Optimist is a full-service SaaS content marketing agency and this case study is based on the content marketing strategy we executed with HelloSign’s team from 2017 to 2021.

It was a frigid cold day in Des Moines on January 28, 2019. 

Like most January days, I was just hoping to hold on a few more weeks until the early signs of Spring would start to thaw things out and give me that yearly boost of energy.

But, it turned out that I was going to get a different kind of jolt.

Dropbox Acquires HelloSign for $230mm,” the headline read in my push notifications.

I stared at it for a long time.

A combination of shock and elation took hold as I bounded out of bed.

HelloSign and Optimist had been working together for nearly two years at this point. But I had no idea that the acquisition was in play. The whole deal has been basically kept under wraps. Most of the team only found out about it right before it was finalized.

It was a momentous achievement for the HelloSign team—and I felt lucky to have been along for even a small part of the ride as their content marketing partner.

HelloSign's Organic Traffic Growth (October 2017 to January 2019)

Over the preceding 17 months, Optimist worked closely with the HelloSign team to create and execute a strategic SaaS content marketing plan. During that time, we saw their organic traffic grow by 1,308%. This correlated almost perfectly with their business growth and subsequent acquisition.

This article is about our journey with HelloSign and what we learned about SaaS content marketing along the way.

From Series B to Acquisition: The Two-Year SaaS Content Marketing Journey

When our team first started working with HelloSign in 2017, they had just raised their $16MM Series B round. They were on a path to rapidly expand their eSignature solution, roll out HelloWorks, and move upmarket with HelloSign integrations and API.

There was a ton of content and strategy to figure out.

Luckily, both our team and the HelloSign team are full of outrageously smart people. We dug in and created a SaaS content marketing strategy that could support their very ambitious goals.

Throughout this process—and in working with many other SaaS companies over the years—we developed and refined some key strategies and tactics that we use to drive growth for all our clients. 

In particular, we learned a ton about how content marketing for SaaS can provide value to prospects at every stage of the funnel, drive site traffic, and, ultimately, increase conversions.

SaaS Content Marketing Goals

One of the founding principles behind Optimist and our work with clients is that not all content is the same.

Different types of content can support different types of goals. And, that content should work together to drive the overall business goals. So, as with any ambitious undertaking, the best SaaS content marketing starts from a place of intention. 

Before you can put a plan into action, you need to understand the desired outcome. That means pausing to ask, “What’s the goal of our content marketing work?”

For most SaaS companies, common goals for their content marketing involve driving product signup, trials, and website traffic

But that’s not always the case. 

Depending on your current growth trajectory, PMF, and product stage, there are plenty of other goals that can factor into your success. For example, some other SaaS content marketing goals that might be on your radar include:

  • Building brand awareness
  • Creating a pre-launch waitlist
  • Generating leads
  • Attracting a new market segment
  • Growing your email list
  • Upselling to larger plans
  • Improving retention
  • Increasing customer lifetime value

Of course, your goals might shift along with market changes, customer feedback, new releases, and your company’s growth. If you’re feeling stuck and aren’t sure what your content marketing goals should be, there are a few things to consider. 

1. Define the current state of your product

This is one of the biggest factors when it comes to informing your SaaS content marketing goals—and it’s pretty straightforward. Is your SaaS product pre-launch (e.g., in development or beta), recently launched (e.g., pre-traction or initial growth), or established within the market with clear product-market fit?

SaaS startups in the pre-launch phase—whether their product is still in development or beta testing—will have very different content marketing goals than businesses with a live product and growing customer base. 

2. Decide where you want your business to be six months from now

Look at where your SaaS product is now and compare it to where you want it to be in the next six months. 

Content marketing is not an overnight venture. So, you shouldn’t be setting plans for next week when thinking about the goals for your content marketing strategy.

Ask yourself a simple question: What would success look like 6 months from now?

Do you want to increase revenue from existing accounts, bump up your trial conversion rate, or tap into new lead sources? The more specific you can get, the better.

