The 90-Day Plan That Helped Me Earn C-Suite Trust at RemotePass
- Jeremiah Ajayi
- Nov 4, 2025
- 12 min read
Updated: Nov 5, 2025

Beyoncé doesn’t walk on stage and start singing. Weeks before any performance, she studies every move, rehearses every transition and makes sure the first ten seconds of the show set the tone for everything that follows.
That level of preparation is what makes her performances look effortless.
Your first 90 days as a content marketing manager work the same way. They shape how leadership sees you, how fast you earn trust, and whether your work ties back to real business impact. But most new hires rush straight into performance mode, pushing out content before they understand the story they’re meant to tell.
When I joined RemotePass, I took a different route. I spent my first month studying the product, refining our ICP, and building systems that made content run smoothly. That slow start became my advantage.
Within months, I was leading high-impact projects like the Certn-RemotePass partnership launch and earning public praise from the C-suite.

This guide is the same 30/60/90-day playbook I used to move from “new hire” to trusted strategist. It’s practical, tested and built for anyone who wants to prove the ROI of content marketing without burning out in the process.
Want a quick reference? You can download the 30/60/90 checklist as a one-page PDF to keep your first 90 days on track.
Month 1
At RemotePass, I spent the first month studying the product, talking to teams and cleaning up the mess I inherited. It wasn’t glamorous, but it built the foundation that made every later win possible.
Start by Actually Understanding the Business
Don’t rush to publish. Spend your first few weeks studying the company from the inside out.
In my case, I spent hours reading everything I could find—brand decks, OKRs, investor updates, product sheets, customer stories, even old blog posts. Each of these docs revealed something different. Investor updates told me what leadership cared about. Product sheets showed me how we sold. Customer stories showed me what people loved enough to talk about.
I also joined product demos and onboarding calls, which helped me hear how the team explained our product and how customers described their pain points. Eventually, I started spotting gaps in communication. If customers keep asking the same question, that’s a content problem waiting to be solved.
At the end of that first month, I wrote my own version of the company’s elevator pitch in plain English. If I couldn’t explain what we did in one paragraph, I knew I still didn’t understand it well enough.
Once I could explain the product clearly, I knew I was ready to write content that connects.
✅ Pro tip:
Ask three people from different teams to describe what the company does in one line. If their answers don’t sound remotely alike, that’s your first clue your messaging needs work.
Talk to Every Team You Can
In my first few weeks at RemotePass, I set up short intro calls with people across Growth, Sales, Product, Customer Success and even HR. This was because every team sees the customer from a different angle, and those perspectives are gold for a content marketer.
Sales told me where prospects were dropping off. Product team shared what users loved and what still confused them. Customer Success explained the recurring pain points that ate up their time. Growth showed me which channels actually worked. Those conversations helped me see the full picture — what messaging resonated, what content was missing and where I could make the biggest impact fast.
I kept notes from every chat in Notion and started spotting patterns. The same questions, the same gaps, the same opportunities. Before long, that doc became the starting point for my content roadmap.
✅ Pro tip:
End every intro chat with one question: If content could solve one recurring problem for your team, what would it be? You’ll leave each call with real priorities instead of vague ideas.
Audit What You Already Have Before Creating More
Before you write anything new, understand what already exists. A content audit sounds boring, but it’s how you find quick wins and avoid repeating work that didn’t move the needle.
When I joined RemotePass, I spent my second week reviewing every channel — blog, social, email, landing pages. I wanted to know what was working, what wasn’t, and what had been forgotten. I tracked which pieces drove signups, which ones people shared, and which ones got traffic but no conversions.
Numbers only tell part of the story, though. I also paid attention to tone and structure. Did our Tone of Voice (TOV) sound consistent? Did the content still reflect where the company was headed?
A lot of what ranked on Google didn’t even match how we talked about the product anymore. That disconnect became my first fix.

By the end of the audit, I knew exactly which topics deserved an update, which ones needed to be retired, and where the gaps were. That clarity saved me from guessing what to create next and gave me a solid starting point for my content roadmap.
✅ Pro tip:
Find your top five performing pieces and figure out why they worked. Was it timing, topic, or format? Once you know, repeat that pattern until it stops working.
Tighten Your ICP and Sharpen the Message
During my audit process, I realized the Ideal Customer Persona (ICP) on paper didn’t fully match the people actually buying. The docs said one thing, the CRM told another story. So I sat with the Sales team and reviewed closed-won deals, retention data and testimonials. We looked at which customers were easiest to close, which ones stuck around and which ones were the happiest. Those patterns became the base for updating our ICP.

