Role type: Project-based, retainer, fractional, or long-term contractor
Level: Mid-level to senior specialists
Location: Remote, hybrid, or San Juan-based depending on the work
Path: Preferred contractor, long-term partner, or possible future employment depending on fit

Specialists who can work inside strategy.

TELL ME MORE® works with specialist contractors when we need deeper expertise, additional production capacity, or technical support beyond our internal team.

But we are not looking for interchangeable freelancers. We work with the same contractors for years.

Our specialists can plug into strategic work, understand the purpose behind the task, communicate clearly, and help us make the final product better.

Our internal team handles much of the strategy, UX, content, design direction, AI-assisted prototyping, and web production. But we regularly need excellent specialists in areas like development, integrations, analytics, QA, video, motion, automation, SEO, and design execution.

The best TMM contractors are not passive order-takers.

They ask:

Then they do excellent work.

We are especially interested in contractors with expertise in:

Advanced WordPress development

• Custom WordPress builds
• Custom themes and blocks
• Advanced animations
• Performance optimization
• Technical troubleshooting
• Git/GitHub workflows
• Plugin evaluation and customization
• Security and maintainability

CRM, integrations, and technical systems

• Salesforce integrations
• HubSpot integrations
• API connections
• Marketing automation
• Lead routing
• Form systems
• Zapier, Make, n8n, or custom automation
• Data integrity and QA

Analytics, tracking, and reporting

• GA4
• Google Tag Manager
• Looker Studio
• Conversion tracking
• Event tracking
• Heatmap/session-recording tools
• SEO and content reporting
• Dashboard design
• Attribution troubleshooting

QA and technical review

• Website QA
• Cross-browser testing
• Mobile/responsive testing
• Accessibility review
• Form testing
• Content QA
• SEO QA
• Pre-launch and post-launch testing
• Regression testing

SEO, AEO, and LLM visibility

• Technical SEO
• Content audits
• Entity optimization
• Schema
• Internal linking
• SERP analysis
• AI search visibility
• LLM citation and retrieval research
• Content performance analysis

Video, motion, and AI-assisted creative production

• Video editing
• Motion graphics
• Short-form social video
• YouTube production
• AI video tools
• AI image generation
• Sound design
• Visual storytelling
• Repurposing long-form content into clips

Design and visual systems

• Web design
• Figma
• Brand systems
• Presentation design
• Sales decks
• SOQs
• Collateral
• AI-assisted design exploration
• Visual research and avatar development

Writing, research, and content production

• Long-form content
• Expert interviews
• Transcript synthesis
• Thought leadership
• SEO/AEO content
• Case studies
• Sales copy
• Executive ghostwriting
• Video scripts
• Research-heavy writing

What we expect from contractors

We value contractors who:

• Communicate clearly.
• Hit deadlines.
• Ask good questions early.
• Understand the strategic context of the work.
• Are comfortable working with a small, high-trust team.
• Can receive feedback without drama.
• Document their work.
• Use AI where appropriate to improve speed and quality.
• Care about the final result, not just their assigned portion.
• Flag risks before they become problems.
• Know when to move fast and when to slow down.

We do not expect contractors to be available at all times. But we do expect clarity, reliability, and professional communication.

You may be a fit if

• You are excellent at a specific craft.
• You prefer high-quality work over high-volume churn.
• You enjoy working with strategic teams.
• You can operate without excessive hand-holding.
• You are comfortable with AI tools or actively learning them.
• You like projects where the thinking matters.
• You want long-term relationships, not one-off chaos.
• You are willing to challenge an approach respectfully when you see a better solution.

You are probably not a fit if

• You only want fully defined tickets with no context.
• You disappear when things get complicated.
• You resist documentation.
• You dislike feedback.
• You are careless with details.
• You are slow to communicate.
• You overpromise and underdeliver.
• You treat AI as a threat rather than a tool.
• You do not care how your work fits into the client’s larger strategy.

How we work with contractors

Depending on the project, we may work with contractors through:

• Fixed-scope projects
• Hourly work
• Monthly retainers
• Ongoing support relationships
• White-label collaboration
• Specialist oversight of AI-assisted production
• Technical review and QA
• Emergency support when a project requires deeper expertise

Our goal is to build a trusted bench of people we can return to again and again.

How to apply

Send an email to Careers@TellMeMore.co with:

Optional Loom prompt:

“Walk us through one project where you solved a problem, not just completed a task.”