Ideally, pin a specific sales, lead generation, or revenue KPI to your content marketing.

3. Identify what needs to happen for you to get there.

The magic happens when you recognize what levers need to be pulled in order to move from where you are now to achieving your growth goal.

  • If you’re early stage in your growth and not seeing much traffic, then you’ll want to begin by building an SEO strategy and identifying the high-value keywords that will attract your target buyers
  • If you’re seeing a decent amount of website traffic but struggling to convert, you’ll likely want content that demonstrates product value and helps convert blog readers into SaaS leads
  • If your goal is to grow your email list so you can nurture prospects with a sales workflow—in which case a combination of mid-funnel blog content + qualifying lead magnets might be just what you need

When we began working with HelloSign, their goal was simple: Scale inbound signups and trial activations. Here’s how we used content marketing to help them achieve this.

Using SaaS Content Marketing to Drive User Signups

Although there are many potential content marketing goals that could be appropriate for a SaaS company, the vast majority have pretty straightforward needs:

  1. Increase qualified traffic
  2. Drive product sign-ups and trials
  3. Everything else. (Brand awareness, leads, emails, etc)

HelloSign is no different. 

Although there were a number of market forces and products in play, the ultimate business objective of our work with HelloSign was to increase user signups.

So, that’s what we set out to do. 

The question was, how could we use SaaS content marketing as a lever for capturing the right audience, communicating product value, and ultimately converting prospects into customers?

In most instances, these goals feel at odds with one another. 

The content that is most valuable to you as a business (most product-focused) is often less valuable to a reader who is trying to learn about a topic or solve a problem broadly.

So, how can you strike a balance between providing value to your audience and value to your business?

The key is to unpack the various moving parts and create a SaaS content marketing strategy that addresses each specific goal and also solves for the overarching business objectives. 

In other words, break it down and solve for each piece independently. Then pull everything together into a cohesive SaaS content marketing plan.

The SaaS Content Marketing Paradox

Very few prospects jump from reading top-of-the-funnel content to immediately signing up for a product. Instead, most SaaS product signups (trials, leads, etc.) come from the middle of the funnel.

In other words, a prospect who’s ready to convert has already researched their problem, discovered a general solution, and started searching for products that offer it.

For SaaS content marketing to be successful, you need to put a lot of emphasis on driving solution-aware traffic to both content and product marketing pages that are in the middle of the funnel.

But there’s a challenge

The pages on your site that are most relevant to a middle-of-the-funnel buyer are your core product pages—features, integrations, solutions, etc. 

These are notoriously difficult pages to rank (especially in a crowded market like eSignatures) because there are very few ways to naturally accrue links or promote such product-focused content directly to a prospect. 

HelloSign's Product Marketing site is full of targeted landing pages

This creates a paradox.

The pages you care most about ranking and generating traffic to are also the most difficult to rank and drive traffic to. 

So, how do you overcome this obstacle, resolve the paradox, and restore order to the universe? (Okay, maybe just that first part.)



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    The solution is to create a framework that leverages top of the funnel content to generate not just traffic, but also links (domain and topical authority) that help these important pages rank over time.

    This has become the basis of our approach to SaaS content marketing for our clients.

    How Optimist Approaches SaaS Content Marketing

    Before we get into the specifics of how we executed this strategy, I want to reveal the framework that we use to shape our thinking and our approach. 

    This framework builds on our trifecta strategy that we originally developed from my work scaling College Raptor from 0 to 100,000 organic searches/mo

    But, given the specific nuances of the SaaS business model and the extended B2B buyer’s journey, it’s not a simple cut-and-paste process. 

    The framework that we developed integrates key insights about how buyers interact with SaaS businesses and which strategies are most effective for driving actual conversions.

    For our work with HelloSign, we applied a framework similar to this. Ultimately, we’ve found that most SaaS businesses have similar goals and thus, the overall approach to content marketing is a variation of this general framework. 

    It’s not one-size-fits-all, but it’s about as close as you can get when you’re talking about true strategy.

