Hiring and growing your team is one of the toughest things you have to do as a small business owner. The reality is many people on your team are going to have to wear multiple hats, and it can be expensive to hire specialists for everything. Chances are you don’t have tens of thousands or hundreds of thousands of dollars each month to spend on payroll — so every hire really matters. It is an expensive decision which is why today, I want to talk about the types of hires to consider for your business.
If you hire the wrong person and you spend time and money training them, the stakes feel extremely high. And can I just be honest? It’s just uncomfortable when situations don’t work out. We want to get it right, and there’s a ton of pressure around making a hire in your business, whether that’s an employee, a contractor, or any type of investment. So let’s get into it.
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What Sparked This Episode
Over Christmas, someone reached out to me with a seemingly huge Pinterest account. I did my research, and while front-facing Pinterest analytics can be incredibly misleading, I saw that she had 2.5 million monthly impressions and over 100,000 Instagram followers. I thought this was more of a volume-based business — not a service provider — but I was excited about the idea and felt I could really help her.
We went back and forth a few times. I think one thing that affected our interaction was that she reached out around Boxing Day, and I didn’t have childcare. I’m not making excuses — it’s just a reality. I was probably taking about two business days to respond each time, which could have contributed to her going in another direction.
But what I actually want to talk about is why she told me she went in another direction: she wanted someone who could handle Instagram, social media, newsletters, and Pinterest. “It’s just easier to go with one person,” she said.
The Generalist vs. Specialist Question
In a way, I agree — of course it’s easier to go with one person. But part of me thought, is there really someone who can do all of these really well? Especially at the level she was operating, where you really need to go for volume with an established account. It actually felt a little more risky to me.
This wasn’t a small startup. Based on what I could see from the outside, she’d been in business at least a decade — many pages on her website, a huge Pinterest account. At that stage of business, I’m not sure going with a generalist across all these platforms is the right move, because the way you run an Instagram account is so fundamentally different from the way you run a Pinterest account.
I don’t think you can specialize in both. Unless you’re going with an agency — and agencies will have the price point to support how different those platforms really are, because they truly are two different specialties. I would never claim to be an Instagram expert. Never.
When a Generalist Actually Makes Sense
That said, this is not going to be a “never hire a generalist” episode. Quite the opposite. As a small business, it often makes more sense to go with a generalist because it is extremely expensive to hire experts at everything.
I want to talk about the four most common hires I’m seeing for online business owners, because sometimes we just hire whoever is immediately in front of us — or whoever solves the problem we’re currently having at this exact second — rather than thinking strategically about what we actually need.
Sometimes we see an Instagram post from someone speaking directly to our pain point and immediately feel like we need to hire them. So let me walk through the four most common types of hires I see for online business owners, so you can think more strategically about what you actually need.
4 Types of Hires To Consider For Your Business
Hire #1: The Virtual Assistant
A virtual assistant — or some kind of assistant — is generally going to handle task execution and admin work. They’re typically not responsible for strategy. Think inbox management, scheduling, uploading your podcast and blog content, formatting emails or newsletters, customer support, making Canva graphics, updating your website, data entry. There are even virtual assistants who specialize in tech, so if you hate the tech side of your business, that might be someone worth looking into.
A VA is a great first hire, especially if you haven’t outsourced anything yet — because most of the time, you are drowning in repetitive tasks and spending way too much time on admin. You just need less expensive operational support.
This is not the show where I’m going to tell you to go on Upwork and pay someone $5 an hour. I would never. But a VA role is generally going to be less expensive than what I’m about to talk about next.
One thing I really want to stress: the expectation of skill level has to match the compensation. If you’re hiring a VA but expecting them to grow your Instagram, edit your podcast, manage your inbox, and basically run your content strategy for $20 an hour, five hours a week — that’s just not realistic. If someone is coming in with no existing skills, a lower rate makes sense because you’re also training them. But if they’re coming ready to work out of the box, expect to pay more.
The key thing to understand about a VA: they execute tasks you already know need to be done. They’re typically not deciding what tasks matter, helping you prioritize, or weighing in on strategy. You tell them what to do, and they do it.
