Do you own or run a well-established legacy business? Have you always relied on organic growth and great customer service to achieve success?
If so, how is this working for you in the modern era?
Is it enough to sustain your next phase?

In my more than 15 years of marketing, I’ve worked with some truly amazing businesses that boast rich histories and impressive legacies carved out over more than 20 or 30 years of operation.
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Typically, over this time, these businesses have always found themselves in high demand, allowing them to grow organically through a combination of passion and dedication to their craft and customer service.
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Of course, this is extremely admirable, and a testament to the hard work of everyone involved!

However, one thing I often notice when working with these legacy businesses is that they are all facing the same common challenges, even when, on the surface, nothing seems particularly wrong.

The mature business challenges I’m talking about here include:

  • Organic growth has worked over time but there’s now a sense of “winging it”
  • Misalignment between the sales and marketing functions
  • One or two staff members hold the majority of business IP inside their head
  • There are no systems in place to transfer knowledge when key staff leave
  • The overall brand no longer reflects the business’ service offering
  • The business doesn’t have a clear marketing strategy

Do any of these sound familiar to you?

You’re certainly not alone.

The reality is, though, while your business is still trundling along well, none of these background challenges may seem immediately problematic or urgently needing your attention, right?

But what happens when:

  • it comes time for you to sell?
  • a key staff member decides to retire or move on?
  • organic referrals start to slow down?

All of a sudden, these challenges can become a very real and immediate issue for your business.
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As a Fractional CMO, I see this every day.

But don’t worry – you haven’t done anything wrong.

All of this is not to say that your business is doomed.
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In fact, while you may or may not have noticed a bit of a growth plateau, you’re likely still heading in the right direction.

But what’s most important is that now is the ideal time to start thinking about how to tackle these challenges head-on to breathe new life back into your legacy business and help elevate your brand to where it truly deserves to be.

Does this sound like a good idea?

Great, I’ve got you covered. Let’s solve them all.
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In this article, I’ve outlined the 5 most common problem scenarios that I see legacy businesses grappling with in the modern era – scenarios that are a direct result of the challenges outlined above.
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To help make sure these don’t happen to you, I’m going to provide you with the practical solutions you need to successfully navigate each scenario and strengthen your business for years to come.

Table of Contents

The Risks of Misalignment in Legacy Businesses: Key Problem Scenarios

  1. When It’s Time to Sell the Business
  2. When Your Staff Decide to Leave or Retire
  3. When Organic Referrals Slow Down
  4. When Your Brand Doesn’t Reflect Your Business
  5. When Your Sales and Marketing Are Not Aligned

What is a Fractional CMO?
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Why does this work so well for your business?
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What does a Fractional CMO do?
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Do you need help with aligning your legacy business’ sales and marketing function?

The Risks of Misalignment in Legacy Businesses: Key Problem Scenarios

While the challenges I mentioned above may not be directly impacting your business right now, there are several common scenarios most legacy businesses find themselves in that, once they arise, will eventually make these challenges much more prevalent and difficult to navigate.
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For this reason, I always suggest tackling these challenges and integrating the right solutions as soon as possible to avoid running into much larger problems further down the road.
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Let’s start with one of the most common problem scenarios that every legacy business owner will eventually face.

1. When It’s Time to Sell the Business

Every business owner will eventually look to sell their business at one point or another.

When this time comes for you, potential buyers will want to see that your business’ marketing and sales function is running profitably, with well-embedded systems, processes and teams – a stability that’s often reflected in consistent acquisition, revenue and retention rates.

This means that developing and implementing a clear marketing strategy is essential to helping demonstrate this stability and alignment.
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Without doing so, your business may appear as a risky, over-valued or less attractive investment to potential buyers.
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Let’s face it: no one’s going to look twice at a less-than-sound investment.

The solution:

Even if you’re not ready to sell for another 5 or 10 years, now is the ideal time to start setting your business up to be a worthwhile investment.
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Don’t leave it until it’s too late! Try this:

  • Begin with a holistic Strategy, which involves assessing where you are now and where you want to get to, and then determining what your business needs to do to get there.This includes streamlining your operations and creating a robust marketing strategy that makes your business appear far more attractive to prospective buyers.

For more on this, see my Ultimate Guide to Building a Digital Marketing Strategy in 2024.

