3 Sales Training Tips for Your Next Sales Kickoff Event

One of the things that’s so exciting about working with the sales team here at Udemy for Business is how global we truly are. We have people from throughout the US and Canada, Europe, and Asia/Pacific.

Working with such a distributed team means that we have diverse perspectives and the potential to work with customers all over the world. 

We recently gathered our entire sales team at the Udemy office in Denver for a Sales Kick-Off (SKO) event. Here’s how I designed our sales training event as well as tips for training a distributed, global sales team.

Setting the foundation: Building a learning culture

In my role as Sales Enablement & Productivity Manager, one of my Objective and Key Results (OKRs) is to foster and encourage a culture of learning within the Udemy for Business sales team. I think it’s important to create visibility and awareness into how we support learning for ourselves. We don’t just believe this is important for our customers, but for our employees here at Udemy for Business as well.

I’ve been approaching this in a number of ways. I introduced Enablement Office Hours as a forum for people to collaborate and learn from each other. We discuss what people have been doing in the past week, celebrate their successes, and brainstorm different ways of dealing with challenges.

I’m also a proponent of the Udemy practice of “eating your own chocolate,” which is our way of saying that we use our own product. I’ve created Udemy for Business courses for my team using our course creation tool, and have leveraged existing Udemy for Business online courses for onboarding and upskilling. This keeps training content accessible to members of our team who live in different time zones and can’t attend live sessions, but it also makes it easier for people to go back and rewatch content if there’s ever something they’d like to revisit. 

I think it’s important to mention that I don’t just develop training on my own—it’s a collaborative effort with others on the sales team, as well as cross-functional teams. I’ve surveyed the team multiple times and worked with the managers continuously to match my programs to their goals and outcomes. 

Fostering connections and continuous development 

At our recent Sales Kick-Off (SKO) held at our Denver location, I was thrilled to be involved in planning and developing the curriculum. We gathered our entire global sales team and some other UFB leaders and executives for two full days of training and development. 

For our Sales Kick-Off training, we decided to develop two specific workshops: one on social selling (using social media to build relationships and ultimately make sales) and one that focused on an outbound selling playbook. 

1. Social selling

Social selling has been proven to be very effective as a means of communication and introduction to contacts you’re trying to bridge the gap with—78% of people who engage in social selling are outselling their peers who aren’t using this tactic.

I organized people into 14 tables with 7 people at each table and intentionally grouped everyone truly heterogeneously because I wanted to make sure that no one sitting at a table knew each other. This gave everyone the chance to get to know the other people at their table and learn more about the different roles and markets within our team. 

We started the training with a presentation from our Senior Director of North American Enterprise Sales, Sean Masterman. Sean got up on stage and talked about the importance of social selling. 

After Sean went through his slides and presentation, he asked everyone in the room to pick up their phone and make sure they connected with everyone else in the room on social media. Then he had everyone do an exercise of finding someone on social media and building out their introductory messaging. After everyone had a chance to work on their own, he asked them to share with the person next to them, and then asked for volunteers to share with the whole group. 

I’ve also seen much more activity in our internal Slack channel with people sharing and commenting on different social selling resources. It was impressive to see how quickly everyone was applying the concepts they’d learned in the workshop. 

2. Launching a playbook

Our workshop on implementing an outbound playbook followed a similar structure, but with one key difference. We’d assigned an exercise ahead of time, so everyone came to that session with a list of accounts that they’d identified that met specific criteria.

Having participants complete pre-work meant that in this session, they had the opportunity to dive in and try out the techniques they’d been learning throughout the training such as developing an email cadence for their target list. 

On Wednesday, people had time to put that cadence into action, finalize the email, and actually send it. And then we had our Enablement Office Hours a few days later on Friday, so we were able to talk about people’s strategy, what they’d done, and what they were going to do next. I think one of the most important lessons from this session and the following Enablement Office Hours was not to give up after the first try, and that reinforcement of a learned practice will ensure application over time. Different members of the team have different approaches and it was exciting to hear them share their tips and tricks with each other more readily after the SKO.

3. Reinforce learning with online courses

A key follow-up to promote continuous learning post-event was to recommend a curated learning pathway of online sales skills courses on Udemy for Business. Online learning is a great way to continue training for our global, distributed workforce. 

Every month, our company hosts DEAL or “Drop Everything And Learn” hours which carves out time for our sales employees to dedicate to learning and improving their skills at their own pace. 

There are excellent general sales courses on Udemy for Business to help newer salespeople develop their overall skills such as Sales Training: Practical Sales Techniques. 

We also have more specialized courses for salespeople who’d like to develop specific skills. For example, for focusing on outbound messaging skills, Lead Generation Machine: Cold Email B2B Sales Master Course is great. This course helps learners develop results-oriented templates and scripts and generate consistent leads via email. Similarly, for salespeople who’d like to hone their cold calling skills, I recommend Cold Calling for B2B Sales: How to Prospect over the Phone. This course—aimed specifically at B2B salespeople—covers everything from leaving effective voicemail messages and turning gatekeepers into allies to identifying common objections and securing appointments.

The Sales Kick-Off training provided a valuable opportunity for us to gather our global team in one room, to learn more about each other and our roles, share sales best practices, and experiment trying out new ideas in the wild.