Sherwood Software Solutions
Careers

Work with Sherwood.

We build AI systems that run real parts of a business: websites, assistants, outreach, and content. We are building a team of independent Product Specialists who bring those systems to the businesses that need them.

Open positions

Product Specialist

Independent contractor · Remote

Product Specialists are independent contractors who introduce businesses to Sherwood's AI systems, run demonstrations, and guide each prospect from first conversation to a working system.

The opportunity

  • Present Sherwood's websites, assistants, and Repertoire to businesses.
  • Run live demonstrations and match each business to the right system.
  • Access to Sherwood's CRM, sales tools, demo materials, and product training.
  • A flexible, remote role, with optional in-person coaching and meetups in the Westlake Village area.
  • Commission on every client you bring to Sherwood.

What we look for

  • A proven record in sales, ideally software, technology, or services sold to businesses.
  • Comfort leading a conversation with an owner or executive.
  • Clear, honest communication. We describe what we do and never promise results we cannot control.
  • Curiosity about AI and the willingness to learn our products in depth.

This is an independent contractor (1099), commission-only opportunity. Full details are discussed directly with candidates.

Apply for this role
Apply

Apply below, or email john@sherwoodsoftware.ai with your resume and a short note about your sales experience.

Are you comfortable with a commission-only, independent contractor (1099) arrangement? *
Are you legally authorized to work in the United States? *
Do you currently live in California? *

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