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The ultimate guide to building awareness for enterprise software, including marketing tips, social media strategy, and conducting user interviews.

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You’ve made it so far! Good job. To get the most out of this article, you should have already:

  • Defined your ideal customer profile (ICP)
  • Identified your target USER persona(s); researched and documented your USER/BUYER journey 
  • Developed a deep understanding of the USER’s pain that you’re solving and how your USERs research solutions to this problem 
  • Created your messaging and positioning and launched a marketing website
  • Mapped your USER/BUYER journey into your Modern GTM Funnel and identified key metrics for tracking funnel activity and goals

If you haven’t completed all of these things, you should read this content before you dig in too deep with awareness and education

• Introduction to the Modern GTM for early-stage founders
• GTM funnel stages, metrics, & goals

• Leads! How do we get more leads?
Crafting your story

Ah, awareness! The not-so-simple art (and science) of getting your ICP USERs to know you exist and that you offer a solution to their problem. Effective awareness activities and programs don’t just succeed in building awareness but also seamlessly transition USERs from awareness into the education stage of your funnel. I’m getting ahead of myself. First, let’s dig into awareness. 

Gaining awareness of your users so they can gain awareness of you

Before USERS can become aware of you, you must be aware of your USERs.

I know, that sounds all meta. But, it really is true. You’ve likely already spent a good amount of time with your USER persona population to learn about their challenges and gather requirements for your solution. Now it’s time to go back to those USERs to hear them describe their problems (related problems only, please) and learn how they research, educate themselves, and evaluate solutions. With this information in hand, you’ll be able to create the programs and tactics necessary to inject your company into the beginning stages of their journey.

How to prepare for USER interviews 

Prep step 1: Articulate (to yourself and co-founders) what you want to learn
Simply articulating that you want to learn how USERs gain awareness and educate themselves, while true, is way too broad. Instead, get detailed and specific. For example, ask USERs what error messages they get or ask them to do a Google Search for you and explain why they skip over certain results and click on others. 

Prep step 2: Understand and appreciate that most USERs will approach the interview very differently than you will
You’ll be excited and ready to extract as much information from them as you can. And they’ll probably be thinking, “Ugh, why did I agree to this? I’m so busy. If I keep my answers brief, maybe we can wrap this up in 20 minutes.” Your goal will be to ask the right questions, show that you empathize with their pain, and be nimble and adapt your questions based on what you’re learning.

Prep step 3: Sit down and write out the questions
Trust me, I’ve fallen into the trap of thinking, “I’m so busy and I already know what I want to learn — the questions will come to me during the interview.” Unfortunately, I know all too well that interviews I didn’t prepare for weren’t even half as effective as the ones that I prepared questions in advance. 

To be clear, having questions handy during the interview is helpful but not what makes it so much more effective. It’s the thinking, writing, rewriting, and pruning you do while preparing the questions that solidifies the information you really need to obtain. You may find that you only ask one or two of the prepared questions and that’s totally fine because you’ll be making a conscious decision to change course based on what you’re learning. In this case, you might recognize that the questions you prepared aren’t as valuable as this new course of questioning. 

Suggested questions to ask in USER interviews

The questions you ask will be highly dependent on the product you’re building, the hypotheses you’ve formed, and the personas you expect to interview. With that said, the interview generally has the following format:

A. Get grounded with overview questions, such as:

  • Tell me about your business. What products or services do you sell to your customers?
  • What is your role in the company? 
  • What are some of the high-level challenges you face in your role?

B. Learn more about about their challenge(s):

  • We’re an early-stage startup building a product that helps people like yourself do XYZ (better, faster, cheaper). How much time do you spend in your job focusing on these aspects? Does that seem like the right amount of time, too much, too little? 
  • What are the three biggest challenges you face in this area and how do these challenges impact you, your customers, and your team? On a scale of 1–10 — 1 being very little and 10 being catastrophic — how much do these challenges impact you personally? Your customers? Your company? 
  • How do you get around these challenges today? How much time do you spend dealing with these challenges on a daily/weekly/monthly basis?
  • What do you think is the right way to resolve these challenges? What’s the ideal solution?
  • If you could wave a magic wand and solve these challenges, how would things change for you personally, your customers, and/or your company?

