Senior Strategy Lead

Role type: Full-time, fractional, contractor-to-full-time, or senior consulting relationship
Level: Senior
Location: San Juan, Puerto Rico preferred; remote/hybrid considered for exceptional candidates
Path: Potential B-Class partner path for the right person

Lead strategy. Shape the work. Help build the future of the agency.

TELL ME MORE® is looking for a senior strategic leader who can help clients see what they cannot yet see.

This is not a traditional account director role. It is not a project management role. It is not a "brand strategist" role limited to workshops and decks. And it is not an AI gimmick role.

This is a role for someone who can move between executive conversation, strategic diagnosis, positioning, messaging, web strategy, content systems, AI-assisted prototyping, and client leadership.

You should be able to sit with a CEO, founder, CMO, or leadership team and quickly understand:

What they are trying to build.
What is unclear.
What is misaligned.
What the market does not yet understand.
What the team cannot yet articulate.
What needs to be made real next.

Then you should be able to help turn that understanding into language, strategy, artifacts, and action.

At TELL ME MORE, we work with companies that need more than marketing deliverables. They need clarity. They need positioning. They need language. They need internal alignment. They need better sales materials. They need web systems that express who they are. They need content that demonstrates expertise. They need AI-first workflows that help a small team do work that used to require a much larger one.

We are looking for someone who can help lead that kind of work.

What you will do

You will help lead high-value client strategy and execution across brand, positioning, web, content, AI, and growth.

Your responsibilities may include:

Leading or co-leading executive discovery sessions, stakeholder interviews, positioning workshops, and strategic client meetings.
Translating messy conversations into clear strategic direction.
Helping clients articulate their culture, values, market position, service offerings, differentiators, and growth opportunities.
Building or overseeing positioning canvases, culture maps, messaging systems, sales narratives, website strategy, content strategy, and pitch materials.
Identifying design avatars, content models, competitive insights, and strategic references from inside and outside a client's category.
Working with TMM's team to turn strategy into websites, SOQs, pitch decks, campaigns, landing pages, video scripts, content systems, and sales enablement materials.
Using AI tools to accelerate strategic research, synthesis, ideation, prototyping, content development, design exploration, and implementation.
Helping shape AI-first workflows inside TMM.
Reviewing work for strategic quality, clarity, taste, and usefulness.
Guiding junior team members and contractors.
Supporting proposals, scopes, client renewals, and new business conversations.
Helping TMM grow without becoming a bloated, generic agency.

This role requires both altitude and craft.

You need to be able to think at the 30,000-foot level, then come back down and improve the headline, the slide, the homepage section, the positioning statement, the client memo, or the prototype.

You may be a fit if

You may be a fit if you have already demonstrated the ability to:

Lead strategic conversations with senior clients.
Understand a business quickly.
Ask penetrating questions without performing "consultant theater."
Make complex ideas simple.
Write well.
Present clearly.
Earn trust from executives.
See the relationship between culture, positioning, marketing, sales, recruiting, content, and web presence.
Use AI seriously in your workflow.
Push creative work to be sharper, clearer, and more useful.
Work with designers, developers, writers, strategists, clients, and operators.
Operate without a lot of hand-holding.
Make good decisions inside ambiguity.
Protect quality without slowing everything to a crawl.

You should have strong opinions, but not an ego that prevents collaboration.

You are probably not a fit if

This role is probably not right for you if:

You mostly want to manage accounts, not shape strategy.
You are uncomfortable challenging clients respectfully.
You rely on generic frameworks without original thought.
You are not actively using AI.
You think AI lowers quality rather than raising the ceiling of what a small team can do.
You cannot write clearly.
You cannot present your thinking clearly.
You are uncomfortable with websites, content, SEO, design, or technical production.
You need a traditional agency department structure to function.
You prefer sellin