# Positioning Against an Incumbent

> How SaaS challengers can position against an established incumbent, including choosing the angle, segment focus, migration messaging, comparison content and avoiding attack marketing.

Source: https://comppound.com/blog/positioning-against-an-incumbent (published 2026-09-14)

Competing against a well-known incumbent is one of the hardest positioning challenges a SaaS startup can face. The incumbent has brand recognition, a large customer base, a long list of features and deep integrations with the tools buyers already use. Many buyers will choose it simply because it feels safe. There is a familiar saying in enterprise software that nobody gets fired for choosing the market leader, and it captures a real dynamic: picking the obvious option protects the buyer if things go wrong.

Challengers rarely win by trying to match the incumbent on every dimension. A startup that tries to be a slightly cheaper copy of the leader usually ends up competing on the leader's terms, which is a fight it cannot win. Successful challengers change the comparison. They redefine what matters to a particular group of buyers in a way that makes the incumbent's strengths less relevant and the challenger's strengths decisive. This article explains how to understand why customers choose the incumbent, how to choose a positioning angle, how to communicate it, how to reduce the perceived risk of choosing a challenger and how to win deals against the leader.

As an example, we will follow the founders of a startup building a customer relationship management tool for small creative agencies. The market is dominated by a large CRM platform that serves almost every kind of business.

## Understand why customers choose the incumbent

Before choosing a position, understand why buyers pick the incumbent in the first place. Common reasons include safety, because the incumbent is the default and choosing it requires no justification; features, because it covers a broad range of capabilities; integrations, because it connects with the rest of the buyer's tool stack; and familiarity, because many team members have used it before at previous jobs.

Equally important, understand why customers leave the incumbent or complain about it. Common frustrations with large incumbents include complexity, since products built for everyone carry features most customers never use; cost, especially as customers add seats or modules; slow or impersonal support; poor fit for specific segments whose workflows differ from the mainstream; and outdated workflows that reflect how work was done a decade ago.

Reviews of the incumbent on software review sites, discussions in professional communities and conversations with your own prospects and customers reveal these patterns. For the agency CRM, reviews from agency owners repeatedly mention that the incumbent is built around sales pipelines rather than client relationships, that setting it up for agency work requires extensive customization and that it becomes expensive as the team grows.

## Choose your angle

Several positioning angles work for challengers. The right one depends on where the incumbent is weak, what your product does well and which buyers care most about the difference.

### Simplicity

Position as easier to set up and use. Many buyers, especially smaller teams, are frustrated by complex products that take months to configure and require training. A challenger can promise everything a small team needs without the months of setup. This angle works when the incumbent's complexity is a genuine, widely felt pain.

### Specialization

Build for a specific segment that the incumbent serves poorly. A product designed specifically for agencies managing several clients at once, with workflows built around client accounts, projects and retainers, can be far more useful to that segment than a general CRM customized to approximate it. Specialization is often the strongest angle for challengers, because large incumbents rarely rebuild their core product for a single segment.

### Modern approach

Position around a newer way of working, technology or philosophy. A challenger might build around automation instead of manual data entry, or around collaboration instead of individual records. This angle works when buyers recognize that the old way is outdated and are ready for something different.

### Price and transparency

Offer clear, predictable pricing without long enterprise contracts or complicated add-ons. This can attract buyers frustrated by the incumbent's pricing. Be careful relying on price alone, since an incumbent can lower prices or introduce a cheaper plan.

### Service

Offer more personal, responsive support and hands-on onboarding. Small companies can give customers direct access to experts and even founders, which large incumbents rarely match.

For the agency CRM, the founders choose specialization as their primary angle, supported by simplicity. Their product is the CRM built for agencies, ready to use out of the box, without the customization a general CRM requires.

## Reframe the decision

The most powerful positioning changes the question buyers are asking. If buyers ask which CRM has the most features, the incumbent wins. If buyers ask which CRM fits the way agencies actually work, the challenger has a strong answer.

Help buyers see the decision differently by naming the problem the incumbent creates for your segment. For agency owners, that problem might be spending weeks bending a sales-focused CRM to manage client relationships, then still tracking key information in spreadsheets. Once buyers recognize that problem, the incumbent's broad feature list matters less than whether a product fits their workflow from day one.

## Communicate the position clearly

Carry the position through every part of the marketing. The homepage headline should state the position plainly, such as describing the product as the CRM built for creative agencies. Product pages should show workflows specific to the segment. Content should address the problems the segment faces. Sales conversations should reinforce the same message.