Hire #2: The OBM (Online Business Manager)
An OBM is a huge gray area in the online space, and I want to clear some of that up.
An online business manager is responsible for running the backend operations of your business. That includes managing team members, overseeing launches, project management, improving systems and workflows, holding the team accountable to deadlines, and translating strategy into action steps. They take your big ideas and create the plan to execute them — then hand that plan to a VA, or come back to you with recommendations like, “We should probably incorporate this software.”
OBMs and virtual assistants are not the same thing, but they get confused a lot in the online space.
Here’s my honest opinion: you don’t need an OBM if you don’t have anything for them to manage. Having an OBM as your very first and only hire doesn’t really make sense on an ongoing basis. That said, bringing in someone for systems support as a team of one? Big fan of that.
To be clear: an OBM is best for businesses that already have team members. They need that extra layer between the owner and the team. An OBM can sometimes be an executor too, but typically they’re not — meaning they might handle small admin tasks, but they’re not the one checking your inbox or creating Instagram content. They’re managing the people, projects, and systems that are doing that for you.
Hire #3: One-Off Marketing Support
Marketing support can fall into a few different categories. You can hire a general marketer, though there will be some overlap with a VA in that role. The honest truth is: unless you’re hiring a full marketing agency, you’re going to have to be heavily involved in the strategy yourself. There’s just no way around it.
Hiring a marketing agency is always an option — they have experts across every platform and it’s genuinely hands-off — but you are paying for that level of support. We’re talking thousands of dollars a month. I talk to a lot of small business owners, and I don’t know many who have hired a marketing agency and been able to sustain the investment long-term. Usually it’s, “I paid $5,000 a month for six months and then I was done.” Even people making decent money often can’t maintain that. In my opinion, marketing agencies are really more suited for corporations.
So let’s talk about who to actually hire for marketing, and whether I think it’s worth it.
Website SEO
First up: an SEO specialist for your general website SEO — and I’m not talking about myself here, I’m talking about the foundational stuff. This is an investment I believe everyone should make, whether you’re putting in the time to learn it yourself on YouTube or hiring a professional to take it over.
Basic website SEO is genuinely set-it-and-forget-it. Not that you’ll never touch your website again or rank on page one forever no matter what — but it really is the gift that keeps giving. It makes your blogging more effective, drives more traffic to your site overall, and helps everything else work better.
Branding and Website Design
I’m going to loop branding and website design in here too, because these are investments you’ll likely make once and then be good for a few years. They’re the foundation of everything else you do in marketing, and they’re worth getting right.
One thing I’ll say: I don’t think it’s worth hiring the cheap option here. I’m not saying you need to spend $10,000. But if you feel like you’re settling — whether it’s because someone agreed to a service swap, or they’re the only one in your budget, or they’re brand new and you’re essentially their first client — I’d pause.
And here’s why, because it’s actually less about their raw talent and more about this: branding and website design is an emotional experience. You are watching someone take your business and create something visual with it. Every person I’ve talked to who has gone through the process says some version of, “I had no idea I would feel this way about it.”
We see it online like it’s all fun — new logo reveal, pretty mockups — but there is so much more that goes into proper branding and websites than it looks like from the outside. It will take more of your time than you expect. You will be more invested in it than you think possible. It can be genuinely stressful because you’re putting real money into something and you want to love it. And in my experience, you will not have full confidence in the result unless you hire the person you actually want.
Funnels
You could also hire someone to set up a funnel for you, but I’d only recommend this if you’ve already done it yourself first. I know that’s an unpopular opinion, but I think setting up a funnel and writing the emails is something you have to do yourself at least once so you understand all the moving pieces and can test whether your offer actually converts. It’s also a more expensive hire, so you really should only be ready for it once you know your offer works.
Hire #4: Ongoing Marketing Hires
Now let’s talk about the ongoing marketing people you could bring on.
Content Marketing / Blogging
Obviously I’m a fan of content marketing — you could hire me to handle blogging, Pinterest marketing, podcast-to-blog repurposing, podcast scripts, YouTube scripts, anything search-driven.
