How Do We Measure Success in 90 Days?
The first 90 days as a fractional CMO at a new company aren't about generating massive revenue or building a new marketing team. They're about building the foundation that makes everything else possible. They're about strategy, alignment, and clarity. If we nail those things in the first 90 days, the growth comes naturally.
Here's exactly what a successful 90 days looks like and how we measure it.
WEEKS 1 THROUGH 2: LISTENING AND DISCOVERY
The first two weeks are about understanding the business deeply. I'm not coming in with a predetermined playbook. I'm coming in to learn.
During week one, I'm meeting with every executive on your leadership team. I'm sitting down with the CEO, the CFO, the head of sales, the head of product, your head of customer success if you have one. I'm asking them the same core questions: What are your biggest challenges? What does success look like for the business over the next year? What's broken in marketing from your perspective? What are you worried about? Where do you think we're leaving money on the table?
I'm also doing a full audit of your current marketing. I'm looking at your website. I'm reviewing your messaging. I'm checking out your competitor positioning. I'm looking at your current campaigns, your email programs, your paid advertising, your social media. I'm reading recent case studies and whitepapers. I'm looking at your sales collateral. I'm trying to understand what you've been doing and why.
By the end of week one, I have a clear picture of how every executive sees the business and what they think marketing's role should be.
In week two, I'm doing customer discovery. I'm talking to your sales team about what customers actually care about and what objections they're hearing. I'm talking to your customer success team about what's resonating with customers and what's not. I'm reviewing customer feedback, surveys, and support tickets. I'm looking at churn data if you have it. I'm trying to understand what your customers actually need and why they chose to buy from you.
Success metric for weeks one and two: I've completed at least eight executive interviews, I've done a full audit of existing marketing assets, and I've talked to at least five members of your sales or customer success team.
WEEKS 3 THROUGH 4: IDENTIFYING THE CORE ISSUES
By the third week, I'm starting to see patterns. I'm seeing where any misalignment is. I'm seeing where the messaging is off and where it is working well. I'm seeing where the strategy doesn't match what the market actually wants.
During weeks three and four, I'm interviewing your marketing team (if you have one) and any agencies or freelancers you're working with. I'm understanding what they think the problems are and what constraints they're operating under. I'm also doing a deep dive on your revenue. I'm looking at where customers are coming from. I'm looking at the path to sale. I'm looking at what's working and what's not in your current go-to-market approach.
I'm also starting to synthesize everything I've learned. I'm asking myself: What is this company actually good at? What is the real market opportunity? What is your competitive advantage? Why should customers buy from you instead of someone else? Are those messages being communicated clearly?
Success metric for weeks three and four: I've completed interviews with your internal marketing team and any external partners, I've fully analyzed your revenue sources and customer acquisition channels, and I've started identifying the top three strategic issues facing the business.
WEEKS 5 THROUGH 8: STRATEGY DEVELOPMENT
By week five, I'm moving from discovery to strategy. I'm working on defining or refining your go-to-market strategy. This is the core of what we're doing. The strategy work includes several components.
First, we're getting clear on positioning. What is your company? Who is it for? Why should they care? What makes you different? This sounds simple, but most companies aren't actually clear on this. I'm documenting this in a positioning statement that every executive agrees with.
Second, we're defining your target customer. We're being specific. Not just "mid-market SaaS companies" but "mid-market SaaS companies with more than 100 employees trying to scale sales." We're defining the person who benefits most from what you sell and the specific problem you solve for them.
Third, we're mapping your go-to-market motion. How do customers find you? How do you reach them? Are you inbound, outbound, or both? Are you selling through sales or self-serve? Are you doing content marketing, paid advertising, partnerships, direct sales, or some combination? We're being intentional about this instead of just doing what you've always done.
Fourth, we're defining your customer acquisition strategy. Where are your ideal customers today? How do we reach them most efficiently? What channels make the most sense? Where should we be investing money and resources?
Fifth, we're talking about messaging and narrative. What's the story you're telling? What problem are you solving? What does success look like for your customers? What are the key talking points that show why you're different?
By week seven, I've got a draft strategy document that outlines all of this. I'm presenting it to your executive team. We're debating it. We're refining it. We're making sure everyone is aligned.
During week eight, we're locking in the strategy. Everyone agrees on positioning, target customer, go-to-market motion, customer acquisition approach, and key messaging.
Success metrics for weeks five through eight: I've completed a positioning statement that all executives agree with, I've defined your target customer profile with specific criteria, I've created a go-to-market strategy document that outlines your approach across all channels, and we've had at least two strategy review sessions with your leadership team.
WEEKS 9 THROUGH 12: IMPLEMENTATION PLANNING AND QUICK WINS
Once the strategy is locked, we're planning how to execute it. Weeks nine through twelve are about creating the roadmap.
