Senior Content Strategist earning $120,000/year
Welcome to another post in the $100k Club series. You can see the full series here. This is….
I don’t know about you, but I don’t get many unsolicited job offers from CEOs.
The timing was terrible because I had just stepped off the plane from a warm-and-fuzzy company retreat with Butter—another seed-stage startup at which I was the Content Lead.
The message wasn’t completely out of the blue, though. I had been freelancing on the side for Alex and Dock for nine months, writing blogs through the Superpath Marketplace.
After a few more chats, we decided we were a fit for each other and I took the Content Lead role as Dock’s first marketing hire.
This is actually my third time in a row as the first marketing hire and solo marketer, so I’ve unintentionally carved out a niche for myself as a lone wolf.
In this post I’ll share a super-tactical breakdown of my first 90 days as Content Lead at Dock, then I’ll follow that up with some lessons and takeaways to help you avoid making some of the mistakes I made in my first few go-arounds.
Here’s a rough itinerary I followed in my first 12 weeks at Dock. If you’re in a new Content Lead role yourself, you can use my pace as a benchmark.
Of course, most of these projects are still ongoing months after I started them, so think of these more as starting dates for each project rather than completion milestones.
I had two goals for my first week:
Here’s how I did that.
Onboarding chats: I had a head start on a typical new hire because I had already been freelancing for months, but Alex and I spent one hour a day meeting until we felt we didn’t need to meet daily anymore (about two weeks).
Our chats were one-third onboarding, one-third throwing out marketing ideas, and one-third personal stuff—like chatting about our dogs, familiars, or TV shows we were watching. That stuff matters too.
Expectation setting: As part of my onboarding process, we were very intentional about setting the table for what our working relationship will look like. That included writing down how we’ll work together, how we'll measure content success, what I would be responsible for, tools we’ll use, what our budget will be, and what our short- and long-term goals are for the role.
Most of this was already discussed in the interview process, but it’s good to overcommunicate on these things off the top.
Getting to know the business: I immersed myself in the product and business as much as possible. I listened to sales call recordings, read previous investor and product update emails, made my own Dock workspaces, looked at our product roadmap, and absorbed as much as I could about our growth strategy.
Tools setup: As a one-person content team, I live in and own the tools, so I spent the rest of my first week setting up an Airtable as our internal CMS.
My primary goal was to create an inventory of our existing content. I created a database with interconnected tabs for:
As I did that, I also worked on creating systems that would help me scale myself long-term, like a workflow to import keyword data from Ahrefs, an automation to create Google Docs briefs directly from Airtable, and an automation to push published content to Slack.
By the time I had set this all up, I had a great idea of the lowest-hanging fruit for content, and I was ready to roll.
Once I had a central record of all our content, it was super quick to go through our website and blogs page-by-page to make small copy improvements and find quick SEO wins.
I also went through the existing blogs on the site and cleaned up any inconsistencies, glaring design errors, or missing internal links.
Doing this gave me a great sense of where our website could use quick design upgrades to improve readability and navigation, so I created some Figma mockups for our designer/co-founder, Luc.
For example, I asked for a new Webflow page template for our product template pages or minor blog design improvements that would make my life easier.
I also took time to answer Help a B2B Writer requests daily to land links on high-authority websites and grow our domain authority (I still do this almost daily).
As I worked through the clean-up work, I started documenting our strategy in Notion.
Most of our strategy was already agreed upon in our interview process (part of my hiring assignment was to put a content strategy together), so it was mostly an exercise of getting our ideas on paper.
Jimmy did a nice write-up on Dock’s content strategy here.
In summary, we decided to:
While documenting our strategy, I took most of my inspiration from Jimmy and Ryan Law’s How to Create or Refine a Content Marketing Strategy blog post. Superpath’s template was helpful too.
The most challenging part was setting measurable goals for our content program. We decided to approach it from two angles:
To start, we set big, hairy, North-Star goals:
To give ourselves measurable goals short term, we decided to focus on publishing cadence instead of output metrics like rankings, traffic, or leads.
