5 Ways to Deliver a Truly Impactful Sales Kickoff

Joe Andrews

We just wrapped up sales kickoff (SKO) season. Typically, in January and February, depending on fiscal calendars, we all see pictures of salespeople in our networks posting party pics from Las Vegas or some other city’s convention center. We know they’re having fun, but how are they learning and preparing for a successful new selling year? And how do we, in turn, ensure our own sales kickoffs are effective?

We recently completed our sales kickoff at InsideView. The three-day agenda combined information sharing, skills development, team workshops and fun, which I’m sure sounds pretty familiar. The event was a culmination of thorough planning and conscious decisions about the learning objectives, content, fun and logistics. The end result was the highest ratings and engagement scores in InsideView’s history. While the real proof of success will be in terms of 2019 revenue results, here are five key takeaways we’ve found to drive effective learning and engaged sellers:

Push sellers out of their comfort zone (and make it a safe space)

Sales skills like how to have a good discovery call, pricing and negotiation is like physical exercise – you need to learn the techniques from subject matter experts (SMEs) and then practice repeatedly to gain muscle memory. Part of that is mixing it up so it’s not staid and the exercises are not too easy. To that end, we disrupted expectations (especially among experienced sellers) by throwing them into new situations e.g. to practice a discovery call with little time to prepare/research the account they were calling. This was uncomfortable at first, but enabled sellers to focus on conversational skills by asking the right questions that generate buyer interest and engagement and qualifying the opportunity.

Incorporate different perspectives into training teams

This sounds pretty basic but in many sales kickoffs, aside from large general sessions, teams for training workshops are broken out by segment (geography, size, industry, function, etc.) into similar “birds of a feather” groups. In our case we consciously mixed these teams e.g. fledgling sales development reps with seasoned enterprise reps, new business-focused account executives (AEs) with customer success managers (CSMs), reps from Asia Pacific with North America. There was skepticism at first but in the end we heard clear feedback that sellers gained new perspectives and learned a lot from their peers on different teams.

Teach the product roadmap through the eyes of your customers

All sales kickoffs have a shared element of “corporate information sharing” where key executives share high-level business strategy, financial plans, and the product roadmap of what new functional capabilities are coming this year. While most of this information is vital for customer-facing representatives of your company, it tends to be shared “inside-out” through the lens of how you, the vendor, see the world. In the best sales kickoffs I’ve been a part of, we flipped this information sharing around so sales reps can learn and understand it from their customers point of view. In InsideView’s case, we had our product management leader co-present with our head of customer success who regularly shares the roadmap with her customers. She was a voice for our customer’s perspective, insights and anecdotes that only she could share, and our sellers gained richer knowledge that they could immediately apply to their own customers about the key problems we were uniquely qualified to help them solve. It was a magical moment to observe this interaction as light bulbs repeatedly turned on for our sellers.

Strive for “Goldilocks” balance

As in “just right”...  the right balance of challenge/fun, celebration/critique, exorbitance/frugality. This is different for every company, of course and likely driven by the preceding year’s success, prospects for the new year and the tone that sales management wants to set. In InsideView’s case, we’d gone back and forth over the past few years between large scale/scope/budget/bold agenda and conservative/scaled back. Agenda questions included whether or not to bring in outside trainers and leverage 3rd party content - e.g. a prescriptive sales methodology like Sandler. Like most sales organizations, we also have sellers with different levels of experience. We needed to decide if we include intro sales 101 training for our newer sellers in addition to advanced topics. Some stakeholders believed if we didn’t invest a minimum threshold that it wouldn’t be worth doing at all. Others believed any investment about a bare minimum would be wasted. This year we made a conscious decision up front in our planning to be in the middle ground or “just right.” We incorporated some outside content and also had our fair share of good food and entertainment. We just didn’t overdo it.

Keep momentum going post SKO

As the main event is literally a kickoff to the year, it’s critical amidst the energy and exuberance following the event to stay grounded and focused on continuing to enable your sellers in the quarters to come. The week after we returned from Insideview SKO, the first thing we did was a comprehensive survey where we measured the effectiveness of the event, content, logistics etc. The second thing we did was discuss a go-forward enablement plan with all our sales leaders and CRO. We emphasized the skills we want to double down on training over the next few quarters and what content / learning gaps still remain. This process built further trust between sales leaders and our enablement team. While we just delivered a highly rated event that was popular with our sellers, we’re not stopping there. We’ve got each others’ backs and will help our sellers throughout the year to hit our shared revenue and quota achievement goals. In the end, that’s what matters most.

Joe Andrews is vice president of product and solution marketing, and runs sales enablement for InsideView, a company that helps B2B companies define go-to-market strategies and drive rapid market growth with its targeting intelligence platform. Follow him on Twitter, @AndrewsJoe and find him on LinkedIn at www.linkedin.com/in/joeandrews/