  • Next comes aligning your Marketing and Sales functions so they are united in driving revenue more efficiently.
  • From here, start regularly measuring the performance of marketing initiatives implemented, ultimately striving to be able to demonstrate a proven track record of measurable business & marketing success.
  • Finally, engaging an expert Fractional CMO like me can help with evaluating your existing systems, identifying gaps and implementing the right tactics to ensure true business alignment and efficiency – all without increasing your headcount!

As a Fractional CMO, I can bring an external perspective to your organisation to help.

2. When Your Staff Decide to Leave or Retire

Another challenging issue many older businesses often face is the loss of institutional knowledge when key staff members decide to leave – and the subsequent disruption this creates for your sales and marketing efforts.
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This institutional knowledge, often stored in the minds of founders or long-tenured employees, typically includes critical operational and strategic insights that your business cannot do without!

This means that, as these key team members look to retire, move on and change careers, you need to make sure you’ve got a way to get this institutional knowledge out of their heads so it can be easily transferred to others.

In other words, you need to start documenting this information and ensuring it’s trainable to others to help maintain crucial continuity in your business.

The Solution:

While most people assume all of the critical business knowledge will remain in their organisation, it’s important to ensure it by:

  • Identifying the key stakeholders who have access to specific information such as procedures and best practises.
  • Encouraging them to record & document all regular processes as well as their insights, innovations and ideas, plus train other colleagues so this knowledge can be shared.
  • Saving this information and making it accessible to the whole team so that this knowledge is never lost, no matter what happens in the future.

Unfortunately, this can be quite overwhelming in practise.
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That’s where a Fractional CMO like myself can work closely with your teams to document, polish and systemise this key information and ensure it will always be accessible and trainable to others – even after those critical staff members leave the business.
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Not only will this help to safeguard your valuable business knowledge, but it will also help to enhance your business’ value when the time comes to sell as well.

3. When Organic Referrals Slow Down

Here at Ask Marketing, I’ve found that so many of the legacy businesses I work with typically rely on an organic referral system to help bring in the bulk of their revenue.

While this should be considered a testament to their customer service, professionalism and reputation in their industry, the reality is that it’s not unusual for these organic referrals to slow down – especially as the market changes, customers evolve and technology shifts over time.

Of course, any slowdown in these organic referrals can typically be attributed to various issues within lead generation and sales pipelines.
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For example, this is something that often occurs when your brand no longer accurately reflects your business’ current offerings or market position (more on this in a minute).

The Solution:

To ensure that leads and revenue continue to flow into the business from a diverse number of sources, it’s important to take action now before referrals potentially dry up.
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This involves:

  • Reviewing your Sales Strategy to assess its effectiveness in converting leads into proposals and proposals into paying customers.

For more, read: Not converting 70% or more of your proposals into customers?

Working with a Fractional CMO like myself can help to revitalise your brand and digital marketing strategies to realign them with your business’ current state and target audience.
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As part of this process, I can set up new marketing systems, optimise your digital presence and ensure your brand resonates with the modern customer – thereby boosting your referrals and lead generation overall.
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Of course, setting up these types of new marketing systems takes time.
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That’s why it’s important not to wait until your organic referrals dry up to start investing in alternative lead-generation strategies.

4. When Your Brand Doesn’t Reflect Your Business

As your business evolves, your service offerings may change significantly over time.
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That’s why it’s essential to ensure your brand identity always remains aligned with these changes to reflect your company’s current capabilities and market focus.
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Failure to do so can lead to a considerable disconnect between your internal capabilities and external perceptions – which, as I mentioned earlier, can then lead to a reduction in organic referrals.

Think about it this way: if your website and branding say you do X, but over time, your business has evolved to now do Y and Z, then potential customers are only going to wind up confused and reluctant, which will dramatically impact your business’ success.

The Solution:

If you have an inkling that you’re facing this (and don’t worry, you’re not alone), then the best way to address this is:

  • Have a good relook at both your visual and written branding. Do you feel that they accurately portray what your business stands for today?
  • If not, then it’s time to take action. This involves circling back to how your brand looks and communicates, and updating both to more align with your current and future positioning.

Finally, you want to develop a Digital Marketing strategy that can put those new branding elements into action effectively.

If you need help, a Fractional CMO like myself can come into your business, assess your current brand perception, identify areas of misalignment and craft a refreshed brand strategy that accurately represents your business in the modern era.
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Doing so will realign your brand and your business to help prevent customer confusion and strengthen your company’s market position.
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Of course, this doesn’t mean you have to do a complete brand overhaul. It’s just about asking whether your brand genuinely reflects your current service offering and environment.
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When everything is well-aligned, this can be incredibly powerful in cementing your place in the market for many years to come.

