EP42: Diary of my first 90 days as a fractional CMO

When I accepted a fractional CMO role in mid-February, I knew the first 90 days would be make-or-break. Not just for the company, but for determining whether this was the right fit for both of us.

Now that I’m coming up on my 90-day mark, I wanted to document my process, approach, and key learnings. This isn’t just for other fractional executives or founders considering hiring one—it’s also my own diary of what worked, what didn’t, and what I’d do differently next time.

The reality check: Why 90 days matter

I’m always hesitant to shout from the rooftops about joining a new company until I’ve completed those critical first 90 days. That’s when you really know if it’s the right fit. It’s when you understand whether your approach aligns with the company’s needs, culture, and leadership style.

I joined mid-February, navigated through March and April, and I’m recording this in May. Three full months of real-world experience that I can actually analyze and learn from.

My framework: People, Processes, Tools, and Data

When I think about what a CMO does at an early-stage company, it boils down to four critical areas:

• People: Do we have the right people in the right seats?
• Processes: Do we have clear ways to accomplish the work?
• Strategy: Do we understand what the right work actually is?
• Operations: Do we have solid budgets, performance tracking, and data flows?

This framework guided everything I did in those first 90 days.

Month One: The information download

Weeks 1-2: Getting Access to Everything

The first two weeks were pure information gathering. I needed access to all the tools, folders, artifacts, and “marketing graveyards”—you know, those dusty persona documents from three years ago that everyone forgot existed.

I approached this with healthy skepticism. Not everything was going to be relevant, but I needed to understand where we came from to know where we were going. The team was transparent about what was still useful versus what was outdated.

During this phase, I was also digging into the technical side:

• How do our systems talk to each other?
• What are we measuring and tracking?
• How do we define key metrics like “trial” or “conversion”?

Every company has its own language for these things, and understanding both the business definitions and technical implementations was crucial.

Weeks 3-4: Creating the Foundation

By the third and fourth week, I was focused on creating two critical artifacts:

The Marketing Strategy Document: This outlined our approach for the rest of the year (initially just the next two quarters, since I wanted to test my assumptions before committing to longer-term plans).

The CMO’s Mandate: This was my constitution—a document that clearly outlined:

• My areas of focus
• How to work with me
• What everyone could expect from me
• Which territories I’d be investigating

I chose to create a document rather than a presentation because it felt more concrete and permanent. I even recorded a Loom video to walk the team through it, banking on their curiosity to engage with the content.

Month Two: Getting the right people in the right seats

Month two was all about execution and alignment. We needed to find a paid ads agency and hire someone to own SEO and content marketing. But more importantly, I needed to understand our work paths—not just processes, but how things actually got done and who was doing them.

The Financial Deep Dive

One of the biggest investments of time was getting our budget and goals crystal clear. Working closely with the CEO (who also wore the CFO hat), we dove deep into three critical areas:

• Forecasting: Where we think we’re going financially based on past performance
• Budgeting: How much we can spend based on cash on hand and expected revenue
• Planning: Working backward from our target to understand what we need to hit

This distinction was crucial. Planning is different from forecasting because you’re backing into goals rather than projecting forward. It’s a completely different mental exercise.

We spent 2-3 weeks getting aligned on this, with constant iterations as we remembered forgotten variables or uncovered new considerations. But this alignment was essential—the CMO and CFO really do need to be best friends.

Identifying Gaps and Opportunities

Throughout this process, I was constantly looking for gaps in four categories:

“Setting Cash on Fire” Moments: High-priority issues like extremely low conversion rates where we’re wasting money on traffic that doesn’t convert.

Future Problems: Issues that aren’t critical now but will become painful if ignored.

Nice-to-Haves: Positive impact items that aren’t high priority.

Opportunities: Things we could leverage that we’re currently missing, like better content alignment or new program possibilities (they’d never done ABM, for example).

Month Three: Streamlining and executing

Month three was when everything came together. My mantra became “get executors executing.”

Building the Marketing Hub

One of the first operational changes was creating a centralized marketing hub in Notion. Everything was spread across Google Drive without a clear source of truth. I didn’t care what task management system people used individually, but I needed marketing under one umbrella with clear links to all our artifacts.

Establishing Rhythms

I also established a weekly marketing meeting cadence and streamlined our one-on-one processes. Instead of repeating the same information to everyone individually, we could share updates once a week in a group setting.

For a remote team, you need clear boundaries about where information goes, when to have meetings versus when to use Slack, and where to capture ideas—whether in chat or a proper database.

Cross-Team Alignment

The third month was also when I started interfacing more with product and sales teams. The first two months were about understanding my own team; month three was about understanding how we work with others to accomplish the company’s overall mission.

I could already feel the shape of Q3 and Q4 taking form. My business coach always says to keep your eye “two weeks out, two months out, and two quarters out”—and I was already seeing opportunities for activation work in Q3.

What’s next: Beyond the 90-day mark

Moving forward, my focus shifts to:

Streamlining and Gap-Filling: We have some resource gaps and I need to figure out how to cover those bases within our budget constraints.

Pivoting Two Ships: There are a couple of strategic directions that need adjustment. My job isn’t to execute the work myself, but to get executors aligned and executing in the new direction.

Cross-Team Collaboration: Deeper work with product on activation opportunities and with sales on campaign collaboration. I want to get to a place where working together feels like play rather than something hard, unknown, and scary.

Key learnings and reflections

What Worked Well

• Document Over Deck: The CMO’s Mandate as a written document was more accessible and concrete than a presentation would have been.
• Healthy Skepticism: Not accepting everything at face value while still respecting the work that came before.
• Financial Alignment First: Getting aligned on budgets and goals before diving into tactical execution.
• Clear Communication Boundaries: Establishing where information lives and how we share it across a remote team.

What I’d Do Differently

• Earlier Financial Context: I might have done the financial planning work before the initial strategy document (although in this particular case I was happy to have context before diving into financials). 
• Faster Resource Gap Identification: Some resource gaps became apparent early but took time to address properly.

The Ongoing Challenge

The biggest ongoing challenge is that gaps and opportunities continue to surface over time. You can’t catch everything in the first 90 days, and that’s okay. The key is identifying the most mission-critical issues and addressing those first.

The bottom line

Those first 90 days as a fractional CMO are intense, but they’re also energizing. Every day brings new challenges to coordinate and problems to solve. The key is having a clear framework for how you approach the role and maintaining focus on what matters most: getting the right people executing the right work in the right direction.

For founders considering a fractional CMO: be prepared for someone who will dig into everything from your technical integrations to your budget planning. The best fractional executives don’t just optimize marketing channels—they optimize your entire go-to-market engine.

For other fractional executives: document your process. You’ll be surprised how much you learn about your own approach when you’re forced to articulate it clearly.

And for me? Well, I’m looking forward to the next 90 days and seeing how these ships we’re pivoting actually perform in the market.

If you’re considering bringing in fractional marketing leadership for your SaaS company, I’d love to hear about your challenges and goals. The first 90 days are just the beginning—the real work starts when you can shift from setup to acceleration.