Investing in Your Marketing: Insights from an Outsourced Marketing Director
Many of my blog posts lately have played with ideas of what many people know and believe virtual assistants and online business managers to be. I see so many small business owners try to use a VA or an OBM for all things in their business without having any actual strategy or having consulted someone whose specialty is in the area they are needing help with. These range from bookkeeping (needs a bookkeeper), to branding (needs a brand strategist), to financial operations (needs a financial ops manager), and even marketing (needs a marketing director).
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First of all, please know that I’m not judging anyone who does this. We’ve all done it at some time or another. Running a small business is hard, especially when running a micro business. Funds are tight; we are not Amazon or Meta. We have to perfectly balance every dollar in our budget and we have to be careful who we trust.
Which is exactly why I want to help my clients and the people who find me understand why hiring the right person for each job is the best move they can make for their business instead of taking on jobs where my team and I are not the right fit, which we know is not what’s best for your business.
In this blog post, I share what I learned through a collaboration with Madeline Willett of Aligned Marketing when we interviewed each other about our roles as service providers to small businesses and how investing in your marketing strategy via a marketing director or strategist, even if you’re still in the early stages of your business, is incredibly beneficial to your business journey.
Who is Madeline Willett?
Madeline Willett is a marketing strategist and outsourced Marketing Director for small- and medium-sized businesses that are ready to scale. Basically, she helps businesses like yours (and mine) who don’t have large marketing budgets or in-house marketing leadership get the director-level marketing strategy they need without having to hire someone full-time or pay that full-time price tag.
When you’re running something small like we are, a full-time marketing director doesn’t make sense. Madeline’s marketing services are there when we need them and we are able to pause when we need to, which is a huge relief when you need marketing direction for your business.
Basically, Madeline:
Helps with marketing only when you need it.
Builds marketing strategies and plans and then implements them with her team.
As your outsourced Marketing Director, Madeline brings all the leadership, clarity, and execution you need to your marketing without needing to build an entire department by yourself.
Do Small Businesses Really Need to Invest in Their Marketing?
During our conversation, Madeline and I both noted that we often see marketing be pushed to the bottom of every business owner’s priority list. We get it; marketing feels expensive, uncertain, confusing, and like something only “big businesses” can afford.
But “marketing is literally how you get your message into the hands of your customers” (Madeline). If you don’t do some form of marketing, no one will know about your business. If no one knows about your business, you won’t have customers. If you don’t have customers, you don’t have a business. If you really think about it, that kinda makes it one of the most important things in your business.
The Answer? Absolutely!
I’ll agree, if you’re a new business owner, a Marketing Director is not what you need right now and probably feels WAY out of reach. That doesn’t mean you shouldn’t or aren’t investing in your marketing in some way or form.
As Madeline shared with me, “every business needs marketing, whether you’re small, scaling, thriving, or struggling.”
So Why Do We Hesitate?
Marketing has an element of unknown. It’s difficult to tell if someone will be able to capture your voice, your style, or your preferences. Plus, we typically see it as extremely costly and out of budget for us.
I think what really holds us back from investing in marketing is not feeling like what we have or know is enough–especially when putting a price tag with it.
But you don’t have to have all the answers before you hire someone to help you with marketing. According to Madeline, not knowing is exactly why you need marketing support early on in your business, whether that support be with a marketing director or with someone else. The important part is developing a strategy.
Understanding Your Unease with Marketing
Clearly we all have a ton of uneasiness with marketing. There is so much we cannot answer and nothing is certain. We’ve all had the “What if I spend all this money and see no return?” thoughts.
As Madeline says, “Marketing is a process of experimentation. You define a strategy, carry it out, and then evaluate what worked and what didn't. You experiment, optimize, and eventually land on marketing that serves you well, delivers ROI, attracts the right customers, and creates a clear customer journey. But none of that happens if you ignore it or wait until you're desperate.”
So what do we do if we’re stuck in our head about taking the next step?
Relieving Your Financial Fears
You and I both know you are not going to go out after you read this blog post and invest $100,000 in marketing–because you’re a small business with a small budget.