What I want to highlight specifically about blogging: I take it almost entirely off your plate. Most clients love that I come in with a plan, follow it, take their input, make adjustments — but they stay pretty hands-off. That’s what makes blogging a great option if you want to grow your marketing without having to do a ton of the work yourself.
The flip side is that you do need to be prepared to invest for a sustained period of time — six to twelve months is what I tell people. Budget-wise, blogging runs around $500 a month as a starting point.
Social Media Manager
A good social media manager in 2026 is running about $1,500 to $2,500 a month. And the most important thing I want you to know before you hire one: you are not hands-off, babe.
If you’re the face of your brand, a social media manager is going to tell you what Reels to film. They’re going to want a lot of input on your content. And you’re actually going to spend more time reviewing and editing that content because your friends, family, and past clients are all on there watching — it feels very personal in a way that, say, a blog post never does. A blog post is seen by people searching on Google. Social media is seen by everyone who knows you.
That’s what makes social media so hard to outsource. I know so many people counting down the days until they can hand it off and never think about it again — and in my experience, that version of outsourcing doesn’t really exist. You are still very much involved.
Also worth doing the math: at $1,500 to $2,500 a month, how many services do you need to book, or products do you need to sell, for that investment to pay off? My personal opinion is that social media rarely delivers the strongest ROI compared to other marketing channels — but I know that’s not everyone’s experience, so I’ll leave it there.
Ads Manager
The last marketing hire I think genuinely requires a specialist: ads. A good ads manager is running about the same price point — $1,500 to $2,500 a month. And that’s not including ad spend. If you want someone good, you’re spending money — could even go up to $3,500 a month for the right person.
So, Should You Hire a Generalist or a Specialist?
Let me recap the specialists I’ve covered: blogging, Pinterest (same idea, different platform — around $500 to $1,000 a month depending on who you hire), social media/Instagram/TikTok, and ads.
Can you find one person who will do all the platforms and all the things? Yes. Can they possibly be an expert at all of it? No.
What I typically see is social media managers saying, “Sure, I can also blog for you, I can do your Pinterest too.” And what they usually do is repurpose content and lean heavily on AI — no judgment — but are they doing the SEO properly? In most cases, I don’t think so. Anyone can produce something that looks like a blog post. These platforms change constantly. I was just watching a training on what to do when a client is getting stolen pins that are hurting their reach — there are so many nuances now. When you’re investing your money, most of the time you want an expert.
To the person who sparked this whole episode — the one who said she just wanted one person to write her emails, manage her Instagram, and handle her Pinterest — I genuinely wish her the best. And I know I probably wasn’t presenting as the right fit, partly because I was slower to respond than usual over Christmas break. But in general, if you want excellent results from multiple platforms, I think going with one catchall person is a mistake.
Don’t Outsource Before You’re Ready
I also want to say this: I don’t think you should outsource your marketing — or anything, really — until your business model is solid.
If you’re not sure you’ll still be doing family photography a year from now, or if you’re still playing around with your offers and services, wait. In the first couple of years, there is just so much learning that has to happen first.
I’m currently reading a book called Designing Your Life — only about 10% in, but one thing the author said early on really unlocked something for me. He talks about how we tend to think we should sit down with a blank page and design the perfect life from scratch — but that’s not actually how things get designed. Think about product development, like the iPhone. They just solved one problem at a time and saw what happened.
That hit me, because I’m an Enneagram 3 and I genuinely cannot stop trying to optimize everything for even one second. But it reminded me: just fix one problem at a time. Specifically, the problem that is most pressing — or the one that’s going to get you closest to the life you actually want.
So if you’ve been pouring your time into Instagram and you are exhausted, and you want to outsource your blogging and build a platform you don’t have to think about as much? I love that for you. And obviously, I do that, hire me. (Sorry, that was cheesy — I’m recording this at night.)
LINKS MENTIONED
- Hire us to write SEO-driven blog posts for you
- Learn more about our Pinterest management services
- Learn more about working with our marketing agency here
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