This exercise changed how I wrote and positioned content. Instead of creating for “everyone hiring globally,” I started writing for specific people: HR leads who hated compliance work, founders who needed speed, finance heads who cared about cost efficiency. Once I got that clarity, everything clicked.
I also drafted our messaging pillars and tone notes that guided how we talked — clear, confident, and human. Later, those notes evolved into our company-wide style guide automated with a custom GPT.
✅ Pro tip
Ask your Sales team to list the top three customers they love selling to and why. Then compare that to your marketing personas. If they don’t line up, your ICP needs work.
Deliverables by the end of Month 1:
✅ Content Audit Report
✅ ICP + Messaging Brief
✅ Company-wide Style Guide
✅ Content Operations Doc (cadence, tools, ownership)
Month 2
By your second month, you should already know how the business runs and what content gaps exist.
Now it’s time to turn all that context into action by taking the steps below.
Use Data to Build a Strategy That Moves Revenue
By month two, you’ve learned enough to move from learning to building. Your goal now is simple: connect content to business impact.
Most content marketers slip here. They jump straight into creation without backing it up with data. I didn’t want to fall into that trap at RemotePass as I wanted our content to move revenue-related metrics
I began with a SERP and competitor audit to see what our audience was actually searching for and what others were missing. I looked for keywords with intent but low competition, and topics our ICP cared about but that no one had owned yet.
Those findings shaped everything that came next.
From there, I built a content gap list mapping high-potential topics, their search intent and how they tied back to the RemotePass product. For example, when I noticed HR ICPs were searching for help with choosing a global payroll solution, I added a few simple explainers about it to our roadmap. Those posts became some of our strongest performers later.
With the data in hand, I built a quarterly roadmap aligned with company OKRs. Every piece had a clear purpose: lead generation, brand awareness, or activation. That focus made it easy to report impact and get leadership buy-in.
To track progress, I set up GA4 and HubSpot dashboards. The tools were already there, but no one was using them to tell a story. I changed that. Each month, I shared short reports showing how content influenced pipeline and engagement. Once stakeholders could see the numbers, they started believing in the work.
✅ Pro tip:
Build a “Content Impact” dashboard with three KPIs that tie directly to business goals such as qualified leads, assisted pipeline, and engagement by ICP. Keep it simple and share it monthly. Once you do, people will stop seeing content as creative work and start seeing it as revenue work.
Pilot Content Experiments
Once you’ve nailed the strategy, the next step is to test it. Month two is where you start publishing, but every piece you release should teach you something.
At RemotePass, I focused on a few high-impact experiments instead of flooding channels with content. I published a thought leadership article on global payroll where I interviewed industry experts, including the CEO of Toggl. That piece drove and built credibility fast.
Next, I created a sales one-pager the team could use during demos. Then I worked on two case studies, Podeo and Logitech, showing how we helped real clients scale across borders. Those stories became sals and PR assets, proving what we’d been saying all along.

Each piece had a clear hypothesis behind it. The article tested authority. The one-pager tested clarity. The case studies tested social proof. After publishing, I watched performance closely to know which CTAs converted best, which visuals got clicks and which formats held attention. Those insights shaped what we did next.
Early experiments like these do more than bring quick wins. They teach you what the audience cares about, how internal teams use content and what actually drives business outcomes.
✅ Pro tip:
Create a few strong assets, track what happens, and use the data to refine your next move. The best content plans are built on small experiments that worked.
Review & Iterate
After you’ve shipped your first few pieces, slow down and review what happened. This part separates content managers from strategists.
At RemotePass, I made it a habit to share early results with leadership. For example, when the global payroll article went live, I showed how it led to demo signups from regions we hadn’t targeted before. That kind of context helped leadership see content as a growth driver and not a mere creative exercise.
I also took feedback seriously. I asked Sales how the new one-pagers performed in calls. I checked with Customer Success to see if case studies were being used. Those conversations helped me refine the roadmap and double down on what worked.
Some pieces needed rewrites, others needed better distribution. Instead of seeing that as failure, I saw it as calibration. Every iteration made our content sharper, faster, and more aligned with what the business needed.
✅ Pro tip:
Host a short “content review” session every month with Sales, Product, and Customer Success. Ask one question: Which piece of content helped you most this month? The answers will tell you exactly where to focus next.
Deliverables by the end of Month 2:
✅ 3 Strategic Content Pieces Published
✅ Quarterly Content Roadmap
✅ Performance Dashboard
✅ Collaboration Templates (briefs, feedback forms)
Month 3
By month three, you’ve built trust and delivered results. The next step is scaling what works.
At RemotePass, this was when I automated half my workflows, built templates for everything and made sure everyone from Sales to C-Suite could see the impact of our work at a glance.
Establish Repeatable Systems
By month three, you should be moving from doing the work to building systems that make the work run on its own. That’s how you scale without burning out.
After a few months at RemotePass, I noticed I was spending too much time recreating briefs, outlines and reporting templates. This practice wasn’t sustainable. So I started documenting every process that worked. I created templates for everything: content briefs, feedback forms, post-launch reviews and reporting sheets. Each one took a few hours to build but saved me weeks down the line.