Here’s what can do:
Review your budget. Determine what you can allocate toward marketing.
Research marketing strategists or directors based on what you know you can spend on marketing.
Meet with potential marketing experts that you think you will get along with.
It’s possible to get marketing help on a budget (even from a marketing director like Madeline!) and if you look at it from the perspective that marketing is likely the most important thing in your business, you may be able to adjust your budget to make more room for marketing in your budget. If you’d like to talk to a bookkeeper about your budget and get help deciding how much you can budget for marketing, I recommend Annelise Velazquez at Yellow Sky Business Services. You can learn more about her services here.
Facing Your Negative Mindset Around Marketing
I asked Madeline what she wanted small business owners like us to understand about marketing. She said, “understanding that results won't be immediate and that what your competitors are doing (or spending) doesn't necessarily translate to what will work for you. I [Madeline] can run the same marketing strategy for two different competitors and have it perform completely differently. That's because there are different brand elements, audience nuances, leadership styles, and sales processes at play. Marketing isn't one-size-fits-all.”
I know for me and the majority of clients I’ve worked with, that’s where the biggest fear lies. We struggle with making decisions in our business around things that are not a safe choice. We don’t like to take risks, especially if they cost us money.
Here’s the thing, waiting until it's already too late—when you're desperate for customers and have no budget left—is obviously not the time to start experimenting. We have to learn to do what we can when we can so we don’t end up in these situations and we have a marketing strategy that works for us, our business, and attracts our clients.
Feel Comfortable Outsourcing Your Marketing With Someone Who’s Done the Outsourcing
Madeline’s business is called Aligned Marketing. I asked her how she helps businesses align their marketing with their values and priorities and why doing so was so important to her. I loved her answer to this question so much, I’m not even going to spend time editing here, I’m just going to share what she said, word-for-word.
Madeline Understands You Need a Marketing Director or Strategist Who Gets You and Your Goals
Here’s what Madeline had to say:
“Part of why I started Aligned Marketing is because I saw a real challenge when I was working as a Marketing Director inside small businesses. I'd watch myself and others either struggle to implement everything ourselves or we'd hire a bunch of different agencies - but we'd lose transparency, context, and alignment in the process.
Those agencies were managing tons of clients. They weren't involved in our day-to-day. They didn't always understand our goals clearly - and it wasn’t their fault! And we'd spend so much time explaining context, chasing updates, or trying to figure out if what they were doing even tied back to our bigger picture.
So I saw this gap where I could step in and help businesses that needed director-level leadership, someone who could actually bring together the teams, the knowledge, and the strategy so everything was aligned. Not just "aligned" in a fluffy way, but aligned in a way that meant we weren't accidentally spending money in areas where we didn't understand the ROI, and we weren't constantly re-explaining our mission to people who should already get it.
This is especially important for mission-driven organizations. You want your values, priorities, and goals to be crystal clear to everyone you're working with. You don't want a random agency you barely hear from once a month. You want someone who deeply understands your mission and can act on your behalf - build a strategy, execute it, and understand it as if they're a true member of your team.
That alignment gives you peace of mind knowing someone else also has your goals in mind. But it also helps your bottom line because you're not wasting time, money, and effort trying to wrangle a bunch of disconnected agencies when you don't have the expertise, leadership, or bandwidth to do that well.”
Here’s How You Know if You Need an Outsourced Marketing Director Like Madeline
I asked Madeline this question as it’s a question I see people ask around the spaces of the internet and it’s everyone’s question when it comes to hiring someone new. How do we know it’s time?
Madeline broke it down for us into 3 specific scenarios as to when we might need to hire an outsourced Marketing Director or strategist.
Scenario 1: You Already Know, But You Lack Resources
Madeline says that she has plenty of clients that come to her and they know it’s time to invest in marketing and they know who they need is a marketing director. These people typically really want to hire someone in-house, but they either:
Don’t have the time, money, or skill to manage someone who would be their direct report.
They don’t have the budget to hire a senior level marketing director who would also need an entire team in order to execute any strategy.
