Okay. I am looking for a support group! I onboarded at a very small startup about a month and a half ago and I'm building their whole content program from scratch. They had 5 blog posts with no strategy before I arrived and they wanted a very ambitious content strategy. I've spent the last month creating a strategy, getting the ball rolling on a few exciting and big content projects, helping with a complete rebrand and a 100% website refresh, hiring freelancers to help with a very ambitious video and social media strategy, and creating system after system after system to help with scaling. It's fun. It's exciting. There is budget for help wherever I need it. But everything is such a big lift right now and I can't delegate until I define what I need and have an example to point to for things we're outsourcing because we're still defining our voice. We have no marketing ops support -- which is our next to do. It's just two full-time folks. Me and the VP of marketing. And everything I do takes five times longer right now because we realize that things aren't working with X or Y (published a blog post by our engineers only to find out that our CMS doesn't have functionality for code snippets -- we're getting a new one next week thankfully but trying to solve for that took two hours alone one day!). Someone who has been here... please tell me it gets easier! Lol. I just want to get our program in place and running smoothly and have content ready a week or two before and not to encounter unexpected bugs. lol. I am finally outsourcing my first content program next week -- our employee spotlights (which we're doing a lot of because we have 30 open positions -- we are a 43 person company so it's a huge growth period) are going to be done by our admin person. I cannot wait to get more off my plate!

woof! I feel it—I was in a very similar situation years ago with a (then) small startup with just two people on content. It felt like we had to tear down everything (legacy systems, sub-optimal tools, a very messed up CMS setup) just to be able to actually start doing what we wanted... I don't know if this is going to help or make things worse, but: I don't know if it gets 'easier' overall, it just potentially gets more complex in slightly different places 🙂 I think you have the right approach, though: build a strong foundation, then start delegating the 'doing' wherever you can. It took us 6-9 months to start operating like a well-oiled machine... and then we got to have a lot of fun!

Seconding what @stocky-zebra-68352 said here! As someone who's built her career in early-stage start up, it can be a lot of kinks that need ironed out. The most important thing is to be realistic about what you can accomplish with the resources you have. It's great that you have budget to externalize things – that helps so much. It does get easier. Sometimes you'll need to do what Fio said and tear things down that don't work, and replace them with the things that do work. I used to have to upload blog articles in the most messed up CMS at a former company, and I'd have to save changes twice periodically because it liked to crash in the middle of uploading a piece. It didn't even have HTML so I couldn't brute force it. It took some time to convince them, but getting a new CMS and a few key automation tools helped so much.

It gets less tactical and execution-oriented if you scale a team. It gets messier and harder to juggle more things and more people. You have to keep more plates spinning and there are more trade-offs and more demands, often conflicting. Strategy gets more complex and demanding. You’ll compete at higher levels, against better people, better companies. And if you’re succeeding, more competitors will keep joining the fray. Who’d pay us more if it got easier? That would be illogical for any business. It also would make us more dispensable. If it gets to a point where work is easy at a startup, it’s not growing enough and/or content probably isn’t a high-value function. That’s risky as a business and as a content person in the company.

First of all, I’m managing a full rebrand right now, and I just want to say, I feel your pain — exhausting and fiddly process, and it’s somehow turned up a billion inadequacies in our CMS that I did not have any reason to notice before LOL I went through all the rest of this in my current role, too! Although my situation was easier, because the content program I set up was less ambitious: I chose to focus on SEO and treat all other channels as ancillary — basically more ways to distribute our search-informed long-form content. But it was still intense. The transition has pretty much been what Maggie describes. At first, I was the person who downloaded Postman to troubleshoot APIs, did my own blog design on Figma, wrote every sentence, created Instagram grid graphics, and so on. Now, much more of my time goes toward team (and contractor) management, which I — as a consequence of my temperament and personality type — find more challenging haha, though also really rewarding. I really miss the nitpicky purity of all the execution work, but there’s no denying that I work less now. I’ve been able to cut down my weekly working hours by 10% from my one-woman-show days