5. When Your Sales and Marketing Are Not Aligned

The alignment of your sales and marketing is critical for a cohesive business strategy.
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Often, I see legacy businesses operating with an ad-hoc and traditional approach to sales and marketing that typically looks like:

  • Strictly focusing on business development activities
  • Attending events and trade shows
  • Investing in branded banners, etc.

As these businesses grow organically, however, their team members start to wear many different hats, and several misconceptions begin to form around what sales and marketing should do and be.

For example, some businesses I work with have always focused on sales and genuinely don’t understand the need for marketing, as what they are doing is already working. What they don’t realise is that this is essentially like fighting with one hand tied behind your back.

Overall, this approach leads to a lack of focus on long-term strategies like acquisition marketing, retention marketing or account-based marketing.
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Here at Ask Marketing, we’re big advocates of the idea that sales and marketing should not be treated as two separate departments, but rather as one well-aligned function.
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So, how can your legacy business realign your sales and marketing?

The Solution:

Well, again - you probably guessed it - it’s about:

  • Starting with a Digital Strategy. You see, putting this together gives you a compass that can help pull together your different business functions.

For more, read Strengthening Sales: 10 Account-Based Marketing Techniques for Acquisition and Retention.

  • Then, once you’re ready to implement this strategy, it can be helpful to have a Fractional CMO come in to work alongside the sales team to drive positive change.

For instance, a Fractional CMO like myself can conduct a comprehensive assessment of your current sales and marketing practices before developing a unified strategy and implementing the right processes to foster collaboration and synergy between your teams.
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By taking the time to realign your sales and marketing, this will ultimately help to enhance your customer experience and drive business growth now and into the future.

What is a Fractional CMO?

Okay, I get it.
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You’ve heard me talking about a Fractional CMO for this entire article now. But what exactly is it?

In a nutshell, a Fractional Chief Marketing Officer (CMO) is a seasoned marketing leader who works on a flexible basis to help your business set up and optimise your marketing strategies.

We bring extensive experience to the table and can tailor our involvement to meet your company’s specific needs. By leveraging our expertise, your business can:

  • establish a solid foundation
  • address critical challenges
  • strengthen your sales and marketing
  • revive your business trajectory, and 
  • position yourself attractively for potential buyers.

Here at Ask Marketing, our Fractional CMOs, including myself, have more than 20 years of marketing experience, and we can work to fit around your business schedule to provide you with all the benefits of an in-house marketing leader without the expensive costs.

Why does this work so well for your business?

As a Fractional CMO, I can come into your business once or twice a week, execute your digital marketing functions and set up the strategies you need to get the momentum going, before handing over to your team to carry it on long after I’m gone.
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In this way, you’re getting the best of both worlds!
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You’re getting my years of expertise and fresh perspective while also empowering your teams to put the right systems in place so your sales can work seamlessly with your marketing, and vice versa – ensuring your continued business success for years to come.

What does a Fractional CMO actually do?

As an expert Fractional CMO, I will come into your business and:

  • Manage the successful rollout of your marketing strategy
  • Manage all team members and/or agencies involved in execution each month
  • Sit alongside and work with your head of sales and senior leadership team
  • Manage your marketing function – from people to marketing content to tools

Sounds too good to be true, right?
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Luckily, it’s not!
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So, if you’re looking for a cost-effective marketing leader to take marketing management off your plate and offer fresh, objective advice to your legacy business, all you have to do is ASK!

Do you need help with aligning your legacy business’ sales and marketing function?

At Ask Marketing, we act as an outsourced Chief Marketing Officer, offering a managed marketing solution to help B2B service-based businesses build demand, establish thought leadership and own their industry through digital business marketing.

Stop waiting. Start building. And land your dream client!

Just get in touch with us and we can discuss your business and the ways we can help you with our Fractional CMO service today.

Together, let’s solidify your sales and marketing function and achieve your business goals!

For more great marketing content, connect with company leaders, Alexandra King and myself, Stephanie King, or follow our Ask Marketing LinkedIn page.

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Stephanie King

Stephanie brings campaign management and senior analytical capabilities to dissect multi-channel data, providing actionable marketing insights and driving optimal business performance.