Don’t Let Marketing Be Your Weakest Link

Matt Buckley By: Matt Buckley

Back in March, Mainsail Partners published its 2018 Bootstrapped Sentiment Survey, providing insights into trends affecting growth stage software companies. As part of the survey, we asked respondents to report on what they view as the strengths and weaknesses of each functional area of their business. We also asked which best practices they are implementing for each function.

Now, we’re digging deeper to understand how certain best practices differentiate self-identified strong and weak marketing teams.

Marketing — why is it the weakest link?

Only 2% of the entrepreneurs we surveyed view marketing as the biggest strength of their business—the lowest of any functional area. What’s more interesting, fewer than 42% have a marketing leader in place and only 9% view marketing as the function that is currently most important to them.

This isn’t entirely surprising, given that bootstrapped software entrepreneurs are often product-driven in nature and tend to focus on funding operations and technology before brand-building. However, marketing is an essential component of growth.

Of the companies we surveyed who view marketing as a strength, we found they align on three key best practices:

  • Develop buyer personas, value proposition and messaging framework
  • Clearly define marketing qualified leads and hand-off to sales
  • Specialize marketing team to scale (brand, field, demand gen, product marketing)

Let’s dig a bit deeper into each best practice.

Understand your target audience

Many early-stage company marketing teams rely on the tribal knowledge of their founders to understand their target audience. But as a company grows, we find it’s important to operationalize the process by defining your buyer personas, value proposition and messaging framework in a way that’s actionable and scalable. According to the Bootstrapped Survey, 80% of companies that view marketing as a strength completed this work; only 30% of companies who view it as a weakness did so.

80% of companies that view marketing as a strength have developed clear buyer personas, a value proposition and messaging framework.

To get started:

Define your buyer persona. Interview your most successful customers or prospects in your most important market segment. What are their pain points? What do they view as a successful outcome? What does their boss care about? Understand the typical background of your ideal customer, as well as their motivations and priorities. The more detailed your persona, the more relevant your marketing.

Define your value proposition. Conduct research internally and across the competitive market to understand what differentiates you. Are you the premium, expensive product with the deepest functionality? Or the lightweight, inexpensive option that’s easy to use? Avoid the temptation to be overly aspirational; your value prop should be research-driven and authentic.

Define your key messages. Develop a set of key messages per persona aligned with each of their unique pain points. Reinforce these messages through clear, consistent and highly targeted campaigns.

These exercises can help make the difference between a strategic approach to marketing and a see-what-sticks approach. With a common language and a clearly defined target audience, your marketing team may be able to cheat the economies of scale enjoyed by larger companies.

Align objectives for marketing and sales

Though marketing and sales share the same objective—to generate growth—the functions have different approaches and sometimes operate within different incentive structures. This lack of alignment can lead to friction between the teams and long-term inefficiencies for your company.

You can combat this by aligning your metrics for success. Of the companies we surveyed, 60% of those who believed marketing is a strength measure marketing based on the percentage of pipeline and closed deals they generated. By comparison, only 25% of those who view marketing as a weakness measure this way. If marketing can learn to speak the language of dollars and cents—as opposed to vanity metrics like page views or followers—you can greatly improve their alignment with sales.

It’s equally important to clarify the roles and expectations of each function and the hand-off between the two. Marketing should be crystal clear on when to pass a lead to the sales team, for instance, and sales should be just as clear on expected follow-up.

If marketing can learn to speak the language of dollars and cents—as opposed to vanity metrics like page views or followers—you can greatly improve their alignment with sales.

Know when to specialize

Finally, think about the people who make up your marketing team. Your first marketing hires should almost always be generalists: marketing professionals who know a little bit about a lot of disciplines and who are comfortable wearing several hats. Support them with outsourced talent (freelance designers, copy-writers, ad agencies, etc.), as you grow through your first few million in revenue.

When you hit the $5M–$10M revenue mark, consider specializing. 60% of entrepreneurs who say marketing is a strength are specializing their hires; only 19% of those who feel marketing is a weakness do the same.

The key is not only knowing when to specialize but with whom.

Start by identifying the highest performing channels for your company and hire a specialist who can double down on that success.

Let’s say you’ve been working with an ad agency to run an AdWords campaign and it’s proven to be an effective channel of acquiring new customers. Throw fuel on that fire by hiring a performance specialist. Or, let’s say your product is extremely technical or you’re in a particularly competitive market and you need help conveying your product’s functionality and differentiation. Hire a product marketing manager.

The ultimate goal should be to transition from a small team of multi-taskers to a larger team of specialists who can take you through the next phase of growth.

Start somewhere

It’s common for bootstrapped companies to defer major marketing investments for as long as possible. But at some point, the need for marketing investment is inevitable. When you get to that point, use this guide to map your strategy. Of all the best practices we surveyed for, these three correlate most strongly with self-identified strong marketing teams.

If nothing else, it’s a great place to start.


Matt Buckley
Matt is a Marketing Director at Mainsail Partners. He works with Mainsail’s portfolio companies to implement marketing and sales technology to fuel growth.
More by Matt Buckley
This content piece has been prepared solely for informational purposes. The content piece does not constitute an offer to sell or the solicitation of an offer to purchase any security. The information in this content piece is not presented with a view to providing investment advice with respect to any security, or making any claim as to the past, current or future performance thereof, and Mainsail Management Company, LLC (“Mainsail” or “Mainsail Partners”) expressly disclaims the use of this content piece for such purposes.

The information herein is based on the author’s opinions and beliefs on marketing and related topics based on the 2018 Bootstrapped Survey. There can be no assurance other third-party analyses would reach the same conclusions as those provided herein. The information herein is not and may not be relied on in any manner as, legal, tax, business or investment advice.

Certain information contained in this content piece has been obtained from published and non‐published sources prepared by other parties, which in certain cases have not been updated through the date hereof. While such information is believed to be reliable for the purposes of this content piece, neither Mainsail nor the author assume any responsibility for the accuracy or completeness of such information and such information has not been independently verified by either of them. The content piece will not be updated or otherwise revised to reflect information that subsequently becomes available, or circumstances existing or changes occurring after the date hereof, or for any other reason.

Third-party images and logos included herein are provided for illustrative purposes only. Inclusion of such images and logos does not imply affiliation with or endorsement by such firms or businesses.

Certain information contained herein constitutes “forward-looking statements,” which can be identified by the use of terms such as “may,” “will,” “should,” “could,” “would,” “predicts,” “potential,” “continue,” “expects,” “anticipates,” “projects,” “future,” “targets,” “intends,” “plans,” “believes,” “estimates” (or the negatives thereof) or other variations thereon or comparable terminology. Forward looking statements are subject to a number of risks and uncertainties, which are beyond the control of Mainsail. Actual results, performance, prospects or opportunities could differ materially from those expressed in or implied by the forward-looking statements. Additional risks of which Mainsail is not currently aware also could cause actual results to differ. In light of these risks, uncertainties and assumptions, you should not place undue reliance on any forward-looking statements. The forward-looking events discussed in this content piece may not occur. Mainsail undertakes no obligation to update or revise any forward-looking statements, whether as a result of new information, future events or otherwise.

No representation, warranty or undertaking, express or implied, is given as to the accuracy or completeness of the information or opinions contained in the enclosed materials by Mainsail and no liability is accepted by such persons for the accuracy or completeness of any such information or opinions.