Thank you all! I likely was a bit imprecise at the 'getting easier' part. I just don't want to spend my days fighting with a horrible CMS lol or -- as happened today -- having to get an entire demo reshot because the dev didn't look into the camera while recording. Truly lovely colleague but I am now adding 'Look into the camera' to my demo recording checklist. And we're adding a step where the devs send me a test clip before they record the whole thing to problem solve in flight. I love the ambition of our content program and we'll be outsourcing a lot more starting in December/January which will help. But yes, I'm currently doing an ambitious video heavy social strategy (3-5 videos a week) that needs very high production values (I had to hire a freelance Unity developer, a professional editor, and am working with a conversation designer just for that alone), an SEO blog program, a thought leadership program, an employer branding program, an engaging mini site that I'll work with a web development firm on, influencer marketing, a large research project and report, sales enablement materials because we have none, and about three other things I can't talk about lol? Outsourcing content marketing ops is the next step then I'll likely work on outsourcing the SEO content writing. We'll be passing off the influencer marketing to our PR agency soon. We're hiring a community manager who will help with content distribution. Eventually, the video creation process will be easier -- I now have my team for that in place, at least. And it will absolutely get bigger but we are also hiring a full-time creative producer to help with some of the marketing materials and client work and we're going to have a main PR firm AND a second PR firm just to help with execution on the more ambitious content projects. So, help is on the way! But it won't all be running smoother until mid-November or December. Lol.

I feel your pain. I think easier isn't necessarily the right word- but in context, manageable is a better fit. Sending you all the content good vibes!

You might mean how soon will you feel a sense of control. Correct me if wrong, please. At early stages, it’s typical to be pushing uphill if you’re joining an early stage startup. If anything’s been built at all, it will usually be crap, or you might have nothing at all and have to build things from scratch. And meanwhile you have little or no leverage. It also depends on what you’re trying to build. If you’re outsourcing a lot, it will go much quicker than if you’re building a team, especially a large one. Any experience in early stage is valuable, because you’ll know how to do it better and faster in the future. Also, you’ll be better equipped to guide others. When I was building my team a NerdWallet, I built everything from scratch, because I ran content autonomously — the VP of marketing and I were peers and we both served on the company’s exec team. I did all of my own hiring and didn’t outsource anything, so I thought about building in stages. At early stage, startups don’t necessarily have enough draw for the best talent, so I didn’t want to hire managers, because I knew that their ceiling would limit who’d be willing to report to them. So I hired about 20 people before we were able to produce enough quality and show enough momentum and investment to start drawing the caliber of managers I wanted. That took 14 months. Till then, I managed everyone. It was as hard as shit, but holding out was one of the best things I did early on — it later helped give us much stronger leverage. Boiled down: Say you hire a C+ or B- manager. No A level writer or other IC will want to work for them for long. You’ve capped yourself. The stronger managers you hire, the better the quality of ICs you can draw and the longer they’ll stick. Those are competitive advantages. How I realized this: I was a high-performing IC for many years, with zero interest in managing. I had my pick of jobs, so why would I ever agree to work for a shitty manager? The best ICs always have choices. At early stage, the only reason I joined NerdWallet was I was able to negotiate a big enough role, with enough scope and equity to make it worth my while. But that’s not something we could offer all hires. That’s important to remember for hires: Always consider why they’d join and why they’d stick. Everyone isn’t incentivized by the same things.

Yes! A sense of control is a better descriptor. While there will always be a degree of chaos in any job, I was in my last role for 8 years so I became quite good at anticipating the chaos involved. I want to better predict when I need to plan extra time for things or what road bumps I'll encounter. I'm very systems based and process-oriented and a lot of that is to anticipate and cut down on the chaos. It eventually works pretty well -- but there is always a learning curve. We're currently focused on bringing on agencies and contractors to support content -- which has actually taken up considerable time finding the right people. I currently 'manage' four contractors and I love the way you think through how to ensure folks have an experience that helps them grow their careers. That's really important to me. We won't be hiring full-time in content this year... but we will be hiring 1-2 roles that will take over some parts of the content program: a Community Manager and possibly a Dev Rel person. This year will be about building the capabilities of the content program and showing the business benefits of content -- which will be significant since we are in the entertainment/gaming/experience space. And then, we will need to decide the best scaling strategy. But we're in a bit of a zeitgeisty space so that could change if things quickly explode. Next week, my boss will be in town (we work remotely) and we'll be strategizing the next year or so -- which will be good. Thank you all for your thoughts! Much appreciated and helpful.