The First Assignment: Building Your Marketing Strategy

This is Part 2 of a 16-part series on building your AI VP of Marketing with Claude Cowork. Previous: The Hire: Setting Up Your AI Marketing Executive | Next: You're Still the Boss: Human Accountability for AI Outputs

Your VP of Marketing has a desk and a name badge. They know your company name, your industry, your brand voice, your target audience, and your top three goals. That is roughly what a new hire knows after reading the offer letter and skimming the company website.

No executive produces useful strategy from that alone. Before you hand over a real assignment, your VP needs the context that separates generic advice from advice that fits your business. Who are you competing against? What marketing have you tried? What is actually broken right now?

Along the way, you will meet Cowork's Memory feature, which means the VP retains what it learns and gets sharper with every conversation.

Deepening the Brief

The CLAUDE.md you built in Article 1 covers the essentials. It tells your VP what the company does and who it serves. That is the foundation, but strategy requires a different layer of information — the kind that lives in your head and rarely makes it into a document.

Your VP needs to understand five things before it can produce anything useful:

• Competitive environment. Who are the top three to five competitors? What do they do well? Where are they weak? If you sell accounting software for freelancers, your VP needs to know that Competitor A dominates on pricing while Competitor B owns the "easy to use" message.
• Current channels. What marketing are you actually doing today? Social media accounts, email lists, paid ads, referral programs — and honestly, which ones are working and which are just running on autopilot.
• Pain points. The specific problems keeping you up at night. Not "we need more leads" — but leads from where, for what, and why the current approach is failing. The more specific you are, the more useful the strategy will be.
• Budget and capacity. Both money and time. A strategy that assumes you have a designer, a copywriter, and ten hours a week for marketing is useless if you have four hundred dollars a month and Tuesday afternoons.
• Timeline pressures. A product launch in six weeks, a seasonal sales window, a conference in August — anything that should shape what gets prioritized first.

You could type all of this into your CLAUDE.md directly. But there is a faster approach: let the VP interview you. Paste the following prompt into your Cowork project and answer the questions it asks.

I need you to interview me so you can build a complete picture of our marketing situation. Ask me these questions one at a time — wait for my answer before moving to the next one.

1. Who are our top 3-5 competitors? For each one, what do they do better than us at marketing, and where are they weak?
2. What marketing channels are we currently using? For each one, is it working, underperforming, or something we just set up?
3. What are the 2-3 biggest marketing problems we face right now? Be specific — not "we need more leads" but what exactly is broken.
4. What is our realistic monthly marketing budget? Include both money and time (hours per week you can personally spend on marketing).
5. Are there any upcoming deadlines, launches, or events that should shape our priorities in the next 90 days?

After I answer all five, summarize what you learned and add it to your knowledge of our company. Then tell me if you see any gaps I should fill in.

Answer honestly. If your budget is two hundred dollars a month and four hours a week, say that. A strategy built on a fictional budget wastes everyone's time. If you have no competitors that you know of, say that too — your VP will help you identify them.

Once the interview is done, your VP has a working picture of the business. Not perfect, not complete, but enough to produce a first draft that is grounded in reality rather than templates.

The Strategy Assignment

You are going to ask your VP to produce a marketing strategy brief — the kind of document a real marketing executive would present in their first month.

The difference between a useful strategy request and a useless one comes down to structure. Vague asks get vague answers.

Bad: "Make me a marketing plan."

That gives your VP nothing to work with. It does not know what format you want, what time horizon matters, or which decisions you need it to make. You will get a generic ten-page document that could apply to any business.

Also bad: "Give me a comprehensive marketing strategy covering all channels, audiences, messaging, branding, competitive positioning, and quarterly goals."

That is not structure — it is a wish list. When everything is a priority, nothing is. Your VP will try to cover all of it and do none of it well.

Good: a request that specifies the deliverable, names the exact components you need, and states the constraints up front. You are telling your VP what the document should contain and what the boundaries are. Here is the prompt to paste into your Cowork project:

Using everything you know about our company, competitors, channels, budget, and timeline, produce a marketing strategy brief with these four sections:

AUDIENCE SEGMENTS
Define 2-3 distinct audience segments we should target. For each one, give me:
- A specific description (not just "small businesses" — tell me the job title, company size, industry, and what problem they are trying to solve)
- Why this segment is a priority for us right now
- How large this segment is relative to the others

MESSAGING PILLARS
For each audience segment, define 3-5 messaging pillars — the core themes our marketing should hit. Each pillar needs:
- A one-sentence summary
- Why this message resonates with this specific segment
- One example of how it would show up in practice (a headline, a social post, an email subject line)

CHANNEL STRATEGY
For each audience segment, recommend which marketing channels to use. For each channel:
- Why this channel reaches this segment
- What kind of content works on this channel
- How often we should post or publish, given our budget and time constraints
- What success looks like in 90 days (specific metrics, not "increased engagement")

90-DAY ACTION PLAN
Give me a prioritized list of actions for the next 90 days. For each action:
- What it is
- Which segment and channel it serves
- How long it will take
- What I need to do vs. what you can help me produce

Be realistic about our budget and time constraints. I would rather have a plan I can actually execute than an ambitious one I will abandon in week three.