Scenario 2: You’ve Invested in Agencies, But It’s Not Working
This is you if you’ve invested in marketing, perhaps an agency or two, but you aren’t seeing results. You most likely don’t understand what the agency you’ve hired is doing or how what they are doing lends to your big picture. You’re not even sure if they understand you or what you need and want.
When it comes down to it, you have:
No central strategy
No transparency or trust
A lot of frustration
Scenario 3: You Have No Time, No Desire, and Maybe Even No Clue
No shame here, this is probably closer to where I’m at. There comes a time when we all have to realize we can’t do it all if we want to keep growing. This is you if you struggle with playing the waiting game (def my prob!).
If not seeing immediate results makes you want to throw in the towel, this is you. You’ve tried every platform, tried paid and organic marketing, you’ve done content marketing, and you’ve even tried networking, but it’s all half-assed because you just don’t have the time and haven’t been ready to give it up.
What it Looks Like to Work With Madeline
When you hire Madeline as your marketing director, she gets straight to work. First, she will help to audit and evaluate what is happening right now in your marketing. She’ll find out what your goals really are (not just at the base level!) and determine where you should focus your efforts.
A Broader Look at Madeline’s Process
When Madeline works with her clients, the main goal is to figure out what’s working and what’s not. Then you will run small experiments before you build your strategy to understand what your audience wants and what works for you.
Once you’ve done all that, then Madeline will help you build a strategy that you will work together to refine over a period of 3-6 months. At the end of that time period, you will know what works well for you and then you have the option to expand on that or even scale back because you already know what actually works.
Mistakes Small Business Owners Make When Outsourcing Marketing
Besides looking for an instant answer, Madeline and I see a number of mistakes small business owners make when delegating their marketing. I think it’s important to see both the side of a marketing director and an online business manager, as we have both seen all types of scenarios. Anyway, here are just a few:
#1 They Lack Clarity
Regardless of who you’re hoping to hire to help with your marketing, they need to fully understand:
your messaging
what you’re asking them to do
how what you’re asking them to do fits into your overall strategy
Without clarity on your part and the part of the person you’re outsourcing to, there is bound to be confusion and dissatisfaction on both sides. Speaking from experience, a VA or an OBM (or anyone!) cannot create what you’re looking for if they don’t really understand what you’re looking for and how what they are creating works with your marketing system.
#2 They Lack Context
Maybe you have the messaging down and can explain it incredibly well and your support person gets it. But you are still struggling with sharing important information with whomever will be doing a large part of your marketing.
To give your support person good context, you need to clearly explain to them:
Why you want to do the type of marketing you are doing.
Why you want help with your marketing.
Your desired audience.
Your desired outcomes.
Your goals for each marketing type and channel.
Your brand voice.
Plus, you need to:
Set clear, realistic metrics (and plan what will happen if you do and don’t meet them).
Check-in with your support person regularly.
Treat your support person like a true partner and not just as a task doer.
#3 They Lack Realistic Expectations
This one is so big. Expecting one person to do everything is not realistic. Unicorns are mythical in the wild; they also do not exist in VA, OBM, or Marketing Strategist/Director form.
No person, even a highly skilled professional, is going to be able to come in and completely do your marketing without spending some time with you and getting to know you and your brand.
Likewise, a single person is not likely to be able to handle every single thing you need, even the best in the world. And if they do handle it all, it likely won’t be what you are looking for because they will be more of a generalist with some knowledge in a lot of things than a specialist with lots of knowledge in one thing.
The best way to avoid this mistake is to understand who to hire and when. Here are some quick tips from Madeline and me:
If You're Hiring a Marketing Professional (like Madeline):
Madeline’s Thoughts:
You're investing in a higher level of expertise and strategy and you’re doing it upfront. She will work alongside you to help you narrow down what actually needs to be done, build a roadmap, and then manage the execution.
My Thoughts:
As a former VA and a current OBM, I highly recommend you do this before outsourcing your marketing to an OBM or a VA so that the OBM or the VA are extremely clear on what your goals are and so are you. It makes the entire relationship so much smoother and reduces friction in the relationship when we have a plan with goals and steps.
