Why Headspace is Not a Failed Business?

Most startups follow the same path. They build a great product, attract users, and then try to convert them into paying customers.

However, this approach does not always work as expected.

What happens when users love your product but don’t want to pay for it?

That’s the challenge Headspace faced. Millions downloaded their meditation app, but very few were willing to pay for a subscription.

Meditation is great, but let’s be real!

Most people won’t pay for it when free alternatives exist.

So, instead of relying only on individuals to buy subscriptions, Headspace changed the game. They started making big deals with businesses.

And that’s when things took off.

The Big Idea:

Shifting to B2B Partnerships

Years ago, Headspace was just another app in the crowded wellness space to make meditation mainstream and help people reduce stress.

They had a great product.

The app was simple, beautifully designed, and provided guided meditation sessions. While millions showed interest in the app, very few bought their paid subscriptions.

Think about it. Meditation is not like streaming services or productivity tools, where users feel an urgent need to pay. Instead, it is often seen as something optional.

And that has made conversion difficult.

As a result, Headspace struggled with retention. Many users would download the app, try a few sessions, and then stop using it.

So, Headspace needed a more reliable way to generate revenue.

And to solve this problem, they focused on B2B partnerships.

Foe example, look at all the brand partners Headspace has now:

Instead of selling one subscription at a time, Headspace started making deals with companies, universities, and healthcare providers.

They paid Headspace to give access to their employees, students, or patients.

This change in strategy created a new growth channel.

Instead of struggling to get one person to subscribe, they could land a single deal and reach thousands at once.

It soon became a core part of their business. And it worked.

Behind the Magic:

Winning The B2B Strategy

Headspace realized that selling directly to consumers was not enough.

That’s when they started selling their meditation app to businesses.

That worked because it helped three different groups at the same time:

1. Employees got free access to meditation without having to pay for it themselves.

2. Companies have a simple way to reduce employee stress and burnout, which helps improve workplace performance.

3. Headspace got long-term revenue by signing big contracts instead of waiting for individuals to subscribe.

Here’s how they made it all happen:

1. They Focused on People Who Were Already Stressed

Headspace didn’t convince everyone to meditate or at least after retention struggles.

Instead, the team focused on employees struggling with work stress because they needed help already. Companies were dealing with burnout, low productivity, and high employee turnover.

Many businesses were already spending money on mental health programs, therapy sessions, and wellness perks.

However, these solutions were often expensive, difficult to manage, or not widely used by employees. And Headspace established on this.

It gave businesses a simple and effective solution. Instead of spending thousands of dollars on such wellness programs, they could offer Headspace as a benefit.

And employees could meditate anytime, anywhere, without extra effort from the company. This approach worked because it solved a problem businesses were looking to fix already.

2. They Let Companies Try for Free First

Businesses don’t spend money without proof.

They want to know if a product will make a difference before investing. Headspace understood this, so they didn’t ask companies to sign big contracts just as they met.

Instead, they offered a short free trial, called a pilot program, where a small group of employees could test the app. This method worked for two reasons:

1. Companies saw results before making a decision.

2. It removed the risk. Companies didn’t have to commit money upfront. That made it much easier for them to say yes.

Once companies saw employees using and enjoying the app, they were far more likely to pay for a full company-wide plan.

3. They Sold to the Right People

Many startups make the mistake of trying to sell to CEOs and founders. But CEOs are busy running an entire company. They don’t always focus on wellness programs.

Instead, Headspace targeted people in charge of keeping employees happy and productive - HR managers and wellness directors.

These people already had mental health and wellness budgets, making them more likely to buy a solution like Headspace.

By speaking directly to the people who make decisions, Headspace closed deals faster and avoided wasting time pitching to people who wouldn’t take action.

4. They Used Data to Prove It Works

Companies don’t spend money just because something “sounds good.” They need hard evidence that it will benefit their business.

Headspace didn’t just talk about how meditation feels good. They backed it up with research and data showing how meditation helps:

• Lower stress and burnout → Fewer sick days and better attendance

• Improve focus and productivity → Employees work faster with fewer mistakes

• Increase job happiness → Workers stay longer, reducing hiring costs

By proving that meditation could save companies money and boost performance, Headspace made the decision easy. It wasn’t just a nice perk but a wise investment.

Where It Fits:

B2B Marketing Stratey For You

If you want to sell your product or service to businesses like Headspace did, here’s a step-by-step B2B marketing strategy you can implement right away.

Step 1:
Identify Businesses That Already Need Your Product

Before you start selling, figure out who needs what you offer. Businesses won’t buy unless they already have a problem your product solves.

• Find industries where your product can improve efficiency, reduce costs, or increase revenue.

• Look at competitors who sell similar products. Who are they targeting?

• Search for companies that are already spending money on similar solutions.

If you sell an AI-powered content tool, marketing agencies, e-commerce brands, and media companies already need faster content creation.

Step 2:
Create an “Easy Yes” Offer for Businesses

Companies don’t like big risks. If you ask for a long-term contract upfront, many will say no. Instead, create a low-risk offer that makes it easy for them to try your product.

• Offer a pilot program → Let a small group in the company test your product for free.

• Provide monthly plans → Don’t lock them into a year-long contract.

• Create a clear success metric → Show them what success looks like before they commit.

If you run a SaaS tool, offer a 30-day trial for a select group inside the company. Once they see value, they will be more willing to upgrade to a company-wide plan.

Step 3:
Find the Right People Inside the Company

Don’t waste time pitching to CEOs unless they are the direct users of your product. Instead, find the decision-makers who control the budget for your product type.

• If you sell a marketing tool → Pitch to the Marketing Director.

• If you sell a wellness product → Talk to the HR manager.

• If you sell a sales automation tool → Reach out to the Head of Sales.

Instead of emailing the CEO of a large company, Headspace reached out to HR managers who were already looking for mental health solutions.

Step 4:
Use Case Studies and Data to Prove It Works

Companies won’t just take your word for it. They want proof that your product delivers results. If you don’t have case studies yet, use industry research or show real-world benefits.

• Create case studies → Show how a similar business benefited from your product.

• Use statistics → Share industry research proving why your solution is valuable.

• Highlight ROI (Return on Investment) → Explain how your product saves time, reduces costs, or increases revenue.

Instead of saying meditation reduced stress, they used research and real-world data to show how it improves productivity and reduces sick days.

Step 5:
Follow Up and Close the Deal

Most businesses won’t say yes on the first contact. They need reminders and multiple touchpoints before making a decision. Follow-ups are where deals happen.

• Send follow-up emails → If they don’t respond, reach out again in a few days.

• Offer a second call → Answer any questions they might have.

• Handle objections → If they hesitate, ask what’s stopping them from moving forward.

After a pilot program, Headspace followed up with HR teams to see how employees liked the app. Then, it turned any positive feedback into a full company-wide deal.

Resources For You

Templates: Struggling to create high-convertin g DTC ads? Get 60+ proven DTC ad templates used by top brands. Plug, tweak, and launch winning ads instantly.

Guides

• 5 types of business pitches and must-have slides

• Target audience: My tips for finding the perfect fit 

• How to write a proper email: Make the right impression

YT Video: 4 Marketing Strategies That Grew My SaaS To 7 Figures

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