C. Ask questions about how they like to learn about solutions to their specific challenges or their job function more generally:

  • What are your go-to sources for researching these types of challenges?
  • What is your preferred way to consume this kind of information:
  1. Blog articles
  2. ebooks/white papers
  3. Webinars
  4. Videos
  5. Discussion forums
  6. Conferences
  7. Meetups
  8. Peers and colleagues

D. What are your top five conferences or meetups that you attend?

  • Which online communities do you belong to or use frequently? Why are these communities your favorites?
  • Are there any influencers or experts in your field that you follow? Do you follow them on Twitter, Medium, other? 

3 tips for live USER interviews

  1. Ask follow-up questions

When a USER responds to a question with what seems to be a valuable answer, I find it helpful to verify that you understood them correctly. For example, I interviewed a data scientist USER about a problem they encounter that’s being solved by an Unusual portfolio company. Based on the USER’s response to a question, it appeared he was using an existing open-source library to solve the problem. 

When I asked, “Oh, so you’re already using that library and it works?” the USER said they’re not using it and explained, in detail, all the limitations with the open-source solution. This information was pure gold! The answer to my follow-up question reshaped our understanding of the USER’s pain, revealed limitations of existing solutions, and unlocked messaging and content opportunities for us. 

I used to avoid asking these kinds of follow-up questions because I thought I would appear unknowledgeable and didn’t want to weaken my credibility with the USER. But as far as I know, that’s never happened and I always learn so much from asking seemingly “dumb” questions. Here’s a more all-purpose example of how to weave in follow-up questions:

During an interview, a USER answers a question with A, B, C. I respond, “Let me see if I understood that correctly. What you’re saying is A, B, C?” and of course I’ve put their response in my own words. This often results in the USER responding like, “No, not exactly. What I meant was A, B, D.” hat minor difference is often a key piece of information that will be extremely valuable to include in your messaging and content.

2. Pay attention to lingo
Every field has its own lingo. When you’re talking with USERs, make sure to pay attention to the words they use and not just the concepts of their response. The words they use are likely to be the words they use when searching for solutions too! This will come in handy for SEO as you publish your website and other content. Using the proper terminology and lingo also helps build your credibility with users. 

3. Be nimble

As you’re interviewing you may find that you need to adapt your interview questions or approach. This is a good thing and part of the learning process. To get the most out of upcoming interviews, update your list of questions based on learnings from the interviews you’ve already completed. 

5 common ways that USERs look for solutions to their problems

• Google Search 

• Social media and influencers

• Specialized communities

• In-person events

• News and podcasts

1. How to optimize your content for Google Search (and other search engines)

So, you want to rank No. 1 for the most relevant keywords to your solution on Google — who doesn’t? The good news is that there’s no shortage of articles, tools, and vendors out there to help an SEO novice get up to speed quickly. Google it! See what I mean? That’s why I’m not going to reinvent the learn SEO wheel here, and instead share a few pointers. 

The bad news is that getting the coveted No. 1 ranking for highly competitive keywords may not happen for a long time (if ever). Wondering why you can’t rank No. 1 for, say, “machine learning tools”?!? The short answer is that many people, companies, research groups, schools, government agencies, and other organizations have published content targeting these same keywords. So what do you do? Here’s your plan:

SEO tips to help your content rank in Google Search

• Get specific

Ranking for broad, obvious, and highly competitive buzzwords related to your market is important. Your marketing website — specifically, your home and about pages — are a good place to incorporate these words. Eventually, you just might make the first search engine results page (SERP) for them.

Focus on identifying the specific (often called “long-tail”) keywords that are part of your USERs’ “lingo” when they talk about their problems that you’re solving.

For example, your product may indeed be a machine learning tool. But what part of machine learning? Do you focus on a particular use case or vertical? Is there another tool or technology that your USERs are currently suffering with that you will replace or augment? These are the words and topics that will surface when you’re interviewing your USERs.

Once you have the list of specific, long-tail keywords that are most relevant to your USERs, put them in a spreadsheet, prioritize them, and add a column named “Content Title” (we’ll use this later).

