How to Take Your Content Upmarket When You Take Your SaaS Business Upmarket

Nearly all SaaS businesses aspire to move upmarket.

Moving upmarket means acquiring larger customers who spend more money. There’s a financial incentive to move upmarket … you can make more money with fewer customers. The revenue is also more stable because large companies tend to change SaaS tools less frequently.

This is also how innovators disrupt. We’ve all heard the story of upstart steel manufacturers producing low-end steel in mini-mills, then slowly eating up the market that had so long been dominated by the integrated steel companies. (And if you haven’t, it’s time you read Clayton Christensen’s The Innovator’s Dilemma.)

The desire to move upmarket is hard-coded in the DNA of most SaaS companies. The pay-as-you-go model combined with the efficiency of software means that cost- and time-savings can eat away at all kinds of other businesses. It's only natural that these companies want to inch their way towards the bigger pockets of enterprise companies.

The transition from selling to SMBs to the enterprise is a gradual one. It's not one that happens overnight and it tends to bring all kinds of unforeseen friction. It's worth considering whether you truly want to move upmarket—i.e., hire an outside sales team, bring on account execs, optimize the product for the enterprise, etc.—or if you'd just like to close some bigger deals with lower churn risk. There is overlap in the strategies, but these are distinctly different business models.

Still, if moving upmarket is part of your plans, you will need to adjust your content strategy accordingly. We have plenty of advice on the topic, but let this post serve as a reality check as well. Is moving upmarket really the right move for the business? Assuming you're ready to proceed, here's how you'll need to rework your content strategy.

Expand Your Footprint

In the early-stage companies, content creation is limited by available resources. There is a small marketing budget, therefore founders and early employees take on the responsibility of writing blog posts and ebooks themselves. This constraint is a good filter on quality. There's no time to write blog posts that aren't worth writing. It's easy to keep quality high when you only write when you feel you have something interesting to say.

Scaling content is hard whether you're trying to move upmarket or not, but you'll almost certainly need to create more content if you're planning to target large companies. This happens for a few reasons:

All of this changes when you're targeting larger customers. You'll need content that addresses your new personas from the top of the bottom of the funnel. You'll also need to rethink your SEO strategy since you may need to start competing for different keywords. You may even need to supplement with paid search to figure out what kind of content resonates with your new audience.

It's really easy to let quality slip as you scale. Don't assume it will be easy, and don't hesitate to rein in quantity until you've got good processes in place to ensure quality. Here are a few suggestions to make that happen faster and more easily:

  • Put an experienced content person in charge. Hire someone who knows how to run a content marketing operation, then let them decide if you should hire content creators in-house, find contractors, or partner with an agency. Scaling is easier when (1) a dedicated content marketer or editor runs the show and (2) that person can come up with the vision and execute it.
  • Break content into tracks with their own cadences. It might look something like this: one benchmark report per year, one whitepaper per quarter, one ebook per month, two blog posts per week. You'll need to start planning your editorial calendar months in advance to assign out the work, so use tracks like this to plan and budget content. It also decreases project management, which becomes a challenge when teams start publishing more often.
  • Don't overspend on content creation. If you don’t spend enough on content, you’ll never get the quality needed to stand out. If you spend too much, you’ll create overhead for your team and quality will actually decline. Keep your operation lean with a strict emphasis on quality and results.

Content marketing often works because it engenders trust and goodwill with readers. That's lost if you publish low-quality content. If you've built a brand with content, don't turn all of your attention to distribution and pageviews—keep the authenticity of the content intact.

Address the Bottom of the Funnel

Enterprise sales cycles are measured in months, not weeks. The larger the deal, the longer it takes to close. Here are some rough estimates courtesy of Jason Lemkin:

  1. Deals < $2,000 in ACV (annual contract value) should close on average within 14 days.
  2. Deals < $5,000 in ACV should close on average within 30 days.
  3. Deals < $25,000 in ACV should close on average within 90 days.
  4. Deals < $100,000 in ACV should close on average within 90-180 days depending on # of stakeholders and gates.
  5. Deals > $100,000 in ACV will take on average 3-6 months to close. Of course, some faster, some shorter.

When you're selling to SMBs, a great product and self-serve sales process work well—and quickly. As the sales cycle expands, content can fill gaps between meetings and emails. Content that addresses the bottom of the funnel is exceedingly useful in long sales cycles.

Content for the bottom of the funnel is optimized for purchases, not search engines, email or any other channel. It's created for prospects that have passed the “awareness” phase and have moved onto interest, desire and action.

Here are just a few bottom of funnel content types that can work well in a long sales cycle:

  • Case studies: By the time a prospect is interested in your product, they will also want to see how it's worked for others.
  • Webinars: Popular in sales-focused organizations, webinars can be semi-automated to work over and over again.
  • Industry/benchmark reports: In addition to driving top of funnel awareness, reports can be used as sales collateral during long sales cycles.
  • Whitepapers and ebooks: Premium, gated assets are a great way to engage prospects that are considering where, how and why to deploy your software.
  • Product updates: Have you taken measures to improve security, boost uptime or better the product? Don't be shy about writing about it.

If you're having trouble coming up with ideas for bottom of funnel content, talk with your sales teams. They need (1) reasons to reach out to prospects during the sales process (“Have you seen the industry report we just released?”) and (2) good fodder for discussion topics during meetings (“Another customer increased productivity by 15%, I'll send you the case study.”)

In our experience, bottom of the funnel content is sorely underutilized. It can be used to move prospects from the top of the funnel to middle, and can also be used to upsell customers months or even years after they come onboard. It won't rack up tons of pageviews and it may be difficult to directly attribute sales to it, but your sales team will be able to tell you whether or not it's working.

As a general rule, have at least one piece of content for each week in the sales cycle. That doesn't mean you have to send it, but you should have it available.

Deal Size (ACV)Length of Sales CycleBoF Content Pieces
<$,200014 days2 to 4
<$5,00030 days4 to 8
<$25,00090 days12 to 20
<$100,00090-180 days25-40
>$100,0003-6 months50+

As we often say, make sure you have a way to measure content in a way that aligns with the value it provides. These articles, PDFs, and videos are very unlikely to rack up pageviews, so put another mechanism in place to monitor conversions and check in with your sales team to find out how useful each piece is.

Keep It Genuine

There are a number of small start-ups that have earned a great reputation for excellent content. There are very few large companies that regularly produce good content. Why is that?

Smaller companies, often due to budgetary constraints, look to their founding team and early employees to create content. These people have something to say. Instead of targeting keywords and worrying about pageview growth, they write essays, thought leadership pieces and share their personal experiences growing the company. We call this movement-first content. The primary goal of movement-first content is to inspire, not necessarily to inform.

As content operations scale, it's very easy to let movement-first content fade into the background. After all, there are metrics to track, keyword opportunities to tackle, and distribution channels to capitalize on.

We encourage you not to let this happen. Content with a personal touch will stand out even more as you move upmarket. The increased focused on data means there are fewer genuine, interesting thought leadership posts floating around the enterprise space. It's a consumer-grade style of content that resonates with all buyers, regardless of the size of their company.

It's difficult to pinpoint exactly where movement-first fits into a content strategy. Is it meant for the top of the funnel or the bottom? Will anyone sign up for a free trial after reading it? Should we try to optimize the posts for search? You may very well have to answer those questions in order to move forward. It's worth it. The best content builds trust and galvanizes readers. Allow time and space in your strategy for writers to get creative and for readers to be inspired.