How Headline Invests In Content For Early-Stage Companies

Taylor Brandt is an early-stage investor at Headline, the multistage venture firm helping teams win on a global scale. Headline closed another billion dollars on their early-stage funds in North America, Asia, and Europe and is increasing fund size and check deployment.

Recently, Taylor has focused on companies building vertical software, B2B marketplaces, commerce enablement and go-to-market technology. We sat down with her to discuss a variety of topics, including:

  1. Why early-stage companies should invest in editorial
  2. How to combine strong messaging and social proof 
  3. The outsized value of creating content flywheels
“For early-stage companies looking for the best multipurpose sales and marketing investment, content is the answer.”

Why VC-Backed Companies Should Invest in Content

Taylor shares the investor's perspective on how companies should think about content:

  • The correct point in the company life cycle to turn on content
  • How content can boost a go-to-market push
  • What it means to invest in content

For Taylor, it’s time to think about content only after you've figured out your customer and ICP, and you've done some solid, initial product testing.

The intention is that you've already gone through betas where customers expressed that they liked the product, and you’ve refined the value prop of what you're selling.

After that, content is a great way to jump-start scaling an honest go-to-market effort.

Content-Assisted Growth Motions

Over the last few years, there's been a lot of hype over product-led growth motions. In reality, Taylor sees most of the companies she works with as having some form of a sales assist model.

Generally, these companies have some amount of traffic that comes in through content, SEO, and demand gen, part of which is self-served through a PLG motion.

Sales assist bolsters some of these motions, and some of that is just top-down for startups targeting larger companies.

Regardless, Taylor stresses that content will continue to drive awareness and provide value throughout the buyer journey, often serving as a vital asset for PLG or sales assist.

When to Invest in a Flywheel

Once you have established value prop messaging, you can talk to potential customers and start building pillar content and SEO to jumpstart that inbound flywheel.

Taylor stresses that the sooner you do it, the better, as the investment of time and resources will only compound over time as the flywheel picks up speed and content drives outcomes.

She notes that it’s only worth investing in content once you’ve ID’d the problem you're solving.

Taylor suggests that a natural way to make content investments is to plan around fundraising rounds – this can either preempt and support a raise or leverage new capital from a raise.

We’ve seen that most companies come to Verbatim after raising a seed or series A, and usually, they raised those rounds because they had a good idea of who their customer is.

From her vantage point, Taylor sees that companies should turn on content after early signs of product market fit. Depending on company size and vertical, you need more or less time to discover it.

Typically, Taylor sees startups turn on content roughly six months after a seed round as part of the preparation for raising an A round.

“Don't front-load the work before you actually know what your business is doing and who you're solving the problem for.”

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How to Make the Most of Your Content Investment

For companies in the seed to series A stage, bang for your buck, communicating value across channels, consistency, and messaging all matter.

Through conversing with founders who don't have content or even marketing backgrounds, we constantly find ourselves explaining the multiple use cases for content.

Taylor highlights that a content function isn’t just posting the blog and pushing it on social media. Content isn’t a stand-alone lever, it’s the fuel for all marketing and sales efforts:

  • Your sales and partnership teams should both be using the content. 
  • It should be in email campaigns and drip sequences. 
  • It should be incorporated on specific landing pages.
  • You should be backing it with paid campaigns. 

Taylor points to a company like Gong. Is Gong by far the best product? Probably not.

Was Gong exceptional in widespread branding, messaging, and content and being immediately associated with the concept of sales coaching and transcription? Absolutely.

She stresses that the more you can push the same message and build brand affinity across multiple touchpoints, the more you will resonate with potential customers.

On average, consumer businesses take seven touches to get a conversion; that number is higher in B2B. The more your message resonates, the better.

Create Repeatable Content Flywheels

Taylor has a few tips for optimizing your cash during the early days of GTM efforts:

  1. Use unpaid channels to validate paid channels. Don't blow a bunch of money pushing it through paid channels unless it worked on unpaid.
  2. If you have high open rates, click-throughs, and engagement on unpaid channels, push that out as far as possible to reel people in.
  3. Create mechanisms for repeatability of the most effective methods.
  4. Repurpose content across touchpoints. This is not only cost-effective, it fosters familiarity and resonates with buyers.
“Content is a great mechanism that doesn’t just drive its own impact but also supports and helps stress test other functions.”

Using Content to Streamline Marketing Touchpoints

Every company wants to find the best shortcut for its sales cycle. Reducing the touchpoints needed to close a customer saves money and maximizes the success rate.

Taylor has seen the most successful B2B companies leverage certain tactics to speed up the sales cycle, including:

  1. Engrained social proof in content to reach customers from a foundation of credibility
  2. Comparisons to help customers differentiate between available options

The best companies use comparisons to simultaneously lay out their value prop, why it's different, and how other products on the market are the best fit for different types of customers.

This not only helps find the right customer early on, but it also allows people to believe that the company is invested in more than the customer dollar.

Taylor stresses that having balanced content that understands the customer and how they make choices matters.

Leverage Social Proof To Establish Expertise

From a customer standpoint, case studies and proof points are exceptionally important. They build an understanding of what verticals a product applies to and how customers can implement and get utility from it.

Every customer has to understand, “does this product work for my particular use case?”

So when people search for products and solutions, the right case study can seriously boost the applicability of the product. 

When you think about sales, marketing, demand gen, and content for vertical-specific categories, there are typically experts in that vertical or industry with big followings.

By featuring high-profile people, you effectively get a free introduction to their audience.

For example, if you see content with Kyle Parrish today, you immediately associate it with sales – Kyle has created a successful brand in sales. If you're looking at tools to boost sales, you likely want to know about his tech stack.

Aligning your tool or product with industry leaders is an incredible way to get a brand halo and social proofing since people naturally want to mimic those succeeding in the space.

“Most of the time, people just want to see how they can incorporate what other people are already doing – especially someone that is having success.”

Lightweight Tactics For Early-Stage Companies to Test Content

What’s the best way to know if content will drive real impact? Find easy ways to produce a few pieces and learn as much as possible before doubling down.

For teams looking to test content before committing and investing, Taylor suggests running a batch of initial case studies to generate learnings.

Using that content in as many ways as possible can validate content as a worthy investment.

If the case studies and the content you create to repurpose them drive real impact (which they almost always do), then companies know that they should spend more time on it.

“Hire a freelancer or studio to write five articles or have your sales team do two case studies. See what happens and keep recycling it to get the initial learnings.”
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