The Challenger Sales Approach to SaaS Marketing (+ 9 Examples)

The Challenger Sales Approach to SaaS Marketing (+9 Examples)

When I first started dipping my toe into content marketing in the early 2000s, I was enamored with the concepts coming from the brains of industry pioneers, like Seth Godin, Brian Clark, and Joanna Wiebe. For the record, I still am. When I first heard the term “challenger brand,” it felt like someone had finally put words to an instinct I’d been feeling in my gut but couldn’t get out of my mouth. It was the kind of marketing gold that makes you feel completely seen by a person you’ve never even met — magic. Things have evolved quite a bit in the decades since game-changing concepts, like permission marketing and inbound strategies, were first introduced. Which got me thinking, what do challenger brands look like today? After a quick Google search, I found a plethora of big-name B2C challenger brands but no curated collection of SaaS challenger brands, so I created one. This article includes nine examples (organized by three, core challenger traits) from a wide range of successful SaaS companies to the billion-dollar enterprises. No two brands on this list have the same sales or growth philosophy, but by taking a challenger approach to the way they market and sell, they’ve all experienced awesome results.

The Challenger Sales Approach to SaaS Marketing (+9 Examples)

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What is the Challenger Approach?

In 1999, Adam Morgan — founder of the brand consultancy firm, Eatbigfish — coined the term challenger brand to describe
“[A brand that] has business ambitions bigger than its conventional resources, and is prepared to do something bold, usually against the existing conventions or codes of the category, to break through.”
Morgan goes on to say that although a challenger brand is often assumed to be the industry underdog, it’s really the brand’s ability to focus on what they are challenging — not who they are challenging — that cements their challenger status. He offers examples, like Warby Parker, the innovative eyewear retailer who broke into the market with a mission to challenge overpriced eyewear. If you head to Wikipedia, you’ll find plenty of other B2C examples, including Zappos, Dollar Shave Club, and Fenty Beauty. All great brands, but none of them B2B and none of them SaaS. About a decade later, a 2011 study from the Sales Executive Council brought a fascinating new dimension to the challenger definition when they applied the term to sales reps. The study measured productivity across 6,000 sales reps from almost 100 companies. The research revealed that in sales, Challenger reps dominate the high-performers. The other four types: Relationship Builders, Hard Workers, Lone Wolves, and Reactive Problem Solvers all paled in comparison to the Challenger — with the Relationship Builders coming in last. Here’s how the researchers explained it:
“Where Challengers push customers outside their comfort zone, Relationship Builders are focused on being accepted into it… a Relationship Builder is probably professional, even enjoyable, but it isn’t as effective because it doesn’t ultimately help customers make progress against their goals.”
According to the Sales Executive Council, Challengers are defined by three core capabilities: 3 different traits to a challenger brand So what does this mean for SaaS marketers? It means that in this day in age where the barrier to entry is low and competition is high, relationship building is table stakes for SaaS brands. If you want to combat buyer skepticism and attract loyal customers, you need to take risks in your marketing and messaging. Here’s how some of the best are doing it.

SaaS Marketing: 9 Successful Brands That Are Killing It With a Challenger Approach

Challenger Capability #1: Challengers Teach Their Customers

The first notable characteristic of any challenger brand is that it educates their customers.

The first notable characteristic of any challenger brand is that it educates their customers.

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Instead of taking a classic features-and-benefits approach, challenger brands seek to deliver insight. What does that mean exactly? It means that challengers brands tend to:
  • Offer a unique (and often provocative) perspective on the customer’s business
  • Bring customers new ideas and opportunities they didn’t know about
  • Challenge customers to try something new
Let’s dive into some examples.

