How Dropbox Boosted Attainment by 57 Percentage Points

Disconnected Technology Limits Sales Productivity

Disjointed enablement technology meant Dropbox’s sellers were plagued by tool fatigue, struggling to make progress in a disconnected and difficult to navigate digital environment that actively impeded productivity. Seeing the negative impact on its sales teams, Dropbox sought a way to not only streamline reps’ workflows but also build a more robust sales readiness program. However, the usual constraints on time, resources, and bandwidth made it difficult to evolve its training and coaching arm. “Training is only as good as the reinforcement that happens afterward,” explained Felix McCabe, head of global enablement execution at Dropbox. “The challenge is often that there’s not enough time to coach each rep effectively, especially when managing a team of six or eight reps.”

With a new product launch on the horizon, the team knew they needed a new approach to training and coaching. Ahead of the launch, every rep needed to be primed and ready to land the new product, something their existing solution couldn’t help them achieve. As they evaluated their options, they sought a unified platform equipped to simplify workflows and deliver holistic, scalable support — improvements they were confident Highspot could deliver.

Unified Platform Powers Readiness Ahead of Product Launch

With Highspot up and running, content was easier to find and curate. “Governance is as much about curation as creation because you can have a lot of content,” McCabe shared. “It’s about building good governance around the platform to make sure it’s always quality content and outdated things are removed.” This swift focus on governance led to a 90% content findability rate and provided a strong foundation from which the team could build as they approached launch day.

 With Highspot serving as a single source of truth, the team immediately leveraged it to support the creation of a more robust sales readiness program. For the launch, they created a three-module Learning Path that shared essential knowledge and encouraged reps to put it into practice.

From within this new Learning Path, sellers could study the nuances of the product and put new messaging into practice, simultaneously furthering their learning and verifying their ability to implement it in the field. “Alongside that, we’ve created an evergreen space around the new product, with pitch decks, discovery questions, case studies, and competitive information,” explained McCabe. “We’ve even got video content from some of the reps who’ve been successful in selling the product and what value they were able to bring to their customers.” With training and self-led coaching experiences powering rep learning and boosting Play adoption by 10%, the team could feel confident that reps had everything they needed to successfully take their new product to the market.

Empowered to Accelerate Impact At Scale

With a more robust readiness program building competence, Dropbox has seen a significant uptick in performance in the field — a big win in the early days following its new product launch. As the enablement team began to quantify their impact and understand the value of Highspot, the numbers said it all. 

As Dropbox builds stronger processes to drive performance in the field, it intends to stretch into real-world coaching to scale its efforts further. “We’re never in a fair fight in enablement,” continued McCabe. “We’re typically outnumbered 50 reps to one of us. In that world, it’s all about being scalable, repeatable, and measurable.” 

To continue the growth, the team is laying plans to grow alongside Highspot. “We’re hopefully going to accelerate a lot of what we’re doing with the AI functionality Highspot has brought to market recently,” concluded McCabe. “That’s going to be a big piece for us.”