Each section exists for a reason. Audience segments force specificity — you cannot market to everyone effectively, and your VP needs to commit to who matters most right now. Messaging pillars create consistency — once you agree on the three themes that matter for each audience, every piece of content has a clear job. Channel strategy prevents the spray-and-pray approach where you post everywhere and measure nothing. The 90-day plan turns strategy into action with deadlines you can actually hit.

The final line — "be realistic about our budget and time constraints" — is the most important sentence in the entire prompt. It anchors the output to your real situation. Without it, you get recommendations built for a team of five with a ten-thousand-dollar monthly budget.

Review the Deliverable

Your VP will produce a strategy brief. It will look polished and thorough. Your job now is to read it like a skeptical business owner, not an impressed first-time user.

Start with the audience segments. Are they specific enough to actually target? "Small business owners" is not a segment — it describes half the economy. "B2B SaaS founders with 10-50 employees who have outgrown word-of-mouth referrals and need a repeatable pipeline" is a segment. You can find those people, write for them, and measure whether your marketing reaches them. If your VP gave you broad segments, push back.

Check the messaging pillars next. Each segment should have distinct messaging. If all three segments get the same five pillars, the segmentation is not doing its job. The messaging for a startup founder should sound different from the messaging for an enterprise procurement manager. They have different problems, different vocabularies, and different triggers.

Look at the channel strategy with your budget in mind. If your VP recommended a YouTube channel, a podcast, a weekly newsletter, daily LinkedIn posts, and a paid Google Ads campaign — and you have four hours a week — the strategy is fiction. Two channels executed well will outperform five channels done poorly. Tell your VP to cut it down.

Finally, check the 90-day plan for specificity. "Build social media presence" is not an action item. "Publish two LinkedIn posts per week targeting the SaaS founder segment using the 'operational efficiency' messaging pillar" is an action item. You can do it on Tuesday. You can check whether you did it on Wednesday.

Give your feedback directly, the same way you would talk to a real executive who brought you a first draft.

Good start, but I need changes:

1. The "growing businesses" segment is too broad. Split it into two: service businesses with 5-20 employees, and SaaS companies with 10-50 employees. They have completely different buying patterns.

2. The channel strategy has too many channels. I can commit to LinkedIn and email. Drop the rest for now — we can add channels in Q3 if these two are working.

3. The 90-day plan needs specific weekly milestones. Break it into Month 1, Month 2, Month 3 with concrete deliverables for each.

This is not a one-shot process. You are refining a document together. Most strategy briefs take two or three rounds of feedback before they are solid. That is normal — it is how you would work with a human VP too.

Here is what a typical iteration cycle looks like. Round one: the VP produces a complete brief. You read it and find three problems — one segment too broad, the channel strategy overcommitted, and the 90-day plan missing weekly milestones. You send feedback like the example above. Round two: the VP comes back with a tighter version. Now you notice the messaging pillars for Segment A and Segment B sound too similar. You push back on that. Round three: the segments are distinct, the channels are realistic, and the plan has dates. You approve it.

Three rounds is not a failure. It is the process working. Each round sharpens the VP's understanding of what you actually need. And because of Memory (which you will meet in the next section), those refinements carry forward — the VP will not make the same assumptions again.

Meet Memory

Every decision you just made — the audience segments you approved, the messaging pillars you refined, the channels you chose, the 90-day plan you signed off on — your VP remembers all of it.

Cowork's Memory feature works in the background. As you and your VP discuss strategy, make decisions, and refine documents, Cowork captures the important details automatically. You do not need to save anything manually. You do not need to copy key decisions into a separate document. The VP retains what matters and references it in future conversations.

Your VP builds a cumulative understanding of your business. The strategy brief is not just a document — it is the foundation that shapes everything your VP produces from this point forward.

When you ask your VP to write a blog post next month, it will write for the audience segments you defined today. When you ask it to draft an email campaign, it will use the messaging pillars you approved. When you ask it to prioritize a new initiative, it will weigh it against the 90-day plan you built together.

Here is a concrete example of Memory in action. Today, you tell your VP that your audience segments are "SaaS founders with 10-50 employees" and "service business owners with 5-20 staff." Next week, you open Cowork and say: "Draft a LinkedIn post promoting our new onboarding feature." You do not re-explain who the audience is. The VP already knows. It writes the post targeting SaaS founders, uses the messaging pillars you approved, and keeps the tone consistent with the brand voice from your CLAUDE.md. That is Memory working across every conversation in this project.

Memory also means your VP improves over time. After you publish a few blog posts and see which ones get traction, you tell your VP what worked. It adjusts its understanding. After a quarter of email campaigns, it knows which subject lines your audience responds to. The VP you have in three months will be meaningfully sharper than the one you have today — not because the technology changed, but because it accumulated real knowledge about your business.

What is Next

Before you start handing your VP more assignments or building marketing tools, there is something you need to establish first: you are accountable for everything your VP produces. Article 3 builds the review and approval framework that keeps you in control.

This is Part 2 of 16 in the Your AI VP of Marketing series. Previous: The Hire | Next: You're Still the Boss