Example 1: Be the #1 Resource, like HubSpot

“What we want you to do is to change the mode of your website from a one-way sales message to a collaborative, living, breathing hub.” ― Brian Halligan, Co-founder, HubSpot
You can’t talk about education-driven marketing without mentioning HubSpot. Recommended Reading: A Simple SaaS Marketing Strategy For Amazing Results (+ 14 Templates) When Brian Halligan and Dharmesh Shah founded HubSpot in 2006, the goal was to change the way companies sell and grow — they never could have imagined they’d end up transforming the role of sales and marketing forever. In 2010, Halligan and Shah wrote the book Inbound Marketing: Get Found Using Google, Social Media and Blogs. If you pick up a copy today, some of the information will seem a little dated, but that’s only because of the tireless work the HubSpot marketing team has done in the decade since to educate customers on all things content marketing. Bar graph showing HubSpot revenue Today, HubSpot’s State of Marketing Reports, statistic roundups, and deeply actionable how-tos are devoured by thousands content marketing professionals every year. What started with a controversial idea about the way people sell, turned into $255,000 in revenue in 2007 and more than $15 million only three years later. HubSpot has been on the other side of startup status for years now, and SaaS marketers have evolved to newer, scrappier techniques. Still, every industry needs its behemoth brand to help break the status quo and reset the baseline. Once upon a time, that brand was nothing but a bold idea and $250K in annual revenue. Here’s how they do it:
  • Free tools – Between 2006 and 2011, HubSpot’s free Website Grader was used to grade more than 4 million websites.
  • SEO-optimized inbound strategy – According to a 2012 Quora answer from Former CMO Mike Volpe, HubSpot generated over 45,000 low-cost organic leads per month, accounting for up to 80% of their total leads.
  • The blog as an Inbound Hub – Long before content hubs were a thing, HubSpot was consistently publishing a rich library of evergreen resources via the blog.
  • Academy and Google Partner Certification – HubSpot’s free certification courses are the ultimate authority play.

Example 2: Launch a Free E-course, like Unbounce

Quote from Unbounce about listening to the customer so your product won't suffer Speaking of hub pages, let’s talk about Unbounce. After almost filing for bankruptcy in 2009, Oli Gardner started the landing page platform with a few friends. What he did next was kind of genius. Rather than create a blog or resource hub on their own website, Oli and his team created an SEO-optimized e-course on landing pages at this url: By skipping ahead to a straight authority play, Unbounce took information marketing to challenger level. The landing page course for Unbounce Here’s how SaaS Hacker’s Tom Hunt breaks it down: Block quote about neutral content generating more awareness Value? Check. Intent? Check. SEO? Double-check. Unbounce secured its challenger status by ticking multiple marketing boxes with one deeply educational campaign. By building an entirely separate domain for their landing pages course, they owned the “Landing Page” category and reached $15 million in ARR. Here’s how they do it:
  • Create a high-value e-course – Rather than consistently building out multiple content assets over time (which Unbounce also does via it’s Learn page), take a shortcut by offering the complete course in your product category.
  • Use content to pre-qualify your leads – By targeting people who are searching the term “landing pages,” Unbounce attracts leads that are already solution-aware.
  • Accelerate SEO results – Use your e-course as the ultimate hub page to bring in low-cost, organic leads for your SaaS business.