    SaaS Content Research and The Importance of Knowing Your Customers

    Before we could tailor this framework to support HelloSign’s specific growth goals, we need to get a clear view of their ideal buyer. That meant learning everything we could about their customers’ pain points, needs, and influences on their buying decision.

    We then used this customer knowledge to inform everything from our keyword clusters, editorial calendars, and promotion plans.

    How well do you know your customers? 

    In addition to researching market trends and tracking how users interact with your product, it’s worthwhile to ask customers for input directly.

    How did they first discover your product? What made them choose you over competitors? Why did they select their current plan? 

    When it comes to creating content that speaks to your audience, knowing your customers—who they are, what challenges are they facing, and what motivates them—is crucial. 

    Here’s why it matters. Approaching SaaS content marketing through the lens of the customer allows you to:

    • Consistently create relevant content. When you know exactly who your leads are and what they’re searching for, you can create content that speaks directly to them. 
    • Provide more value. The better you understand your prospects’ pain points, the better you can help solve them through content. 
    • Increase web traffic and time on site. Content based on a combination of customer feedback and keyword research is more likely to get leads attention, convince them to click, and keep them on your website for longer.
    • Generate content ideas without getting stuck. Customer pain points can be a powerful source of inspiration for new content ideas and topics. 
    • Drive action and conversions. Find out what made existing customers convert and look for ways to recreate that same “aha” moment for new leads. 

    By taking the time to understand HelloSign’s ideal customer base, we were able to devise a strategic content marketing plan that catered to prospects at every stage of the funnel. 

    The SaaS Content Marketing Funnel: A Top-Down View

    The SaaS content marketing funnel can be broken down into four main sections. Content played a key role at each of these stages in helping HelloSign attract, qualify, persuade, and convert traffic into users and users into customers. 

    But before we dig into the specifics of how we used content at each stage of the funnel to promote HelloSign’s goals, here’s a quick overview of the stages themselves. 

    1. Pre-funnel content 
    2. Top of the funnel content
    3. Mid-funnel content
    4. Bottom-of-the-funnel content

    Pre-funnel content is used to attract potential leads who aren’t necessarily shopping for a solution—yet. This content appeals to anyone who fits the ideal buyer persona and provides solutions and insights that don’t necessarily tie into the product itself. 

    Leads who really click with this type of content might explore the site further, perhaps by way of in-text links that move them into more top of the funnel content.

    Top of the funnel content is written for leads who are problem-aware and beginning to research solutions. This could be anyone who is actively searching how to deal with a pain point—but is still a long way from making a purchase. 

    Content geared for this audience is typically evergreen, educational, and problem-oriented. It often highlights the benefits of the SaaS product and positions it as a possible solution to the prospect’s problem. 

    Mid-funnel content is even more directly linked to the SaaS product. This includes features pages, case studies, and other product-related content like implementation guides and walkthroughs. 

    At this stage, the goal is to educate and persuade readers on the benefits and outcomes of using this product in particular.

    Bottom of the funnel content can lean into more product-heavy sales pitches that position the SaaS product as the ultimate solution.

    Leads interested in bottom-funnel content are primed to make a purchase and are looking for information and proof that either supports or changes their opinion. They might be comparing a few different brands with the intention of signing up for a trial or paid account.

    Now let’s take a more detailed look at the various types of content that were part of HelloSign’s massive growth.

    Pre-Funnel SaaS Content: Targeting the Right Buyers

    Before we dive into the actual funnel and the buyer’s journey, I want to begin with what we call pre-funnel or persona-qualified content. 

    Although it’s often at least one step removed from a buying cycle, pre-funnel content can serve an important supporting role in a SaaS content marketing strategy. The idea here is to create content that attracts your target buyer broadly, even if they aren’t problem-aware.

    Thought leadership content attracts relevant buyers, even if they are pre-funnel.

    Case in point: HelloSign speaks a lot to sales leaders in their content. We created a lot of content that was aimed at generally helping this persona do their job better, even if that didn’t involve using HelloSign’s products to do it.