Here’s a rough content publishing cadence that I’ve been mostly successful at following:
Because our goal is to post eight blogs per month, I needed an efficient process for working with freelancers.
We loved the four articles we were getting monthly from Superpath, but we wanted to experiment with finding our own freelancers too—doesn’t hurt to diversify.
I didn’t want to spend a lot of time searching for writers with subject-matter expertise, so I looked for writers with consistent bylines on other B2B sales websites we respected and paid them their rates. We’ll worry about optimizing the cost later.
My biggest concern was bringing freelancers up to speed on product knowledge, as we employ a product-led content strategy.
So I made an onboarding workspace in Dock that introduces our writers to:
I then worked out a content production workflow in Airtable and Google Docs for creating briefs, assigning them to writers, editing first drafts, sending them back to writers for edits, doing a final edit myself, then publishing to Webflow.
By week five, our Account Executive, Andy, flagged the need for some case studies or social proof, as prospects kept asking for them.
I built out a case study strategy and template in Notion. The Case Study Buddy blog was a goldmine of inspiration.
We decided we wanted:
Our CEO built a spreadsheet of our strongest case study candidates.
My biggest concern was folks saying no, or the process taking a long time, so I made a case study onboarding Dock for the first two interviewees to make the process smoother.
Alex had already made dozens of keyword-targeted templates, so I got to work on making landing pages for them.
I had already asked for the landing pages to be re-designed back in week two, so now all I had to do was enlist the help of a freelancer to start writing content for all the pages.
As we do for blog posts, I provide our freelancer with a brief, target keywords, and a Clearscope link for every page. They’re still doing about five pages per month.
By week seven, I was mostly in the weeds. But in the in-between times, I started putting our social media strategy together.
We decided to go all-in on LinkedIn as that’s where our sales, marketing, and customer success audiences live. We opted to be fairly lean about it at first by repurposing content sections from our blogs into mid-length LinkedIn posts.
I use a combination of Airtable and Publer to schedule our posts. We chose Publer because it lets you pre-schedule LinkedIn comments.
By two months in, the wheels were all in motion and there was no way out.
The first freelance blogs were coming in, new template content was going up, I was writing a million briefs a week, the case studies were progressing…
I finally felt like I was “in” the job.
In week ten I presented our working marketing strategy at our company all-hands (we only have eight employees by the way).
We didn’t want marketing to be known as the function that “posts memes”, so I explained our content strategy and how all the channels would work together:
I also explained why we were prioritizing long-term organic traffic and gave some examples of stuff I had already made.
To throw another log on the fire, Alex wrote a bunch of thought leadership pieces for third-party sites that I’d have to edit, such as this article for Sales Hacker.
Editing these gave me a much stronger understanding of the space we were working in.
On top of the now overwhelming mountain of work I had made for myself, we were one month away from launching three new products.
That meant overhauling our home page (which was a joint effort between me, our CEO, and our designer), writing launch blogs for every product, making demo videos, and scheduling email campaigns and social posts.
Since then, we’ve launched all our new products, fired up our social campaigns, and done an okay-ish job at keeping the freelance engine running.
I’ve been doing my best to establish what “normal” feels like to figure out how much capacity I have to take on new projects—like a new podcast we’re planning or more ambitious SEO projects.
My goal is also to spin up some sort of monthly report soon.
Reflecting on how my first 90 days went at Dock—especially compared to the first 90 days at my past couple roles—here are some lessons that might help you in a new role.
Most content folks come from an inbound/SEO background and therefore default to making top-of-funnel/acquisition-focused content.
But at a product-led growth startup, for example, where your product is your biggest acquisition driver, your primary focus might need to be more on activation content (e.g. product guides).
If you sell to enterprise companies, content’s primary role may supporting the sales process, or helping with employer branding.
So rather than jumping in with an SEO plan from day one (like I did in my first few content lead roles), spend time getting to know the business model first.
Most of your job is collaborating with your manager. The smaller your team, the more you’re going to lean on them for resources and buy-in.