Example 3: Create a Standout Voice, like Breezy

Quote from BreezyHR about brands As marketers, analyzing case studies from other marketers is well within our comfort zone. While we can certainly learn a lot from martech companies like HubSpot and Unbounce, not every SaaS brand has the luxury of selling to enthusiastic sales reps or creative marketing types. Breezy is one such SaaS company. Recommended Reading: Customer Lifecycle Marketing: How to Attract and Retain More Customers The applicant tracking system (or ‘ATS’ as it’s affectionately known in HR circles), soft launched on Halloween 2014. Known as the ‘Trello of hiring’, Breezy started as a lean, design-driven product in a traditionally kludge HR space — a space dominated by enterprise-level competitors with very deep pockets. The majority of Darren’s marketing budget was spent on paid ads. Blog post from Breezy about the best interview process Despite the heavy competition, Breezy’s product was more user-friendly than any other recruitment system in its niche, and the company grew quickly those first three years. After shifting to feature-based pricing in 2017, Darren decided it was time to improve his marketing ROI by bringing an organic strategy into the mix. Even on the organic side, Breezy was being priced out. Enterprise competitors who had ridden the first SEO wave and newer, VC-backed startups owned the top positions for high-priority keywords. Breezy would have to do something bold to stand out. For Darren and the team, that meant creating the same mega guides everyone else was creating, but focusing on educating not only for what and how but why, with no apologies for controversial positions. Take a look at some of their best-performing headlines: Is Your Employer Brand Bull? Here’s How To Build Trust With Job Candidates Women in Talent: 13 Outspoken Experts on What Winning Looks Like Are You Making these 7 Deadly Diversity Recruiting Mistakes? Statistics about different website blogs With its fearless, anti-status quo messaging, Breezy hit 20,000 monthly blog visits less than a year after taking the blog off Medium and scored position #1 rankings for several priority keywords. Today, the Breezy blog has over 34,000 unique web visitors per month and a much more balanced marketing budget. What’s really notable is that Breezy also has the highest average engagements compared to its top five competitors (51 per article). By focusing on smart ways to use content to not only educate readers but also entertain, Breezy succeeded in building its own unique tribe in a very crowded niche. Here’s how they do it:
  • Get hyper-specific with keyword targeting – Rather than taking a blanket approach to keyword selection, Breezy focused on an agile approach — changing gears when it needed to in order to protect ROI.
  • Be bold in your messaging – For Breezy to compete, product differentiation wasn’t enough. They leveraged their unique brand voice to break down topics in a memorable and relatable way.
  • Educate and entertain – By creating evergreen educational content that was also fun to read, Breezy commanded attention and grew its authority, despite being in a noisy niche.

Challenger Trait #2: Challengers Tailor Their Sales Message to the Customer

According to the Sales Executive Council study, the second driving characteristic of a challenger is that they have a:
Finely tuned sense of individual customer objectives and value drivers and use this knowledge to effectively position their sales pitch to different types of customer stakeholders within the organization.”
By now, we all know personalization is just as important in B2B marketing as it is in B2C. The difference is, you’re communicating with three, four, or even eight internal influencers and personas. Here’s how some of the best of the best Saas brands are taking a challenger approach to marketing personalization.

Example 1: Mirror Your Customer’s Pain, like Groove

“What we did in those next two months changed the story of our company forever.” — Alex Turnbull, CEO, Groove
If you’ve ever received an email from Alex Turnbull, you know the guy has a certain knack for seeing straight into your soul. It’s not the first-person voice or the uniquely vulnerable subject matter. Okay, maybe it’s partly those things. Mainly, it’s because he’s done his research. Years ago, Alex found himself with nothing but $2,490 in MRR and a dying dream. In his epic blog article, “The Story We Haven’t Shared: How Our Startup Almost Died," Alex recalls:
“How could HubSpot, Copyblogger, Unbounce and the rest of the content marketing ‘winners’ get real growth from content, while we did — what we thought was — the same thing and got nothing?”
After blogging month after month and getting nowhere, the CS platform founder decided to back up and start again. They reached out to hundreds of small business owners asking what they really needed help with. The answers ranged from hiring challenges to cash flow challenges and everything in between. At the time, Alex and his team were thinking, “Holy shit. These people are going through exactly the same things as we are.” Bar graph with timeline and profit Quote from Alex Turnbull from Groove Rather than trying to compete with the massive amounts of customer success content flooding the internet, the team decided to peel back the curtain on their own growth story. It all started with the following email CTA: From “aha” to “oh shit”, we’re sharing everything on our journey to $100,000 in monthly revenue.” Within 24 hours, the blog had 1,000 subscribers, and the growth continued from there. Because Groove tackled multiple business pain points from day one with its content marketing, the team was armed with assets that spoke to the real needs of every type of B2B decision maker, from marketing to finance, and of course, customer support. Today, more than 250,000 people consume Groove content each month, and the company boasts nearly $5 million in annual recurring revenue.

Take a customer development approach to content.