Then I brought ChatGPT into the mix. I used it to automate repetitive tasks like drafting the first version of content briefs, summarizing competitor research and turning product briefs into marketing-ready plans.
Over time, this turned into a content engine. Writers and designers had clear starting points, and I had fewer bottlenecks to manage. Even reporting got easier because the templates handled most of the structure.
That shift freed up time for deeper, meaningful work such as messaging, storytelling and optimization.
✅ Pro tip:
Document every process the first time it works. Use AI to automate the boring parts, not the thinking parts. The faster you systemize, the easier it becomes to grow your output without losing quality.
Make What’s Working Work Even Harder
Once the system is running, the next step is to make it better. Optimization isn’t about doing more. It’s about getting more out of what already exists.
At RemotePass, I reviewed our content library by funnel stage (awareness, consideration and conversion). It helped me see where we were strong and where we were missing opportunities. Some blogs brought in a ton of traffic but didn’t move readers anywhere. Others like case studies quietly influenced deals but never got promoted.
So I started fixing the flow.
Awareness pieces got better internal links and clearer CTAs to push readers further down the funnel. Consideration assets got fresh data, updated screenshots, and stronger visuals. Conversion pieces like case studies got turned into smaller, shareable snippets for social and sales enablement.
I also repurposed top-performing articles into videos, carousels, and email sequences. One blog later became a short video that drove even more engagement. The goal was to stretch every strong idea until it gave us everything it could.
Each month, I tracked what worked and what didn’t. Then I adjusted. Over time, this rhythm of review, repurpose and refine made our library sharper, lighter and more effective.
✅ Pro tip:
Once a quarter, pull your top ten pieces by performance and ask, how else can we use this? Update it, repackage it, or distribute it again. The best-performing content is often the stuff you’ve already made.
Be Visible
By month three, your work should be speaking for itself. But that doesn’t mean you should stay quiet. If no one knows what content is doing, they’ll assume it’s doing nothing.
I started the habit of sharing good news at every chance I got. When a blog hit a milestone, when a campaign outperformed expectations, or when a case study helped close a deal, I shared it. Small wins compound when people see them often.
I also shared a monthly SEO report across the company so everyone could see how our work was performing. It kept the momentum alive and reminded people that content was moving real numbers.

Outside internal visibility, I also looked for ways to get the company and leadership in front of the right audiences. For example, I pitched Wesley, our previous Head of Sales, to platforms like HARO so he could share his take on industry topics. That single pitch got him quoted in a few publications and boosted both his and RemotePass’s credibility.
Those small visibility plays built long-term trust and showed leadership that marketing could create value beyond the blog.
✅ Pro tip:
Visibility compounds. Share wins, tag teammates, and spotlight leaders. The more people see impact tied to your work, the easier it becomes to get buy-in for the next big idea.
Set a Long-Term Strategy
Once things are stable, zoom out. Month three is when you stop thinking in weeks and start thinking in quarters.
I drafted a simple six-month roadmap with projected KPIs. I knew quarterly goals could shift and we’d probably adjust along the way but it gave the team direction. The roadmap outlined what we’d focus on, how success would be measured, and what resources we’d need to hit our targets.
I also started looking for new growth channels. At that point, we were doing well with blogs and SEO, but I wanted to diversify. I recommended building a newsletter, exploring community partnerships, and testing co-marketing with HR and fintech brands. Those small steps helped us expand reach without stretching the team too thin.
To keep everything grounded, I set up a quarterly content retro. It was a simple review session that compared what we planned against what actually happened. It helped us stay accountable and align with leadership’s OKRs, especially as priorities changed.
By the end of the third month, we had rhythm, visibility and a plan that could flex as the business evolved.
✅ Pro tip:
Plan in quarters, not chaos. A six-month roadmap gives you direction, but retros keep you honest. Review often, adapt fast, and make sure every idea ties back to a real business goal.
Deliverables by end of Month 3:
✅ 6-Month Content Strategy
✅ Documented SOPs
✅ Company-Wide Content Reporting Framework
✅ Thought Leadership Initiatives Launched
Final Thoughts
This 30/60/90-day plan was how I set myself up to win as a Content Marketing Manager at RemotePass. It helped me go from learning the ropes to leading launches, earning trust, and driving results that mattered.
If you’re stepping into a new role, don’t rush to prove yourself with quick outputs. Focus on understanding the business, building systems, and showing how content impacts revenue. Once people see that connection, you stop being the “blog person” and start being a growth partner.
If you’re growing a content team, this framework can be your starting point. And if you’d like help adapting it to your company’s goals, I’m just a message away.




This is real work and well done! I could read and walk through the process. Honestly, content marketing remains the foundation to sales and marketing. You've done well and I learnt a lot, too.
This is a really good read, thanks for sharing what worked for you. I definitely learnt from this!
This was really helpful. Thank you as always, Jeremiah.
This actually left me wowed. It started quite slow and I was wondering where it will lead and boom, it exploded right in front of me and I am here grasping at pens and notes.
However, in a case where you joined a team as an officer where you report to a manager who expects delivering from week 1, how do you get to manage this. I mean, it's hard to explain that you have a long term plan when your KPI is tied to the actual outputs. How would you advise to proceed?
Second question, in a situation where you are no longer new in the organization, how do you redirect things. I understand that it's never too late…
This is really Insightful! Thank you for Sharing.