The only time to dictate how the relationship will work out is the beginning. It’s when you’ll get the most face time. And it’s harder to break communication patterns later.
So work with your boss from the get-go to determine:
For example, here’s what Alex shared with me about his communication style in my onboarding documentation:
As a team of one (or as a small team), you have to be a Swiss-Army knife, but you can’t do everything alone.
For example, if I need a quick graphic for a blog, I’ll try making it myself. But once I’m spending too much time on it, I’ll rope in a designer.
My point: you’re going to need help. Use your early days to make your presence felt and build a content culture within your organization.
In my first few weeks, I:
This broke the ice and established our content strategy as a collaborative effort. Plus it helped me avoid being thought of as the department that only makes memes.
By far the hardest part of being in a senior marketing role at a new company is being an outsider to your niche. Unless you’re joining a company that markets to marketers, it’s likely you won’t be a subject matter expert.
Immerse yourself in your niche from day one—and figure out how you’ll stay informed.
At Dock, our ICP is Revenue leaders. In our content, we talk about how Sales, Customer Success, Marketing, and RevOps can collaborate to generate more revenue as a team.
But I only knew about that from a marketing perspective.
I waited a little too long to follow our competitors, and realized much of what I had written in our content wasn’t as original as I thought it was.
Marketers love a well-documented plan—myself included.
But things will change constantly at a startup. Your product will change weekly. Your target customer will change quarterly. Your messaging will change almost daily.
If you over-plan, over-document, and over-process, you’ll never get anything done—especially if you’re a one-person team.
Until your content program starts to mature, work in shorter, two-week cycles and build the plane as you’re flying it.
Instead of committing to channels or tactics, commit to your content philosophies. For example, our content principles are:
On that note, you can’t do it all as a one-person team. Don’t compare yourself to huge content teams with big budgets.
Instead, focus on one channel at a time. Figure out how to do that channel really well and then optimize it before adding another channel.
For example, I’ve focused almost entirely on our blog process to start. I’m close to the point that I can hand it off entirely to freelancers and spin up a new channel.
If I tried to launch lots of channels at once, my plate would be completely full of busy work.
On my first day, Alex told me, “The worst hires end up in Strategy Land for way too long.”
So I focused on getting some stuff published within my first few days. For example, once I had five blog topics lined up that I knew we needed, I stopped brainstorming and moved on to recruiting freelancers.
I could have planned out a 3-month calendar, but that would only delay getting some early work done.
You live in your tools as a content lead. So build out your tech stack as early as possible and automate as much as possible.
That said, don’t waste too much time building perfect automated workflows that might not stand the test of time.
For example, I spent a while making an Airtable automation that would ping us on Slack every two weeks to rate all of our latest content ideas. Turns out that was overkill and we didn’t need it.
Instead, don’t automate something or come up with a process until you’ve done it at least 3-5 times manually first.
It’s a running joke that every marketing leader redesigns the company website on their first day.
At Dock, our design was great, but I wanted to re-write all our messaging and re-organize all our pages, but I stopped myself.
Even if it’s terrible, leave your website as is for a few months (minus some minor upgrades).
Our website clearly communicates what we do and shows off the product, so it does the job for now. We don’t have millions of visitors, so tiny tweaks won’t matter.
I’ll wrap this up with empathy for other content leads or solo marketers. This is a really hard job. Every lead I talk to has completely different pain points or anxieties about their work.
There’s no playbook for being a solo or small content team spinning something up from scratch. So much will be dictated by your product, budget, team structure, etc.
Treat your role like it’s a really difficult puzzle to solve, and you don’t have the picture on the box.
Just start with the easy pieces along the edges. Then work on the most stand-out pieces in the middle. Eventually, you’ll get to the point where you’re just working through different shades of blue in the sky.
Suddenly you’ll look at the big picture and realize you’ve come really far, even if it felt confusing along the way.
Someone put that in a fortune cookie.
Feel free to follow me on LinkedIn where I’m continuing to share my journey of building Dock up.