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Here’s how they do it:
  • Take a customer development approach to content – Groove learned everything it could about its market, pulling the best possible content ideas straight from their customer conversations, rather than trying to invent them themselves.
  • Tell your founder story – People trust people, not brands. By educating its readers from a place of shared experience, Groove builds an authentic connection with leads while building awareness for their own brand story.
  • Target multiple pain points – Because Groove’s content answers a variety of business challenges, it nurtures a genuine connection with stakeholders across the buyer organization.

Example 2: Create Persona-Specific Resources, like ConvertFlow

Quote from convertflow about messages to custoemrs From visitor-specific CTAs and customizable pop-ups, ConvertFlow is all about tailoring your message to your customer. In fact, their value prop as a company is closely tied to the results ConvertFlow generates for its clients (which is estimated to be an impressive 30-80% conversion rate on web visitors). Recommended Reading: 3 Foolproof Ways to Use Negative Comments on Social Media to Boost Your Sales From passing the 100th customer mark in December 2016, ConvertFlow now has more than 10,000 marketing teams using its platform to launch campaigns without coding. Even after removing coding from the equation, the mechanics of conversion sequences can be daunting, and Ethan knew it. List of landing pages through ConvertFlow To help their customers overcome analysis paralysis and find an easier path toward taking action on using their product, Ethan and the ConverFlow team created an entire ‘Inspiration’ hub packed with landing pages and CTA templates for every type of buyer. With a central hub of plug-and-play resources, leads from every stage of the funnel can bypass the overwhelming info and get the exact tools they need to get up and running fast. With templates for everything from SaaS demos and webinars to ecommerce quizzes and exit pop-ups, ConvertFlow covers multiple buyer personas under one easily navigated content hub.

Align your product to your marketing.

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Here’s how they do it:
  • Use content to answer shared objections – Even though ConvertFlow’s customers range from enterprise marketing teams to agencies and small business owners, their content solves the key shared objection that prevents most prospects from taking action.
  • Create interactive tools and templates – With a template for every kind of buyer, ConvertFlow attracts visitors with relevant content, then immediately invites them to try it for themselves.
  • Align your product to your marketing – Like Groove, ConvertFlow focused on removing the hiccups (think: no code) from its product before adjusting its marketing to reflect that.

Example 3: Use ABM-Friendly Content, like MomentPath

Quote from MomentPath about core purpose MomentPath is an early-stage startup that’s making a big splash in the early childhood education sector. As a small SaaS brand competing for large-scale enterprise buyers at leading U.S. child care franchises, MomentPath needed ABM-style content to cater to multiple C-suite and director level stakeholders. In the beginning, they did what most early startups do; they looked at the competition’s marketing and tried to keep pace. In their niche, this meant publishing posts about the ‘X Best Circle Time Songs for Preschoolers’ or ‘What to Name Your Daycare Center’. Not exactly the kind of stuff the CEO at a 2,000 center franchise would be Googling. In 2019, they made a swift, marketing pivot to fuel their sales strategy. Rather than blogging about nursery rhymes, MomentPath created a ‘Resource’ hub categorizing content by persona: ECE Leaders, Parents, and Teachers. Resources page for MomentPath In the parent and teacher sections, you can find popular SEO-focused content on broad topics, like toddler learning activities, play-based learning, etc., but in the ECE Management section, it’s a very different story. Here, readers can find content for every type of internal influencer. Whether you’re the CFO, VP of Marketing, or Head of IT, you can access rich evaluation content that answers the key questions and objections that come up throughout the sales and onboarding process. The resource hub offers guides on digital transformation, organizational culture, employee engagement and more. If these topics sound too high level for a child care platform, that’s a good thing. The EdTech market is predicted to reach $252 billion in the near future. With that kind of money flooding the market, buyers are going to become extremely discerning. By providing practical guides on complex topics, like organizational transformation and purchasing enterprise-scale child care software, MomentPath is answering nuanced questions that have gone largely unnoticed by the competition. The result? With less than $2 million in funding, MomentPath successfully broke into the enterprise market. Today, you might find their software at your local YMCA or in some of the largest U.S.-based child care franchises. Here’s how they do it:
  • Fuel your sales team – When you focus your marketing around your sales strategy, you save yourself from making the mistake of overestimating competitive content. Drill down into the real FAQs and objections coming from your prospect and create rich evaluation content to help walk them through the process.
  • Use evaluation content – Because MomentPath’s content answers core questions for a variety of internal influencers, they make it easy for everyone to get on the same page — no matter how many stakeholders are involved in the decision.
  • Take a slow and steady approach to SEO – Fact: MomentPath’s ideal buyer isn’t going to find them via Google search. By tying SEO to brand awareness and not leads, they’re able to make smarter decisions about what content to invest in, building up traffic for high-volume top-of-funnel keywords to boost their web presence over time.