• Follow technical SEO best practices
Like I said earlier, there’s a wealth of information on technical SEO best practices on the Internet. The TLDR is to write useful headings (H1, H2), titles, and meta descriptions that incorporate your keywords and are relevant to your content. Put yourself in the shoes of your target audience and ask yourself, “What would my USERs search for in Google?” … Then create your content accordingly.

• Get others to link to your content
Getting credible sites and blogs to link to your content will boost your rankings. There’s no real magic here. You just have to ask, beg, and bargain. There are content syndication tools and services that can help, but quality varies. For now, I’d focus on your network and trying to get some well-respected thought leaders in your market to share and link to your content. If the content is useful, people will link to it organically. For technical USER personas, there’s really nothing better than getting your content trending on Hacker News, so figuring out how to do that is a better investment than most content syndication services.

• Monitor your search results
Use tools like SEMRush and Google Search Console to track keyword rankings and to find potential issues negatively impacting your SEO. 

Distributing and promoting content: how to get viewers

You’ve put in the blood, sweat, and tears (hopefully just sweat and a few tears) into your content and hit the publish button. You check Google Analytics and you already have two sessions on your content page! Oh wait, that’s you and your co-founder. OK, so how do you get your actual USERs to find this amazing content that will change their lives forever? While you wait for Google to crawl your pages and your content to make its way to the top of the search results, you can take measures into your own hands.

Social media
Whether or not you have a lot of followers, you must share your content on social media. LinkedIn, Twitter, and Facebook are the obvious big three. Here’s a basic game plan: 

  1. Post on the big three from your corporate account.
  2. Post on the big three from your personal account.
  3. Craft a few posts and tweets for your team, investors, and peers to easily copy/paste on their own social channels.
  4. Continue to do A and B periodically for the weeks and months ahead.


People discover content directly on Medium, so it can be a good source of new readers. However, I am also a big proponent of having a blog that is integrated into your website for brand and SEO considerations.

Website blog + Medium blog or LinkedIn 

The combo approach adds a minor amount of work, but if you want to kill two birds, sometimes you need to throw the same stone twice. Here’s how to syndicate your content:

  1. Post your blog article on your own blog first. 
  2. Wait a day or so and then post the same content on Medium or LinkedIn and always reference that the content was originally published on your blog. 

Boom! You get the SEO on your site plus the reach of Medium or your LinkedIn following. Win-win.

To publish an article in LinkedIn, at the top of your page, click the “Write article” button.

Promote content on your marketing site
This seems obvious, but it often gets overlooked as a promotion opportunity. Create a banner or some type of call-out on your marketing site to promote new content. For example, “NEW! Read our 10 tips for doing things better!”

Email existing leads
If you have any leads in your marketing automation system and those leads haven’t opted out of marketing emails, I say email them! Ideally, you’ll have a library of content and a multi-sequence email nurture campaign or periodic newsletter to share content over weeks and months. But if you don’t have that yet, craft an email for this one piece of content and consider that your first sequence and you can keep adding to it over time.

Influencer or community blogs and newsletters
If you have the right connections or are able to make the right connections, you can try to syndicate your content on key influencer and community blogs and even some “news” sites will let you include your byline. Some may also have newsletters and are typically looking for good content to share with their audience. Always include a link to the content on your site or to your homepage. They may ask you to remove it, but push hard to keep it. Links boost your SEO.

You can always run paid advertising campaigns where the CTA is to consume your content. I don’t usually recommend spending too much on this unless you’re seeing positive ROI. However, a small budget with very targeted campaigns can yield awareness. I favor LinkedIn because you can really fine-tune your audience based on their title, company size, industry, skills, etc. LinkedIn can cost more than other platforms per click, but if you’re getting clicks from your target personas, then it’s typically worth it. 

Placing retargeting ads for site visitors who have not yet consumed your content is also a good option. Google, LinkedIn, Twitter, and Facebook all offer retargeting, and there are options like AdRoll if you’re so inclined.

2. Social media and influencers

We just covered leveraging social media and influencers to distribute content above. But don’t stop there. You should be as active as humanly possible on social media both on your branded corporate accounts and your personal channels. 

In general, use your branded corporate accounts for sharing your company news, marketing site content, and aspects of the company culture. Use your personal social media to engage and share your opinion in relevant conversations. Just keep in mind that, whether you like it or not, you will be representing your brand by way of being a founder and employee. Opinionated and feisty can be a good thing on social media, but just know where to draw the line.

