours for creative and marketing professionals. Today, Playbook empowers 2.5 million creatives and 10,000 teams worldwide, ranging from boutique agencies and e-commerce brands to Global Enterprise marketing and leaders in Games, Marketing, Media, and Entertainment.

Role Description: This is a remote contract role for a Director of Sales Consultant. Earn 100% of every first-year contract you close - paid as invoices collect - plus 10% of the contract value in year two. No cap. No ceiling.

What you'll do:

Identify and close deals with creative teams, agencies, and brands that need an AI digital asset management solution
Run your own outreach and pipeline using Playbook's sales materials and live demo environment
Represent Playbook professionally - you're the first impression for many of our future customers
Who this is forB2B or SaaS sales and marketing professionals comfortable with consultative selling
People with existing networks in creative, marketing, media, or agency spaces
Self-starters who thrive without a quota, a manager, or a script
Must reside in the United StatesMust be a Playbook user
What Playbook provides
Full sales collateral - decks, one-pagers, demo access, and a dedicated onboarding call
Commission paid as invoices collect - no waiting 90 days after close
Direct access to the founding team for questions, product deep-dives, and deal support
How commissions are paid

You earn 100% of the first-year contract value, paid to you as invoices are collected - monthly or quarterly depending on the customer's billing schedule. Year 2 renewals pay a 10% residual on the contract value, automatically. No chasing payments. No 90-day holds. To apply, please send your resume directly to. We prefer email as LinkedIn messages often get lost in the noise.

Before you apply

Applying takes about a minute. These four things decide how fast it moves after that.

Your profile is current

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Two examples you can talk through

Not a portfolio — just two pieces of work where you can explain the decisions and what you'd change.

A number in mind

What you're on now and what would make you move. We negotiate better when we know both.

Your notice period

Employers plan around it, and it's the question that stalls offers most often.

Once you apply, someone reads it and calls you before anything reaches the employer — usually within two working days.