Challenger Trait #3: Challengers Take Control of the Sale

Last, but certainly not least, is the third key challenger trait; the ability to take control of the sale. According to the study:
While not aggressive, [challengers] are certainly assertive. They are comfortable with tension and are unlikely to acquiesce to every customer demand. When necessary, they can press customers a bit — not just in terms of their thinking but around things like price.”
Oof, did you say price? That’s right. Challenger brands aren’t afraid to tell customers exactly what to do in order to see results in their business and because of that, customers are likely to trust them more than they trust the brands that are just trying to “stay in front of them” with generic email newsletters.

Most customers are so afraid to lose the insights they gain from working with a challenger brand, they often see it as the one the few “must-haves” in their tech stack.

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In fact, most customers are so afraid to lose the insights they gain from working with a challenger brand, they often see it as the one the few “must-haves” in their tech stack.

Example 1: Use Blog Posts as Advertising, like Ahrefs

Quote from Ahrefs about great product If you’re following Ahrefs’s story, you already know they’ve grown from 15 to almost 50 employees and $40 million in ARR in less than five years — all with just some long-tail blogs and a $7, 7-day trial. Pretty impressive, to say the least. Despite common advice to never, EVER self-promote on a blog, Product Marketing Director, Tim Soulo, made sure every single blog post showed readers exactly how to implement a high-interest tactic inside Ahrefs. Each and every blog post answers a high-value question for the reader such as, ‘How To Get More Backlinks’ or ‘How Google’s Knowledge Graph Influences SEO’. Readers value the content so highly, they don’t care if Ahrefs shows off its product. Ratings on Ahref's about engaged content On the contrary, they welcome it. Because the truth is, after reading all about two to three results-boosting tactics, you’re ready to actually do the thing. Because Ahrefs’s target buyers are tech-bullish SEOs and marketers, they don’t even need an additional nudge from a popup. By the time they’ve read a handful of blog posts, they know what the product can do and are more than ready to pony-up the $7 to trial it. How they do it:
  • Use product-focused long tail blogs – By narrowing in on deeply specific long tail keywords, Ahrefs accelerates the buyer’s journey and gets readers to opt-in for a paid trial faster.
  • Add trial CTAs – Because Ahrefs is featured as part of the solution (using clear steps and screenshots), even top-of-funnel readers quickly become product aware. From there, you just have to make it easy for them to say yes to the next step.
  • Ignore traditional advice – Ahrefs content strategy might not work for everyone, but it definitely works for Ahrefs. Challenger brands don’t wait for someone else to give them permission for how to market their products, they know their customers, trust their instincts and experiment until they know what works.

