A founder’s guide to repositioning your startup

How to shift your message without losing your customers. 

Repositioning your startup isn’t a branding exercise, it’s a business decision.

It often starts with a frustrating signal. This may be sales stalling, customers misunderstanding what you do, or new competitors taking the spotlight. 

The instinct might be to make small changes, maybe tweaking the website, but what’s really needed is a structured rethink of how you present your value, and your target customer. 

Handled well, repositioning can unlock new markets, improve conversion, and help your team sell with confidence. Handled badly, it can confuse your audience, alienate loyal users, or fracture internal alignment.

This guide will show you how to reposition with clarity, care, and consistency. 

We’ll cover: 

• How you know when it’s time to reposition
• What to keep and what to change
• How to test new messaging safely
• How to roll it out without overwhelming your team or customers
• Common pitfalls to avoid

When to consider repositioning

Most successful repositioning efforts start with tension. Something’s no longer clicking. 

You’re solving a valuable problem but the market doesn’t seem to get it, or the customers you’re attracting aren’t the ones you designed the product for.

Here are common signals it’s time to reposition:

• Your win rate is dropping, but your product hasn’t declined
• Your message attracts the wrong leads, either users who churn quickly or push back on pricing
• Your product has evolved, but your positioning hasn’t kept up
• Competitors are outpacing you, not because they’re better, but because they’re clearer
• Your sales or support teams are improvising your value prop differently in every conversation

According to a 2023 study by Wynter, 87% of B2B buyers say unclear messaging is a major blocker to purchase. 

That’s not a website issue, it’s a positioning problem.

For example, Slack began life as an internal tool for a failed game. When the founders realised people were using it to cut down on internal email and collaborate faster, they repositioned as a productivity tool for teams. 

That repositioning gave birth to a $27B business. 

If people don’t understand what you door why it matters to them, it’s not them. It’s your positioning.

What to keep and what to change

Repositioning isn’t about throwing everything out. It’s about refining what’s essential, and ditching what’s getting in the way.

Start by clarifying three things:

1. Who are your best-fit customers today?
2. What’s the top outcome they get from your product?
3. What language do they use to describe their pain points?

Then audit your current messaging. Here’s how to think about it visually:

Notion originally pitched itself as a note-taking app. 

However, as users began using it to replace docs, task boards, and wikis, they repositioned as an all-in-one workspace, thereby sharpening their value without rebuilding the product. 

“Positioning is the act of deliberately defining how you are the best at something that a defined market cares a lot about.” - April Dunford, author of Obviously Awesome 

Repositioning is subtraction as much as addition. It’s about sharpening your edge, not smoothing it out.

How to test your new positioning

Don’t update your homepage just yet. Start by pressure-testing your new positioning in low-stakes environments.

Here’s how to validate quickly and usefully:

• Run customer interviews. Present your new value proposition and ask people to reflect it back in their own words. What sticks? What doesn’t work? 
• A/B test messaging. Use platforms like Wynter, UsabilityHub, or Google Ads to test headlines and CTAs.
• Have sales and support teams trial the new story. Listen to call recordings and review how people respond.
• Test onboarding flows or surveys. Include short copy blocks to gauge comprehension and reaction.
• Workshop it with your internal team. If they can’t explain the new positioning confidently, your customers won’t either.

Good positioning is felt and understood in seconds. If it takes a paragraph to explain, it’s not ready.

Rolling out a phased repositioning

When your new positioning is tested and validated, don’t flip the switch all at once. A sudden change can confuse users, or look like you’ve pivoted entirely.

Use a phased rollout:

1. Internal first

• Brief your full team on what’s changing and why
• Update internal sales docs, messaging templates, and onboarding scripts
• Roleplay conversations to boost confidence

2. Quiet external rollout

• Update your pitch deck and test on prospects
• Make light-touch changes to your homepage and landing pages
• Share your ‘why’ in customer emails or newsletters

3. Full launch

• Announce the shift with a blog post, video, or customer story
• Update your onboarding flows, Help Centre, and app store listings
• Refresh your SEO/meta content to reflect the new language

Repositioning is a conversation, not a billboard. Roll it out gradually so your audience can come along for the ride.

Mistakes to avoid

Even great teams misstep when they rush through repositioning. Here are some mistakes to avoid. 

Don’t surprise your audience
Abrupt shifts (especially without context) confuse existing users and make new ones wary. 

Tell them why the change is happening and what’s staying the same.

Avoid jargon or vague marketing fluff
Clarity beats cleverness. Ditch buzzwords in favour of plainspoken value.

Don’t try to please everyone
Great positioning is exclusive. Trying to broaden appeal too much usually means losing sharpness.

Don’t alienate your core audience
If you’re moving upmarket or changing tone, include your early adopters in the story. Recognise them. Reassure them.

Airbnb’s early messaging focused on budget-friendly stays and couch-surfing. But this language spooked many potential hosts. 

Their repositioning toward ‘belonging anywhere’ helped shift perception and grow trust without losing the spirit of community.

“You don’t need to sound bigger than you are. You just need to sound clear about who you’re for.” - Peep Laja, founder of Wynter 

Final thoughts

Startups evolve, and so should your story.

If your current positioning no longer reflects your audience, product, or impact, don’t settle for small tweaks. A clear repositioning can unlock better leads, tighter sales cycles, and stronger team focus.

But don’t rush it. Test, involve your users, and keep your early believers in the loop. Done right, repositioning isn’t just a message, it’s momentum.