The top 3 marketing challenges for small businesses (and how automation can solve them)

Caroline Burk

Updated: Mar 06, 2024 · 8 min read

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Do you ever wish you had a crystal ball to predict future problems in your business? If you could know what to expect, you could prepare better and maybe even smother fires before they start.

We can’t see into the future to tell you every hurdle your business will have to overcome, but we did some research to help you out. We recently conducted a survey of 500 entrepreneurs, CEOs, and sales and marketing experts to gather data about their paths to success, along with the missteps they’ve made along the way.

Their responses revealed some impactful data, including the top marketing challenges small businesses face.

In this article, we’ll cover those challenges and dive into actionable solutions, so you can anticipate them and breathe a sigh of relief.

Challenge one: Developing content for my marketing efforts

Your marketing efforts should never stop, which means you and your team constantly need to come up with new campaign ideas and content. And to engage your audience and increase conversion, that marketing content has to be fresh and interesting. So, what happens when you hit a wall in your creativity?

Many small businesses are facing this exact struggle. In fact, this is the number one marketing problem small businesses are dealing with according to Keap’s State of Business Growth in 2024 report.

If you’ve ever dealt with this, take heart that you’re not alone and take note of these content generation tips that can alleviate creative dry spells:

AI tools

Maybe you’ve tried using AI to develop content, but are you asking the right questions? AI takes time to train, and it won’t always produce the greatest results right off the bat because it doesn’t know your niche.

Start by telling your AI tool about your business, your mission, your product or service, your target market and any other relevant details. You can even talk to AI about past marketing campaigns — what you liked, what you want to change and the results. The more information you provide, the better results you’ll get in return. AI also improves the more you use it, so ask questions, get specific and use it often!

ChatGPT is a popular AI service if you don’t have one yet. You can also opt for a service built into your small business CRM and automation software. Keap’s AI Content Assistant was built with small businesses in mind, which means there’s less training to do on your part.

Tap into unexpected resources

Is your marketing team working on an island? You’re more likely to run out of content ideas when you’re brainstorming in a vacuum. So, step out of your comfort zone and mix it up.

One easy way to do this is to chat with other departments to get their fresh perspective. Sales is a great place to start. They know the questions your prospects are asking and what features of your product or service are most interesting to your audience. Knowing this information will narrow your topic choices, and once you know the subjects you should focus on, you can use them as launching points for your marketing campaign content.


There’s no shame in repurposing content. It’s strategic to use things you’ve already created to help spin off some new marketing assets. For example, if your team made an ebook last year and you’re lacking blog content, choose a chunk of that book to expand upon in a blog post. This way, you’re not repeating content and boring your audience. Rather, you’re giving them more context and answering any follow-up questions they might’ve had.

Another idea is to repurpose content into a lead magnet. Try reworking a series of blog posts into a guide, or make a downloadable graphic or list from a YouTube video you made. Repackaging content in new ways is a great way to reengage your audience and attract new leads. Plus, it’ll save you and your team time.

Challenge two: Differentiating my business from competitors

Setting your business apart from the competition has probably been a focus from day one of your entrepreneurial journey. Our recent trend report shows that this goal doesn’t dissipate as your business grows, and it was the second most common challenge for small businesses of all sizes.

To stand out within your niche in a positive way, there’s a formula:

Dynamic content + CRM + Small business automation = A customized experience for every contact

Let’s be honest — you have a lot of contacts in your database. There are way too many leads and customers for your team to personalize every piece of content manually. You need the help of dynamic content, a small business CRM and business automation.

Dynamic content

Dynamic content allows you to customize content based on the specific information you know about your audience. Popular ways to employ a dynamic content strategy are with web pages, emails and ads. You can tweak these marketing assets to have personalized CTAs, images and copy based on who the audience is.

For example, you may have a new offer going out to your email database, but instead of bulk sending the same message to your entire list, you could segment your contacts between past customers, new leads and existing clients, or by other demographic details. Then, send each group a message tailored to their specific buying situation.

Small business CRM

Dynamic content is nearly impossible to pull off without a small business CRM. This software stores and organizes the data you have about your contacts, which you need to customize content. A good CRM will enable you to automatically capture new lead information, segment your list and tag specific contacts based on their actions. It’s not feasible for you to manually store and organize all audience information on your own, so these features are a must.

Business automation

It’s also not realistic for you and your team to send every personalized piece of content manually. There’s a quicker way to get it done using small business automation. Your business automation software should integrate with your CRM so it can access your segmented contacts. Then, the magic happens when the software automatically sends your audience relevant emails and texts as they move through your sales pipeline.

Another feature to look for in your business automation platform is the ability to create one email and easily populate different sections of that email with specific content based on audience segments.

When dynamic content, CRM for small business and automation work together, your audience gets the right message at the right time with personalized content they want to read. Making your prospects and customers feel seen and understood is what it’s all about, and that’s exactly what will make your business stand apart from the rest.

Challenge three: Filling my sales pipeline consistently

It’s hard to stay optimistic about your growth when you’re struggling to collect quality leads. So it’s understandable that consistently filling the sales pipeline made the top three marketing challenges reported by small businesses.

Fortunately, there are plenty of strategies at your disposal that can give your pipeline a boost. You should start by evaluating the following four items:

  1. Ideal customer - If your sales pipeline isn’t predictable, you might have the wrong buyer persona in mind. And if you have the wrong persona, you won’t know how to effectively communicate with them, and your marketing campaigns will fall flat. You may need to reevaluate who your ideal customer is, and the key to this is to get specific. One way to narrow your options is by creating a customer avatar. This requires you to define demographics, psychographic traits and other information. Read more in our blog about designing a customer avatar.
  2. Referral process - Are you consistently asking for referrals? If not, you’re leaving leads (and money) on the table. When a customer has had a great experience with you, they’ll be happy to leave a review or refer a friend who could use your services. Be ready to jump at this chance by having an automatic referral and review process in place. A CRM and business automation software can help by automatically reaching out to customers after the purchase.
  3. Lead capture forms and landing pages You may be struggling to consistently fill your sales pipeline if you’re not taking every opportunity to capture lead information. This is when a CRM for small business can really shine by automatically capturing and storing any information you need from your audience. Make sure you have lead capture forms and landing pages on every platform. For example, you can include a landing page or form in your social media bios, craft a form for people to fill out before downloading a free resource or registering for an event, and so much more. There are endless ways to use landing pages and forms to gather the information you need, so look for a CRM that offers a robust set of templates and user-friendly features to make this process easier.
  4. Voice and messaging - Finally, make sure you’re crafting effective messages for your audience to encourage them to act and enter your sales pipeline. Donald Miller’s storytelling framework is one tried and tested method that’s shown real conversion results. It’s six steps, and you can use it anywhere you communicate with your audience.

More small business insights you can use to scale

If you’d like to dive into more small business insights and get action plans for addressing specific challenges based on your business’s size, check out our free State of Business Growth in 2024 report. You’ll find 2024 trends, data, and honest advice about the triumphs and trials of over 500 entrepreneurs, CEOs, sales pros, COOs and marketers.

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