Comparison pages can be particularly effective. A fair, honest page comparing your product with the incumbent, explaining where the incumbent is strong and where your product fits better, helps buyers who are evaluating both. Acknowledging the incumbent's genuine strengths makes the comparison more credible. Buyers distrust comparisons where the challenger wins every category. Content that answers the specific questions your segment searches for, built through an [SEO growth program](/services/seo-growth), helps buyers discover the challenger before they default to the leader.

## Reduce the perceived risk

Because buyers often choose the incumbent for safety, a challenger needs to reduce the perceived risk of choosing something less familiar. Several tactics help. Show proof from similar customers, such as case studies and testimonials from agencies like the prospect's. Offer free trials or pilots so buyers can test the product without a long commitment. Provide migration help, since the effort of switching from the incumbent is a major barrier. Offer flexible contracts, such as monthly plans or short initial terms. Be transparent about your company, team and roadmap, so buyers can judge whether you will be around in a few years. Highlight integrations with the tools your segment uses most, so buyers know the product will fit into their stack.

For the agency CRM, offering to migrate a prospect's data from the incumbent at no cost removes one of the biggest obstacles to switching.

## Win the deals

In sales conversations, focus on the buyer's specific situation rather than a feature-by-feature comparison. Ask about the problems they face with the incumbent or with their current process. Show how your product addresses those problems directly. Be honest about where the incumbent is stronger, and explain why that strength may not matter for them.

Target buyers who are most likely to value your position: those frustrated with the incumbent, those in your specialized segment and those who have recently experienced a trigger, such as a failed implementation or a price increase. These buyers are already open to an alternative.

## Use customers to tell the story

The most persuasive voice for a challenger is a customer who switched from the incumbent. A short story from an agency owner who spent months customizing the large CRM, gave up and moved to the specialized product, then explains what changed, is far more convincing than anything the challenger can say about itself. It addresses the safety concern directly, because it shows that a real company like the prospect's took the risk and it paid off.

Collect these stories deliberately. When a customer switches from the incumbent, ask during onboarding whether they would be willing to share their experience once they are settled. Capture what frustrated them about the incumbent, what made them consider an alternative, what they worried about when switching and what has improved since. Use those stories on comparison pages, in sales conversations and in case studies, with permission. Encourage satisfied customers to leave reviews on software review sites, where prospects comparing the incumbent and the challenger often look.

Peer references can also help close individual deals. A prospect who is hesitating may be reassured by a short call with an existing customer at a similar agency, who can speak candidly about the switch. Keep a small group of willing references and use them sparingly, so you do not wear out their goodwill.

## Expect the incumbent to respond

If a challenger grows successfully, the incumbent may respond, by adding features aimed at your segment, lowering prices or targeting your customers. Build positions that are hard to copy. A specialized product built from the ground up for a segment is difficult for a broad platform to replicate without complicating its product for everyone else. Close relationships with customers, a strong community and deep expertise in a niche are also hard to match.

## Avoid the common mistakes

The mistakes challengers make are predictable. They try to match the incumbent feature for feature. They compete mainly on price. They copy the incumbent's messaging. They criticize the incumbent unfairly, which damages credibility. They choose a position that does not reflect a real weakness of the incumbent. They fail to address the perceived risk of switching. And they target everyone instead of the buyers most likely to value their difference.

## Bringing it together

Positioning against an incumbent starts with understanding why customers choose it and why they become frustrated with it. Choose an angle, such as simplicity, specialization, a modern approach, price transparency or service, that turns the incumbent's weaknesses into your strengths. Reframe the decision so buyers ask a question you can answer well, communicate the position consistently, reduce the perceived risk of switching and focus sales on the buyers most likely to value your difference. For the agency CRM, positioning as the CRM built for agencies changes the conversation from which product has more features to which product fits the way agencies work, a comparison the challenger can win.

## Frequently asked questions

### How can a startup compete with an established SaaS incumbent?

Choose a clear angle, focus on a segment, reframe evaluation criteria and reduce switching risk.

### Should challengers create comparison pages?

Yes, if they are honest, current and acknowledge incumbent strengths.

### Is attacking a competitor effective?

Usually not. Focus on your strengths and customer fit instead.

## About Comppound

Comppound runs SEO and AI search for B2B SaaS companies: a person sets the plan and reviews samples and every high-risk page, and AI speeds up production.

- [See SEO Growth](https://comppound.com/services/seo-growth): Buyers compare before they book a demo. Are your pages there when they do?
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