If You're Delegating to an Assistant or Operations Support Person (like a VA or OBM):
Madeline’s Thoughts:
You need to be really clear and transparent with them about what you need, what metrics you're hoping to see, and why you're investing in that particular area. Rely on them for guidance in their specific zone of expertise, they're the ones who can drive that area forward, but it needs to align to a wider strategy that you, as the business owner, have the responsibility to drive forward through their efforts.
My Thoughts:
It’s perfectly normal for it to take a few weeks (sometimes more) for a new person to master your brand voice, aesthetic, and style depending on how often you post, the type of content you’re looking for, and how complex your strategy is.
Be patient and don’t try to throw in the towel too quickly.
Give as many examples as possible.
Review their work heavily and consistently in the beginning to help them learn what you are looking for.
Be sure to share both the things you like and the things you dislike.
Be EXTREMELY specific.
Don’t be afraid to be honest about what you do and don’t like. If they don’t know, they can’t fix it.
Conclusion/Final Thoughts
Marketing, in some shape or form, is one of the biggest frustrations I see with clients and people in my audience. And as a fellow business owner, I totally get it! It’s time-consuming, takes longer than we’d like to master, and is sometimes all consuming. Despite all that, marketing is how we reach our customers and if we are not reaching customers, we are not making money.
No Marketing = No Business
It’s important to invest in your marketing early so you have a basis for your business rooted in clarity early on. Waiting is often the worst thing you can do because when you wait, you’re likely to find yourself desperate and unsure of how to get more customers. If you have a plan early on, you always know what to do next.
Meet Madeline Willett of Aligned Marketing
Madeline Willett is the founder of Aligned Marketing and works as an External Marketing Director for small and medium-sized businesses. She helps mission-driven organizations build marketing strategies that actually get implemented, without the overwhelm, guesswork, or full-time salary. Learn more at madelinewillett.com.
Are You Madeline’s Next Client?
If you’ve been reading through this and thinking “Oh, my God! I need a Madeline in my life,” she has some space for organic-social-only clients in the beginning of 2026. She and her team will create your social media strategy and execute it for you!
Word-for-Word Interview with Madeline Willett
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I help small and medium-sized business owners who don't have in-house marketing leadership get director-level marketing strategy and implementation without the full-time hire price tag (or headache).
Essentially, I step in as part of your team, someone who deeply understands your business, your goals, and your mission, and applies all of that through a marketing lens. I help you build a strategy and plan that actually makes sense for your business, and then I make sure it actually gets done by managing the implementation myself (with my team) rather than you juggling a bunch of different agencies or trying to DIY it with your already-stretched team.
Think of me as your outsourced Marketing Director: all the leadership, clarity, and execution you need, without having to build an entire department from scratch.
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I see this all the time, too. Marketing gets pushed to the bottom of the priority list because it feels expensive, uncertain, or like something only "big businesses" can afford. But here's the thing: marketing is literally how you get your message into the hands of your customers. If that doesn't seem like the most important part of your business... well, I'd love to learn about this magical business model that doesn't require customers! :)
The reality is that every business needs customers, which means every business needs marketing, whether you're small, scaling, thriving, or struggling. I get why people hesitate. It takes time, effort, skill, and yes, investment to do it well. But I think people assume they need to have all the answers or know exactly how it works before they get started. The truth? That's exactly why you need marketing support early on.
Marketing is a process of experimentation. You define a strategy, carry it out, and then evaluate what worked and what didn't. You experiment, optimize, and eventually land on marketing that serves you well, delivers ROI, attracts the right customers, and creates a clear customer journey. But none of that happens if you ignore it or wait until you're desperate.
Here's what I recommend instead: figure out what you can allocate toward marketing, understanding that results won't be immediate and that what your competitors are doing (or spending) doesn't necessarily translate to what will work for you. I can run the same marketing strategy for two different competitors and have it perform completely differently. That's because there are different brand elements, audience nuances, leadership styles, and sales processes at play. Marketing isn't one-size-fits-all.
