7 tips for a successful sales kick-off meeting

Sales kick-offs (SKOs) are what's known in the world of sales enablement as 'a big deal'. Yes, they're primarily about communicating your go-to-market strategy for the year ahead, and setting your sales teams up for success. But you also need to grab this opportunity to really inspire and motivate your reps, as well as amplify a positive sales culture (and we're not just talking about the after-event party).

Here are 7 tips to really get your reps engaged, bought-in... and excited to sell!

Given their importance within the sales enablement world, we’ll be focusing on:

1. Chunk it up

From features, to pricing, to messaging, to demos, to... you get the gist, there’s lots you need to communicate with sales teams. And with so many SKOs now virtual, it's even more imperative to keep your salespeople sitting up and taking notice - and that means organizing it into digestible chunks.

Instead of overwhelming them with info in one not-so-swift swoop, break it up into daily or weekly sessions (whatever works for your business size, model, products and objectives) on specific subjects.

For example:

Day/week 1: product features, benefits and pricing
Day/week 2: messaging, positioning and marketing
Day/week 3: content, etc.

"Sales kick-offs are a different animal altogether. We did our best to keep them, with chunks each day, spread out over two weeks. What we did is what I call 'follow the bouncing ball', following the sales cycle, says Bill Peterson, Head of Sales Enablement at Litmus.

"So day one, we really focused on Litmus as a company, looking towards the coming year. We also looked at the martech industry that we're in, the trends and even how Covid is related to that, and then we spent the day on product."

(Find out how Bill put literally put an original 'spin' on a sales kick-off for Litmus.)

PS - We'll be discussing this topic in detail at our summit in San Francisco. For more information, grab your brochure here

2. Use real-life anecdotes

Telling salespeople your new product or feature is great and that your audience will love it is one thing, your target market telling them is another.

But the watchword here is relevance.

At the end of the day, at the most basic level, sales reps’ only aim is to sell. The more convinced they are that what you’re telling them will actually help them to sell more, the more likely they are to sit-up and listen - and what illustrates that better than active testimonials?

So, if you have a beta version that’s been rolled out to X number of customers, pick their brains, compile their feedback, and let them do some of the pitching for you.

If you don’t have any pilot results, the next best alternative is your data. Presumably, you ran some research before going ahead with the new product or feature you’re about to launch (if you didn’t, eek!), so use those numbers to back yourself up.

For example, going in with this:

“Our research showed 65% of lost customers didn’t convert because we didn’t have this feature, so the fact we now have it will improve your odds of closing deals.”

Is waaaay stronger than:

“We’ve decided to add this feature to product X and it does this, this and this…”

Go in with a role reversal approach. This time, you’re the sellers and they’re the market. Sell your product or feature to them.

3. Make it interactive

Instead of speaking at your sales team for 15, 20 or 30 minutes, mix it up by incorporating a bit of role-play. As well as being more engaging, it’ll help them contextualise what you’re telling them and offer up some practical pitching tips, too.

Tip #1: Make sure the people involved with the role-play are up for it and enthusiastic. Two people begrudgingly and half-heartedly acting in front of a room of sales reps won’t get the results you’re after.

Tip #2: Make your reps the stars of the show. We’ll touch on this in more detail a little later on but often, salespeople are more likely to listen to other salespeople, so capitalising on this might make everyone more receptive to your efforts.

For Tanya Jeffers-McAllister, Head of Advice Center, RBC Insurance, kicking off the new year to start selling new strategies and priorities virtually is about keeping it engaging and fun and allowing people to participate.

“It’s about delivering key messages, taking a break, allowing them to settle in. And then we also have the ability for breakout rooms, so if you want to do things regionally, we provide people that opportunity in that region to break out in another room to have their discussion, and then everybody log back in and come back on to say, ‘Okay, this is what we’ve come up with’; it creates that sort of momentum."

4. Use gamification

A lot of sales departments gamify their targets and day-to-day. The first person to reach X sales might get an early Friday finish. Every Thursday they might run a prize draw. They might have an ongoing, quarterly leaderboard, so on and so forth. It's a powerful tool that motivates sales reps by tapping into their natural zest for competition!

If it works, it works, so get on their wavelength and consider adding an element of gamification to your launch. For example:

The first rep to make $XXXX in sales gets a $100 voucher, the second $75 and the third $50, or
The rep at the top of the deals closed leaderboard at the end of month one gets half a day off in lieu.

Use your imagination, factor in what works best for your set-up and of course, remember to run your idea by the departmental heads first.

5. Star your salespeople

We promised we’d expand on this point earlier, and here we are. Rightly or wrongly, salespeople (in fact, all people) can be more inclined to pay attention to their peers.

For example, while it's important to have various teams involved in your SKO to give a range of perspectives (product marketing, marketing, etc), get your reps involved by asking them to deliver all or part of it.

To be truly effective the person/people you pick should be those whose behaviors you want to encourage: top performers with credibility among the team.

6. Ask for feedback

This’ll help salespeople feel invested in the process and give you food for thought when planning your next sales kick-off.

Tip: not everyone likes sharing their thoughts in front of a room full of people so make sure you provide a more anonymous forum for them too.

Remember though, just because you ask for feedback it doesn’t mean you have to act on it but if you don’t, be sure to thank the person anyway and explain why their comments aren’t being taken any further right now.

7. Reinforce your messaging

Yes, your sales kick-off meeting is the 'big event' (whether it's in-person or virtual) - but making the core messaging from your SKO run through your day-to-day sales enablement strategy is what will really make it stick.

We're talking about trainings, coaching sessions, content assets like one-pagers and case studies, weekly email briefings. Use them as opportunities to help reiterate and validate the core values from your SKO - and to make them actionable.

As Kira Greer, PagerDuty's Global Sales Enablement/DE&I leader, puts it:

"To put it plainly, it’s not enough to have written out a belief and to preach it from the pulpit. Sometimes you do need to have the formalized structure in place to support and reinforce that belief and create specific actionable guidance on what to do and what not to do."

7 tips for a successful sales kick-off

Sales Enablement Collective