How Headspace Accelerated Sales Cycle Time by 16%

As Headspace navigated change, Highspot’s unified solution was crucial to driving consistency while empowering flexibility.

increase in average deal size
faster sales cycle on average
decrease in rep ramp time


Headspace is a mental health app with tools for everyday life, including meditations, sleepcasts, mindful movement, and focus exercise, as well as professional coaching, therapy, and psychiatry all under one roof. Seeking to provide a more holistic solution for its customers that included both self-help tools as well as professional mental health services, Headspace became what it is today through a strategic company merger. However, with an expanded product offering, Headspace initially struggled to effectively equip, train, and coach its team on the new material. With Highspot, it found a way to not only educate and empower sellers, but better engage customers.


Healthcare & Life Sciences




Manual Processes Limited Productivity

With users in over 200 countries, Headspace has helped millions of people around the world be healthier and more productive. However, with a limited training process and such diverse collateral – especially after merging with another company – the team experienced obstacles that impeded their productivity internally. “We used to have a much more manual process when it came to training,” said Victor Wei, head of sales enablement at Headspace. “It was a matter of scheduling a meeting with a sales leader, showing a presentation, and getting immediate feedback – but that only works when your sales org is small.” Once the team grew, this manual process grew cumbersome. “It became really clunky and borderline impossible to even get calendars aligned across time zones,” highlighted Wei. 

And without a single source of truth, teams were siloed, leading to misalignment and collaboration difficulties. “Sales would say, ‘I can’t find anything. I don’t know what’s up to date and I don’t know what to send people,’” noted Wei. “And marketing would say, ‘I make all this content and sales never uses it. I don’t know what they’re using. What are they doing?’” Visibility was not just limited in terms of team collaboration, but also when it came to understanding the performance of programs and content. Headspace needed a centralized solution to streamline processes, drive alignment, and optimize performance.

We were missing the analytics – the metrics – of what's up to date and actually being used and by whom. We lacked a way to manage all that content, as well.

Victor WeiHead of Sales Enablement, Headspace


Empowering Teams With a Unified Platform

With Highspot, Headspace was able to streamline what was once a time-consuming and disjointed process – equipping, training, and coaching reps – to improve scalability. “We were able to put everything in one place with a nice interface that people actually want to engage with,” said Wei. “The team can now watch the training, use the content, and simply record their 10 or 15-minute pitch and submit it for sales leadership to review, grade, and provide feedback at their convenience.” 

This streamlined experience has helped the team bridge the gap from learning to execution, as they also have access to essential data to help hold reps accountable to performance goals. “We can say, ‘Hey, how did someone do on this two months ago?’ As opposed to remembering anecdotally, we have a record of it,” noted Wei. In fact, Headspace has been able to drive a 20% increase in average deal size and a 55% decrease in ramp time since implementing Highspot. 

This unified approach to enablement made it easier for the team to deliver enablement programs and for reps to access them, while centralizing visibility into actionable insights on what works. “With a robust search, people can find what they want and share it with clients in a way that’s really easy to track. We can see if people are actually opening these pitches and whether or not they’re actually consuming the information,” explained Wei. Ultimately, this helped Headspace increase buyer engagement by 90%.

The whole experience of finding content and sending content out has been drastically improved with Highspot.

Victor WeiHead of Sales Enablement, Headspace


Enabling Transformation and Scalability

As Headspace navigated change, having a unified solution to drive consistency while empowering flexibility was crucial. “One of the biggest things Highspot helped us with was selling within different segments,” said Wei. “Since our merger, our go-to-market motion has changed three times in the last year and a half. Throughout that transition, Highspot has helped us keep content up to date and findable so reps know how to talk about our company. It’s been really critical in the success of our sales team.” In fact, since implementation, the team has achieved 16% faster sales cycles. 

Overall, Highspot became not just a crucial part of the Headspace tech stack, but a strategic business partner that the team trusts. “Of the dozens of vendors I’ve managed over the years, Highspot is definitely one of the highest quality I’ve ever worked with,” emphasized Wei.

We are very happy with the support that they give us and the ideas they help us generate, and honestly, our team would not be as successful without the support of Highspot.

Victor WeiHead of Sales Enablement, Headspace

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