Waiting until it's already too late; when you're desperate for customers and have no budget left - is obviously not the time to start experimenting. text goes here
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Great question! Part of why I started Aligned Marketing is because I saw a real challenge when I was working as a Marketing Director inside small businesses. I'd watch myself and others either struggle to implement everything ourselves or we'd hire a bunch of different agencies - but we'd lose transparency, context, and alignment in the process.
Those agencies were managing tons of clients. They weren't involved in our day-to-day. They didn't always understand our goals clearly - and it wasn’t their fault! And we'd spend so much time explaining context, chasing updates, or trying to figure out if what they were doing even tied back to our bigger picture.
So I saw this gap where I could step in and help businesses that needed director-level leadership, someone who could actually bring together the teams, the knowledge, and the strategy so everything was aligned. Not just "aligned" in a fluffy way, but aligned in a way that meant we weren't accidentally spending money in areas where we didn't understand the ROI, and we weren't constantly re-explaining our mission to people who should already get it.
This is especially important for mission-driven organizations. You want your values, priorities, and goals to be crystal clear to everyone you're working with. You don't want a random agency you barely hear from once a month. You want someone who deeply understands your mission and can act on your behalf - build a strategy, execute it, and understand it as if they're a true member of your team.
That alignment gives you peace of mind knowing someone else also has your goals in mind. But it also helps your bottom line because you're not wasting time, money, and effort trying to wrangle a bunch of disconnected agencies when you don't have the expertise, leadership, or bandwidth to do that well.
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The breaking point usually looks like one of three scenarios:
Scenario 1:
They know they're ready to invest in marketing, and they want to hire someone in-house, but they either don't have the time, money, or skill to manage a junior hire, or they don't have the budget to hire someone senior who would then need an entire team to execute.
Scenario 2:
They're already working with a handful of agencies, but they're not seeing results and they don't really understand what those agencies are doing or how it all ties together. There's no central strategy, no transparency, and a lot of frustration.
Scenario 3:
They don't understand that marketing is an experiment that takes time, so they're not seeing immediate results and they're ready to give up. Or they're spread way too thin - trying to be on every platform, doing paid and organic, content marketing, email marketing, referral programs - and because they're stretched so thin, they're doing it all poorly.
When I come in, I help audit and evaluate what's happening now, what their goals truly are, and where we need to pull in focus.
What you need is to identify what's working and what's not, run smaller experiments upfront, and build a strategy that we can refine over the first 3–6 months of working together. Once we know certain foundational elements are working well, then we can expand (or we can scale back and invest even less time, energy, and money because we've nailed what actually moves the needle).
Basically, if you're feeling overwhelmed, confused, or frustrated by your marketing, or if you're about to hire someone and you're not sure what they should actually be doing, that's the time to bring in strategic support. Waiting until you're burned out or broke just makes the climb back up that much harder.
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This is such an important question, and here's the key: if you're hiring someone with a specific skill - whether that's a VA, an OBM, a social media manager, or an email marketer - you need to be crystal clear about what your messaging is, what you're asking them to do, and how it fits into the larger strategy.
Too many people hire someone and assume that one person will magically handle everything, even when they're not a generalist. That's just not realistic.
Here's what you need to do instead:
If you're hiring a generalist (like me): You're investing in that level of expertise and strategy upfront. I help you narrow down what actually needs to be done, build the roadmap, and then manage the execution.
If you're delegating to a specialist (like a VA or OBM): You need to be really clear and transparent with them about what you need, what metrics you're hoping to see, and why you're investing in that particular area. Rely on them for guidance in their specific zone of expertise, they're the ones who can drive that area forward, but it needs to align to a wider strategy that you, as the business owner, have the responsibility to drive forward through their efforts. .
The biggest mistake I see? People delegate tasks without context. They hand off "post three times a week on Instagram" without explaining why, who the audience is, what the goal is, or how this ties to the business's bigger picture. That's a recipe for random content that doesn't convert.
If you want your VA or OBM to stay true to your marketing strategy, you need to give them the strategy in the first place. Share your goals. Share your brand voice. Share your audience insights. Set clear metrics. Check in regularly. Treat them like a true partner in the process, not just a task-taker.