As for influencers, the goal here is to build relationships with key influencers in your market. If you don’t know them, reach out to them and let them know you’ve started a company and want to get their feedback. If all goes well, they will follow you on social media and share your posts and/or mention you in relevant conversations with your USERs.

The goal in all of this is to gain awareness with your USERs by sharing content, participating in relevant discussions, and ultimately getting others to help you spread the word. 

3. Specialized communities

If your USERs participate in specific communities or meetups, you should get involved. These are often vendor-agnostic, so approach these groups with care. You don’t want to come in with your sales guns blazing and pitching your company every chance you get. If you’re new to the community, ease your way in and get to know the culture and norms. Your goal is to become a valued member of the community and through that, you’ll ultimately build awareness (and goodwill) with members. Hosting or buying food and drink for community events is always appreciated. You’ll get an opportunity to present or share more about your company down the road, but you’ll be better off in the long run if you earn that right over time versus pushing to get on stage right away.

4. In-person events

Trade shows, industry conferences, and meetups are great ways to introduce your company and your product to USERs. Just be selective in the events you choose to attend and sponsor. Large events can be expensive just to get a ticket, not to mention securing a booth in an exhibit hall or sponsoring the WiFi. And it’s easy to get lost in the crowd at these big shows. 

In the early stages of your business, I recommend smaller, niche, highly credible events that give you the opportunity to engage with USERs. Community meetups are great if you can find ones with the right audience. You should apply to speak at big and small events. Generally, event organizers don’t accept abstracts that are company or product pitches, so offer to present something tangentially related to your company and product. For example, if your product serves developers, suggest a technical talk about your architecture. 

5. News and podcasts

PR will certainly help build awareness, but the challenge is getting coverage in the right outlets. 

PR agencies aren’t cheap and typically require long-term commitments. In the early stage of your company, you probably won’t have an ongoing need for an agency, so the ROI is just not there. With that said, there are consultants and some agencies that will work with you on a per-project basis — for example, coverage for a company launch and funding announcement. 

Podcasts can be another way to get in front of your audience and many podcast hosts are always on the hunt for their next great interview. Find the right podcast and see what it takes to get interviewed. Like speaking at a conference, you may be asked to speak about topics other than your product. 

How to create content that’s actually valuable to your USERs

Yes, your content must include the keywords you’re trying to rank for in Google Search. But, keyword soup (a relatively useless page that just uses the keyword dozens of times) won’t do the trick. The content must be useful to your USERs. Useful content depends on your USERs and their problems. 

What is useful content?

Let’s use an example to illustrate useful content. Let’s say our USERs are developers. We offer an observability and performance monitoring tool, and we know from our USER interviews that fixing poor-performing SQL code is a major challenge for our USERs. Useful, awareness-level content will provide actionable, code-level, copy/paste details for tuning a variety of SQL statements. It’s critical that this content not be grounded in your product or about how your product solves this problem 10x faster, better, or cheaper. It is simply helping a USER solve a problem. By doing this, USERs become aware of you and because your content was valuable, they will come back for more. And we will guide them to your product education material when the time is right.

People can sniff out good content from the search result listings. The more people who click on your links in search results, the higher it will rank. The more that people share and link to your content (because they found it useful), the higher it will rank. And don’t lose sight of the fact that we are doing all of this to gain awareness and educate our target USERs in service of converting them into happy, paying customers. If the content isn’t useful, they will likely continue their journey without you.

Now, go back to your spreadsheet from step 1 and add a title (you can change this later) for the content you will create for each of your keywords in the “Content Title” column. In an ideal world, the content would be part of an interconnected sequential story, perhaps with chapters, but that isn’t always possible and in the early stage of your business, isn’t necessary. Our goal is to get this useful, high-quality content published ASAP so we can get the SEO goodness started.

Creating really useful content: 3 things to consider

When USERs are looking for solutions to their problems, they’re looking for information. Two primary ways people obtain information are consuming content and talking to peers. We’ve already emphasized the need for your content to be useful to your USERs, so I won’t belabor that point any more here. We also started a spreadsheet with our most important keywords for SEO and added titles for content we need to create related to those keywords. Now comes the execution part — creating all of that content. Here are some considerations and a few recommendations to help you get your creative juices flowing.

