How O’Reilly Media Reduced Ramp Time by 66%

Maturing Function Requires More Scalable Support

The enablement team at O’Reilly Media laid the groundwork for the robust function that exists today. “Sales enablement was a function we started about five years ago,” began Allison Gillespie, vice president of marketing at O’Reilly Media. “We built it from the ground up.” Since then, the team has continually evolved the function to suit the changing needs of the business. A previous enablement solution supported these early efforts, but as time went on, it began to create more and more snags in day-to-day operations. The breaking point came during a period of explosive growth when O’Reilly Media began to expand its sales force. “The company started rapidly growing, which meant the sales team was rapidly hiring,” explained Gillespie. 

Existing snags grew into major gaps, which only widened as new sellers were brought into the organization. The team again needed to evolve their operations, but the previous solution had reached the limit of what it could support. As the team began the search for a new solution, a few key priorities emerged — namely, one that could grow alongside O’Reilly Media. That, and a solution that could help formalize the onboarding process and build foundational knowledge in a more standardized manner. “At the time we just had one person on our team that was doing ad hoc onboarding,” continued Gillespie. “We realized it was not going to scale.” 

Onboarding wasn’t the only area in which the team saw an opportunity for growth. Their previous solution had also struggled to surface content and context with sellers, which placed undue strain on sellers’ time. “We need a home base for sellers,” added Keith Swafford, senior sales enablement manager at O’Reilly Media. “Do we have a spot where sellers can say: ‘I have what I need, and I know where to find it?’” That the previous system could not act as a legitimate single source of truth was telling — it was time to make a change. As O’Reilly Media took the next step in its maturity journey, it made the switch to Highspot.

Instilling New Rigor Into Skill Development

As new sellers joined O’Reilly Media on a more regular basis, the enablement team focused on standardizing knowledge and seller behavior. The formalization of the onboarding process was priority number one. To do so, the team leveraged training capabilities in Highspot to build out a standardized program. “We streamlined the onboarding process,” explained Gillespie. The new program saved sales managers significant time, as new hires entered with the same understanding of the organization, its selling environment, and its processes. “We took a huge chunk of work off sales managers’ plates,” continued Gillespie. “It’s more of a joint effort. Enablement starts, then we hand it back to the manager.”

From there, the team kicked off efforts to cultivate more consistent execution by investing in the Challenger methodology. Using the Highspot Marketplace, they integrated it directly into the platform and rolled it out immediately. “We moved to the Challenger methodology and put our entire sales team through the training,” noted Gillespie. With methodology content and training available in Highspot, sellers quickly adjusted to the new selling style. “It’s shifting us from feature-based selling to teaching sellers about what our product or service solves,” enthused Gillespie. As sellers use the methodology in day-to-day engagements, they now know to lead with value, a new approach that has resulted in an 8% increase in buyer engagement.

A major contributor to the success of these efforts was the team’s ability to ensure every learner received only the support most relevant to them. “Highspot’s ability to fine-tune our sales messaging and positioning has been really strategic,” enthused Swafford. “If we want to create Sales Plays, specific courses, or certain materials, we can distribute it across our groups with way more precision and accuracy.” With Highspot, O’Reilly Media’s enablement team matured their function and, once again, rose to the occasion to support the business. 

Future-Proofing the Function for Further Evolution

Through the enablement team’s efforts, O’Reilly Media has found that its sellers execute with new consistency and proficiency. It has created a culture of ongoing skill development through its methodology investments and is empowering its sales force to more rigorously pursue further growth. Streamlined onboarding efforts have paid dividends in reduced ramp time and improved new hire velocity — since it rolled out the new onboarding program, ramp time decreased by more than 66%. “We were able to reduce the ramp time for new reps,” concluded Gillespie. “What used to be six months ramp time to get reps out there selling is now down to 60 days or less. Depending on the role, they’re hitting the ground running and sometimes actually closing deals within 30 days.”

At O’Reilly Media, the enablement flywheel is going, propelling faster and faster with each passing day. Highspot has become a ubiquitous feature of its operations, with 91% recurring usage of the platform across its users. As every seller executes with greater precision and expertise, they are prolonging the growth moment and securing O’Reilly Media’s future potential — the impact of partnering with a solution built to scale.