During these weeks, I'm working with your team to create a quarterly marketing plan. This plan outlines what we're going to do, in what order, who's responsible, and what success looks like. It includes campaigns, content, messaging updates, website changes, new landing pages, paid advertising tests, sales enablement work, everything.
I'm also identifying quick wins. These are things we can do in the next 30 to 60 days that will show progress and build momentum. Maybe it's updating your website's positioning. Maybe it's creating a new landing page for your biggest customer segment. Maybe it's launching a customer case study. Maybe it's starting a new content initiative or overhauling your email strategy. These aren't massive initiatives. They're strategic moves that demonstrate that the strategy is working.
I'm also putting in place measurement systems. How are we going to track whether this strategy is working? What metrics matter most? Are we tracking pipeline? Cost per acquisition? Website conversion rate? Email open rates? Sales cycle length? We're defining the metrics that actually matter for your business.
I'm meeting with your sales team during these weeks to make sure they understand the new strategy and the new messaging. I'm making sure they have the tools and collateral they need to sell effectively. If there are gaps, we're identifying them and creating a plan to fill them.
By week twelve, I've handed off a 90-day marketing plan to your team. I've documented the strategy. I've identified the quick wins. I've set up the measurement system. Everyone on your team knows what we're doing, why we're doing it, and how we're measuring success.
Success metrics for weeks nine through twelve: I've created a quarterly marketing plan that outlines specific initiatives, owners, and success metrics. I've identified at least three quick wins that can be executed in the next 30 to 60 days. I've put in place a dashboard or reporting system that tracks the key metrics for your business. I've completed a sales enablement review and documented any gaps.
THE ACTUAL MEASUREMENT AT DAY 90
So what does success actually look like at the end of 90 days? It's not a revenue number. It's not a lead generation target. It's much more foundational than that.
Success at day 90 means everyone in your organization understands your positioning and can articulate it. Success means your sales team has new messaging and tools they didn't have before. Success means you've got a documented strategy that your executive team agrees with. Success means you've implemented at least two quick wins that show the strategy is working. Success means you've got a clear quarterly plan for what marketing will focus on for the next 90 days. Success means the metrics that matter are being measured and tracked.
In practical terms, here's what we're evaluating:
Strategy clarity: Can every executive articulate your positioning, target customer, and why that customer should buy from you? If the answer is no, we didn't do the job right.
Alignment: Do your sales team, product team, customer success team, and executive team all agree on where we're going? Is there disagreement about strategy or messaging? If there's major misalignment, we didn't achieve what we needed to achieve.
Foundation: Do you have the documentation you need? A positioning statement? A customer profile? A go-to-market strategy? A quarterly plan? If these don't exist, we didn't build the foundation.
Momentum: Have we launched or updated at least two major initiatives that show the strategy is being executed? Did they get internal buy-in? Is the team feeling like we're moving in the right direction?
Measurement: Do we know what metrics matter and are we tracking them? Can I show you a dashboard or report that tells us whether the strategy is working?
Sales enablement: Has your sales team received new tools, messaging, or collateral? Are they using it? Do they understand the new direction?
If all six of those things are true at day 90, we've been successful. The business is now positioned to execute against a clear strategy with full executive alignment and the right tools and messaging to communicate that strategy internally and externally.
WHAT HAPPENS AFTER DAY 90
Once day 90 hits, we shift into execution mode. We're no longer discovering and strategizing. We're implementing the plan. We're measuring results. We're iterating based on data.
The metrics change at that point. Now we're looking at pipeline generated. Cost per acquisition. Website traffic and conversion rates. Email engagement. Sales cycle impact. Lead quality. Those are the things we measure in months four through six and beyond.
But if we've done the first 90 days right, those execution metrics take care of themselves because we've got the right strategy and everyone is aligned.
WHY 90 DAYS
You might be wondering why 90 days is the right timeframe. It's not arbitrary. It takes about four weeks to really understand a business. It takes another four weeks to develop a solid strategy. And it takes four more weeks to plan the execution and launch initial initiatives. Anything less than 90 days and you're cutting corners on strategy. Anything more and you're moving too slowly.
Ninety days is also long enough to prove the fractional model works. You can see that strategy is being developed, alignment is happening, and momentum is building. You can see whether this is working before you commit to the next phase.
When we kick off a fractional CMO engagement, the first thing I do is walk through exactly what I just outlined. I'm setting expectations about what success looks like. I'm being clear about what happens in each phase. I'm telling you how we measure it.
That way, at the end of 90 days, there's no mystery about whether it worked. We've already agreed on what success looks like. We're just checking whether we hit those marks.
Most of the time we do. Because the work is real. The strategy is real. The alignment is real. And the foundation we're building is real.
If you're at a company between five and eighty million in revenue and you need someone to come in, get your strategy right, align your team, and build the foundation for the next phase of growth, that's what I do in the first 90 days. Let's talk about whether this approach is right for you.
