How Upwork Increased Active Learning by 78%

Lack of Data Limits Sales Readiness Efforts

Upwork’s primary mission is to facilitate connections between clients and skilled professionals, creating value-driven interpersonal interactions that help move business outcomes forward. Its enablement team has taken this mission to heart and is prioritising personalised coaching as a key lever to evolve reps’ sales readiness. “One of the things that drew me to Upwork was the fact that they had a sales coaching team,” shared Malia Di Salvo, the senior manager of training effectiveness at Upwork. 

To better inform coaching experiences and reinforce essential learning, the team aimed to infuse analytics into their training and coaching strategy. With that data-backed insight, they could design valuable learning experiences proven to move the needle on rep performance and organisational outcomes. Yet, without an enablement platform to capture that data, they had no way of doing so, inhibiting their ability to drive impact in the areas that mattered most. “How do you identify the most robust group of people where the marginal benefit of increasing their quota attainment by 1% will exponentially increase your revenue and productivity goals?” asked Di Salvo. 

Identifying and continually upleveling that frozen middle through ongoing, data-informed learning soon became a central goal for the team. “If we see the increase in productivity, deals, and quota attainment, it is going to drive our revenue goals in a whole new direction,” added Di Salvo. To transform their low performers, the team turned to Highspot, trusting that the unified platform’s native analytics would help them gauge, reinforce, and further hone the impact of their existing training and coaching programmes.

Data Drives More Precise Measurements of Success 

Upwork’s new partnership with Highspot was vital in helping its enablement team build an insight-driven sales readiness programme. With an 82% recurring usage rate and in-depth data flowing out from every activity, the team had the insight they needed to develop improved training and coaching strategies that would resonate with reps.  

The team took that insight to a recent training initiative: a programme called Gaining Executive Alignment that aimed to prepare reps to create powerful champions. “We had a progressive series program where we did three different live sessions with content and Plays,” shared Di Salvo. “Our content team was able to measure who’s utilising it and how it’s working. We saw a decent increase in actually getting power on deals and setting up new meetings with the right people.” Through those live training events and their corresponding content and Plays, the team created a repeatable strategy to reach executive stakeholders — and proved it worked. Designed to resonate with higher-level decision-makers, the strategy helped reps generate an 18% increase in buyer engagement.

Soon, the team took that insight to their sales coaches. Drawing on Highspot’s native analytics, they surfaced data on reps’ training completion and activity in the field, using it to shape and personalise coaching experiences. With that information, coaches could easily create valuable experiences that targeted reps’ unique struggles — a huge leap forward in the effort to thaw the frozen middle. “Now, the sales coaching side of the house can lean into that middle and focus on their productivity,” added Di Salvo. “The coaching team can really help achieve some of that productivity and those revenue goals that we have to hit.”

Culture of Ongoing Learning Supports Continuous Skill Development

With a seamless, data-informed sales readiness programme funnelling reps through essential training experiences — and reinforcing that learning with data-backed coaching — Upwork has equipped its sales teams to move the needle on its key outcomes and thawed its frozen middle. Since implementing Highspot, its active learning rate has risen by 78%, illustrating the culture of ongoing, personalised learning it has cultivated in its go-to-market teams. As part of this reinvestment in ongoing learning, the team also plans to begin mapping AI to their training and coaching initiatives to further optimise rep readiness. “We’re going to start utilising AI,” shared Di Salvo. “It’s the term of the quarter and of the year, so how do we bring it into some of our e-learnings?” To help reps old and new embrace continuous skill development from the very beginning, Upwork is making plans to further hone its existing strategy.