    This allows us to accomplish a number of things: 

    1. Expand search/social footprint
    2. Build brand awareness and familiarity with our target personas
    3. Drive retargeting and email marketing

    Pre-funnel content can be valuable in the right context, but it can also be a distraction from the key objective. It rarely translates into immediate conversions. 

    So, don’t let it become the center of your approach unless you have already built out every other part of the funnel in full.

    Top of the Funnel SaaS Content: Helping Prospects Solve Problems

    In the world of content marketing—especially SaaS content marketing—the top of the funnel is often misunderstood.

    Our take is simple: The top of the funnel starts when a buyer begins to actively learn about or seek a solution to problem that could lead to a purchase.

    In our work with HelloSign, we considered a user to have entered the funnel whenever they began trying to resolve a pain point that could potentially result in a conversion.

    So, for instance, if the buyer is a VP of Sales or Sales Operations Director, then they might begin their journey by looking for ways to accelerate their sales cycle—to cut down the days between contact and close. 

    One solution to this problem is to implement eSignatures.

    From a content perspective, we target this initial need as an opportunity to capture the buyer at the point where they are looking for solutions to a problem. In my post about SaaS SEO, I talked about our process of using a JTBD framework to identify and map these specific pain points to key product use cases and features. 

    Within the top of the funnel content, we break down our content strategy into 3 key types of content that each serve a specific purpose. I’ve outlined this approach before, but it allows us to get very specific and tactical while staying strategic in our content planning and creation. 

    1. Social-viral content (Thought leadership)

    For HelloSign, what we pursue as social-viral content is strong thought leadership content that’s likely to generate a lot of shares and buzz around a particular topic. 

    W found is that the more of a strong stance we are willing to take topics related to work, culture, and operations, the more reaction we generate among our target readers. Of course, this approach can be polarizing as well.

    The key to our approach here is to be thoughtful about where we plant a flag.

    Knowing that readers who align with specific thinking are most likely to become users and customers, we can draw a line in the sand to help attract like-minded buyers who feel strongly about the nature of work and productivity. 

    Social-viral style content aimed at agitating common problems and generating product demand for HelloSign's eSignature software

    Keep in mind that the search (SEO) opportunity for this content may not be enormous.

    That’s okay. 

    The role of this type of content is to reach prospects through channels other than search: social and community channels. The goal is to generate buzz and demand based on the content and drive problem awareness. 

    The downside is that these topics often have a short shelf life.

    They’re perennial rather than evergreen. We can circle back to them every few months or every year and use them to drive traffic through key channels.

    2. Evergreen SEO content

    The meat and potatoes of effective SaaS content marketing–the workhorse–is evergreen content.

    Evergreen content targeted prospective buyers based on need at the top of the funnel

    This topical, keyword-focused content ranks for the most relevant keywords our persona is searching at the point where they begin a buying journey. The beautiful thing about evergreen content is that it’s–well–evergreen.

    It may not generate a giant spike in short-term traffic or go viral and spark a massive debate, but it brings in consistent, predictable, scalable, and targeted traffic every single week (almost) like clockwork.

    Analytics show evergreen traffic growth as it compounds over time.

    Best of all, if you’re doing it right, that traffic gradually increases over time. And combined with the creation of new evergreen content, you’re able to generate a compounding effect that accelerates growth in the long term.

    Building a strong library of evergreen content is the bedrock of high-growth content marketing for SaaS businesses.

    But it doesn’t work alone. You also need links.

    3. Linkbuilding content

    Let me preface by saying that linkbuilding for HelloSign was a relatively light process. Because they already had an established brand and had generated a lot of PR, their site already had a pretty strong domain and topical authority when we began working together.

    Trends and other information leadership pieces were used to build targeted links to help drive SEO across the HelloSign website.

    But, regardless of existing domain authority, building links is an essential part of any SaaS content marketing plan. 