Get creative with different formats of content
When many people hear “content,” they think “blog article” or another form of writing. This is logical, especially since writing blog articles can be one of the easiest, fastest, cheapest, and most agile ways to create content. However, I highly recommend that you not get too addicted to the blog. Creating a dedicated education portal with content in a variety of mediums — especially videos and podcasts — is really valuable. For audio and video, you can write a blog article or create a landing page to describe the content and even post the transcript to get more SEO benefit.

• Experiment with content length
Some people only consume bite-sized pieces and others prefer longer, more thorough content. You’ll be able to track which content performs better and learn what works best for your audience. I frequently create a long-form content piece and then cut it up into smaller pieces to share on social media, in newsletters, etc.

• Run webinars
Whether you call them “virtual office hours” or “weekly demos,” the webinar format works well for both traditional, lecture-style webinars and more informal virtual meetups or product demos. People expect to register for webinars, so it’s not an issue to require at least an email. 

You can get interesting metrics about engagement during the webinar as well, which can help with your post-webinar followup strategy. The icing on the cake is that you can make the webinar recording available on your site, YouTube, or another video platform. You can also cut the recording into shorter segments and distribute them as teasers on social media and throughout your website. 

To gate or not to gate content

Should you gate your or let anyone and everyone have access to it? I’ll answer with the always helpful “it depends.” In case you’re not familiar with the concept, gating content just means that you require consumers to provide their contact information in order to access the content piece. Basically, they need to fill out a form before they get the information they want. 

Whether or not to gate is all about trade-offs. But before I discuss the main trade-offs, let me first mention retargeting (see Leads! How do we get more leads?). If you’re running retargeting advertising campaigns or at least building retargeting audiences for future use (which I recommend), you can advertise exclusively to anonymous content consumers with offers that entice them to progress to the next funnel stage, such as more educational content, an upcoming webinar, or and enticing offer such as “extended free trial.” How well those programs work for you will be a factor when deciding whether or not to gate content. 

What are the main trade-offs in deciding whether to gate content?

  1. SEO may not be as impactful with gated content
    It is possible to get gated content indexed and crawled by search engines, but it’s not ideal. If SEO is your main objective, you probably don’t want to gate your content. If you still want to gate, you’ll have to invest some time and resources into implementing a gating system that still supports being crawled by Google. You can also implement a mix of gated and ungated content, such as ungated for blog posts and gated for special types of content, such as ebooks that require a user’s contact information.

  1. Volume may be smaller with gated content

Keep in mind that unless you’re The New York Times, if you gate your content, fewer people will consume it. It’s just a fact of life. Some people will not part with their email address to gain access to content, and therefore the number of people digesting your content will be lower. If getting this content out to the masses is your main objective, then I wouldn’t gate it. 

  1. Leads and lead readiness may not be as high with gated content
    The health of your marketing funnel may help you decide. If you don’t have any other way to get leads or if you are looking to rev up the top of the funnel to get more leads, you may be inclined to gate. In my experience, consumers who come to your site through gated content are rarely ready (or receptive) to having a meaningful sales conversation. If getting SQLs is your main goal, I suggest experimenting with gating content that appeals to USERs who are at or approaching your education GTM funnel stage. If the experiment doesn’t yield the results you’re looking for, you can always remove the gate.

  1. Readiness to nurture may stall with gated content
    Leads go stale. In fact, they go stale quickly. The good news is that with proper nurturing, you can preserve the longevity of your leads and get them ready for the next funnel stage. When deciding on gating, consider whether you have the means to properly nurture your not-yet-sales-qualified leads. At a minimum, you’ll need more content and a sequence of automated emails sharing this additional content over the course of weeks, months, and forever.

So, should you gate or not? Without more information, my answer is no, you should not gate. The goal of content is to build awareness, and the conversion is the USER moving into education. Have faith in the Modern GTM process and your ability to execute further down the funnel. Use awareness content to maximize your SEO impact and get the good word out. You’ll have ample opportunity to convert your aware USERs into leads, opportunities, and customers once they are ready.

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