How Upwork Increased Active Learning by 78%

Upwork boosts active learning with Highspot’s data-driven coaching, enhancing sales readiness and buyer engagement.

82%
recurring usage
18%
boost in buyer engagement
78%
increase in active learner rate

Introduction

As one of the world’s largest networking sites for freelance professionals, agencies, and clients, the staff at Upwork know the importance of connections. Having spent more than two decades pioneering a better way of working, Upwork is poised to create even greater opportunities as more freelancers and organizations than ever before execute projects on a global scale. To help bring its platform and solutions to an even wider network, Upwork relies on skilled sales reps supported by a team of dynamic coaches. To support its growth, Upwork partnered with Highspot to empower its coaches and thaw its frozen middle.

Industry:

Technology

Employees:

139663+

Opportunity

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 prioritizing personalized 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 organizational 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 programs.

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I recognize the impact that coaches can have when it comes to driving not just rep behavior and skill change, but ultimately revenue.

Malia Di SalvoSenior Manager of Training Effectiveness, Upwork

Solution

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 program. 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 program 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 utilizing 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 personalize 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.”

We use Highspot to ensure we can get the insights we need. It is a great asset to us as we look to measure that impact. It’s all wins for me anytime we can utilize a tool to see what’s working and what’s not.

Malia Di SalvoSenior Manager of Training Effectiveness, Upwork

Impact

Culture of Ongoing Learning Supports Continuous Skill Development

With a seamless, data-informed sales readiness program funneling 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, personalized 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 optimize rep readiness. “We’re going to start utilizing 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.

We’re looking to revamp our onboarding program and take a more progressive approach toward a true ramping experience versus an exponential curve and then a fall off. I’m excited for what we’re going to be doing. I know that it’s going to be a lot more impactful for our new hires.

Malia Di SalvoSenior Manager of Training Effectiveness, Upwork

Listen to the Podcast

Episode 51: How Real-World Coaching Helps Scale Productivity

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