    Growing links to your site is critical to help your content (and pages) rank for the terms that are most important to your business. Many studies have shown not just the correlation between links and rankings, but that without building links to your site and your content, you are doomed from a rankings perspective

    Now, if we look back at our framework, we can start to see how we use these different types of content to drive growth by working together.

    And that’s just the top of the funnel.

    But, we’ve just begun. Next up, we’ll get into more product-focused content and pages in the middle of the funnel. Remember, this is critical for growing targeted, high-intent traffic from prospective buyers.

    Middle of the Funnel SaaS Content: Driving Traffic to Product Marketing Pages

    Prospects who land on content and pages in the middle of the funnel are typically solution-aware. They’re actively looking for information about a certain product category or key product features.

    This is what makes these pages so valuable for a SaaS business. 

    Compared to top-of-the-funnel traffic, these prospects understand the problem they are looking to solve, they have higher product/purchase intent, and most importantly they’re closer to making a purchase decision.

    Rather than helping prospects understand their problem or pain point and then introducing a solution (generating demand), the middle of the funnel is the opposite. There is existing demand for the SaaS product and our job is to get in front of those people who are looking for a solution.

    So how do we create content that captures this demand?

    There are two main types of content that we tend to focus on: Product marketing pages and case studies.

    But this is not exhaustive. Many types of content and keywords will fall into the middle of the funnel if they signal some level of purchase intent. That context will depend heavily on the SaaS business, the target buyer, the vertical or industry, and the overall buying cycle.

    For instance, someone looking for something as broad as “sales tools” could be considered in the middle stages of their buying journey in the right context.

    But let’s get back to HelloSign.

    These are the two types of middle of the funnel content that made up most of our work in this case.

    1. Product Marketing Pages

    The bread and butter of the middle of the funnel are product pages like:

    • Features
    • Integrations
    • Solutions

    In HelloSign’s case, this content existed on the marketing site.

    HelloSign's marketing site houses a number of specific and targeted product marketing pages.

    They had a healthy catalog of specific product pages, including all of the features, use cases, and persona-driven content that was well-suited to rank for middle of the funnel keywords and capture solution-aware traffic.

    But, like most SaaS companies, they faced the paradox that I mentioned above.

    There are plenty of solution-aware buyers searching for specific products to meet their needs. But getting the relevant pages to rank can sometimes be a challenge, which in turn makes it hard to capture that qualified traffic.

    Our content marketing goal for HelloSign was primarily to drive awareness at the top of the funnel and help grow the site’s authority to drive SEO for the product marketing content. 

    With this approach, we were able to create more value from the existing pages on the entire HelloSign website. Each link and social signal we generated helped give a small boost to every middle-of-the-funnel page on the product marketing site. 

    This is clutch.

    But, again, not every buyer will enter the funnel through search. 

    So, we also created some middle-of-the-funnel content that could be used through other channels like social, email, and retargeting to drive prospects from the top of the funnel further into the buying process. 

    2. Case Studies and Product Content

    We used content to drive awareness and traffic for middle-of-the-funnel prospects by creating case studies, product content, and tactical implementation guides. 

    Case studies, in particular, play a huge role in demonstrating both the versatility and range of HelloSign’s use cases as well as the massive positive outcomes that their customers have experienced by using the products.

    HelloSign's case studies were critical for driving conversions throughout the funnel.

    Fortunately, we had a great partner at HelloSign who collaborated with the product team to create impressive case studies.

    We also used keyword-optimized content on the blog to focus on specific implementations of the product for key segments and buyer personas.

    Tactical implementation posts provided actionable content for buyers as they evaluate the purchase decision.

    Now, depending on the nature of your product-focused content, it can be difficult to rank in search—but there’s a workaround. By segmenting the top of the funnel traffic, SaaS marketers can leverage retargeting and email to get this content in front of the most-qualified buyers—those who are both problem- and solution-aware.

    Once we reached this stage in our content marketing strategy, we’d built a solid collection of content to help SaaS buyers move from initial pain points to identifying solutions. For HelloSign, we used product-based content to insert HelloSign products, specifically, into the readers consideration set.