Example 2: Coach Your Customers, like Follow Up Boss

Quote from Follow Up Boss about being close with customers Since the company was founded in 2016, Follow Up Boss has stayed laser-focused on organic growth. Less than a year in, CEO, Dan Corkill, had already established a solid customer base through referrals and word of mouth. As a 100% self-funded SaaS startup, Dan wanted an organic content strategy to match his growth philosophy. He and the marketing team stayed close to their customers. With just one customer case-study and two to three educational blog articles per month, Follow Up Boss saw a 95% increase in website visitors from 253,000 to almost 500,000 in the company’s first year with content marketing. Statistics about website visitors for Follow Up Boss Fast forward to two years later, Follow Up Boss now has over 1.6 million unique visitors annually, a 20% month-over-month increase in organic traffic to the blog, and one of the highest-engagement websites in their niche. They achieved an above-average rate of positive comments and shares across social channels — despite publishing less content than their competitors. Revenue is growing steadily, despite being one of the higher-priced platforms in their space. Here’s how they do it:
  • Stick to your guns – One of the few open platforms in their niche, the team behind one of the real estate industry’s leading CRMs refused to give in to every feature request. Instead, they stayed true to their core differentiator: powerful, distraction-free selling.
  • Sell a solution, not a product – By aligning themselves with some of the most influential agents and brokers in the industry and showing readers step by step how to replicate those results inside Follow Up Boss, prospects have all the info they needed to take the next step.
  • Tell your customers exactly how to get more business – With the recent launch of The Boss Method, Follow Up Boss provides a complete business platform that shows customers exactly how to close more leads every day, challenging them to take action.

Example 3: Sell It, like Salesforce

Quote from Salesforce about selling the model and the customer success When discussing SaaS brands that punch above their weight, you have to stop and pay homage to Salesforce. From a super scrappy start in 1999, the company surpassed behemoth brands like Oracle, Microsoft, and SAP to become the $20 billion forerunner in the CRM space. With a story like that, there’s a lot to say about their marketing (Marc Benioff’s ruthless guerilla marketing techniques are the stuff SaaS marketing legends are made of), but let’s focus on a more recent example of how this challenger brand continues to take control of the sale. Namely, Salesforce’s pricing page. Screenshot of Salesforce pricing page Salesforce’s pricing page is so specific, readers are confident to enroll without questioning their tier. It’s a beautiful example of how to handle one of the hardest aspects of SaaS growth, Challenger style. In this breakdown by Price Intelligently, you can see how Salesforce expertly packages each plan to a specific buyer persona.
“The implication of proper alignment is that your entire marketing and acquisition funnel falls into place and you end up selling the right product, at the right price, to the right person,” — Patrick Campbell, CEO,  ProfitWell.
It’s smart. It’s streamlined. It’s in control. Here’s how they do it:
  • Use an actionable buyer persona – Instead of relying on Powerpoint slides stuffed with demographics, brands like Salesforce use customer data to create pricing plans that meet the exact needs of their specific buyer profiles.
  • Structure your pricing clearly – Because Salesforce knows exactly how many users and capabilities each of their buyer personas needs, it’s easy to segment their packages according to what users really want, not what you think they need.
  • Make the next step a no-brainer – With well-segmented pricing tiers that are also clearly labeled by “Group,” “Professional,” “Enterprise,” and “Unlimited,” Salesforce does the thinking for its prospects and makes it dead easy for them to take the next step.

Ready to Become a Challenger SaaS Brand? First, Be Bold in Your Messaging

If there’s one thing you take away from these examples, let it be this: The thing Challengers know that other people don’t always seem to get is that it’s not just relationships that matter.

The thing Challengers know that other people don’t always seem to get is that it’s not just relationships that matter.

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It’s the nature of those relationships that makes a new customer decide to work with you. It’s the quality of that relationship — as measured by new ideas, hard questions, and most importantly, results — that determines whether an existing client will continue working with you or whether they’ll move on to a competitor. Are you being assertive enough in your messaging? Are you delivering new insights to help them generate more value for their business? If they dropped your brand tomorrow, would they even miss you? The truth is, we all have those friendly relationships where we meet up, exchange platitudes, and talk about the weather. The people we hang on to are usually the ones willing to tell us exactly what we need to know in order to be better.
About the Author

Brittany Ryan is a content marketer, expat entrepreneur, and ‘90s pop culture addict. She founded her high-end boutique content agency from her dining room table in Nicosia, Cyprus with two toddlers crawling around her ankles. Today, Pointed Copywriting/a> serves groundbreaking SaaS, B2B and enterprise brands in over three countries and countless industry niches.