    But, there’s one more step left–that’s the actual buying decision.

    The bottom of the funnel is where the buyer scrutinizes products the most closely and determines which one is right for them.

    Bottom of the Funnel SaaS Content: Converting Prospects Into Customers

    Welcome to the bottom of the funnel.

    At this stage, the buyer is well on their way to using or purchasing a HelloSign product. 

    They have identified and articulated a specific “job” that they need to be done (pain point), discovered product solutions, features, and integrations that will work for their use case, and are now aware of specific products that meet those requirements.

    But now they have to decide which specific product or service they’ll actually buy.

    Depending on the size of the market, they could be deciding between two options or 20. The key to winning at the bottom of the funnel is creating relevant content and pages that honestly position your product as the ideal solution for your best-fit customers. 

    HelloSign’s product marketing team handled much of this content, comparing their software to competitors or alternative solutions. 

    HelloSign has no qualms with contrasting their product directly with competitors or alternative solutions.

    This type of content plays a critical role in completing the journey for buyers who are interested in HelloSign products but may be considering other options as well. 

    Keep in mind that some of the audience at this stage has followed along the entire content journey. Maybe they first discovered the company by reading a blog post that was at the top of the funnel (or even pre-funnel!)

    But others have not. 

    Maybe they were this close to making a buying decision but decided to evaluate a few other solutions. Or perhaps their procurement process requires that they perform due diligence on three possible vendors before choosing the best one.

    Whatever the case may be, this is a chance for you to reach the buyer when they are closest to making a final purchase decision. 

    And, hopefully, convert them into a customer. 


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      Seeing the Full Picture: SaaS Content Marketing 

      One of my favorite things to tell people is that content marketing is like chess–not checkers.

      To win at SaaS content marketing, you need more than just a single move in your arsenal. You need more than good content. You need more than luck.

      You need strategy.

      And part of that strategy is driven by how the specific content that you create will work together–with other content, with other marketing strategies, and with your overall market or industry–to achieve the desired outcome.

      This is what we call a framework.

      It’s the skeleton of a strategy that you can fill in with the specifics of your company, your goals, and your market. Then you have something you can execute in order to achieve your goals.

      The cool thing about content frameworks–and why I love writing and talking about them–is that they give us a shared understanding of what we are trying to achieve, what moving pieces are involved in the strategy, and how we will execute them in a way that becomes more than the sum of the parts.

      It’s like a visual guide to chess openings and scenarios. 

      From the top to the bottom of the funnel, we worked with HelloSign to build a SaaS content marketing strategy that helped them drive growth and take their business to the next level.

      While our team obviously can’t take credit for HelloSign’s overall success and ultimate acquisition by Dropbox, we’re extremely proud of the role we played. 

      By working together with their team, we were able to put together a SaaS content marketing strategy that served an important role in driving the traffic and leads that they needed to fuel their growth. 

      It’s been a fun ride and we’re excited to see what they do next. And we’re also excited to continue applying the lessons we’ve learned to helping other SaaS businesses drive massive growth through content.

      Choosing the Right SaaS Content Marketing Agency

      When it comes to driving growth through content marketing, having the right team on your side can make all the difference. 

      If you want to see results, you don’t need just keyword research, strategy, content, design, or promotion—you need a full-service content marketing partner that can handle it all.

      Optimist has been driving results with full-service content marketing for the past five years and we plan to continue elevating our clients’ businesses to new heights. 

      Our team is composed of amazingly talented designers, strategists, writers, and promotion experts. Each of us is dedicated to our craft and we come together to create custom growth-focused content. 

      We’re not generalists.

      We’re not jacks-of-all-trades.

      We’re experts at what we do—and what we do is SaaS content marketing.

      So, if you’re a SaaS founder or marketer, I’d love to chat about how we can help you reach (or exceed!) your goals. Drop me a line to let me know what you’re working on and let’s see what we can achieve together.

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