How to Make Your Sales Kick-off Kickass: Practical Advice from 20+ experts
Jan 10, 2022 · 9 MIN READ
Welcome to Ocanom—a digital world built by open source engineers for safe street racing in a post-apocalyptic, neon, underground world.
No, this isn’t a product by Meta. (At least, not yet!) Conceptualized for the SUSE Sales Summit that kicked off in Monaco this month, this is how the #RaceAhead theme was brought to life.
Sales kick-offs (SKOs) are party central with high-production value. Or, as Sebastien van Heyningen, Co-Founder & President of Central Metric, a RevOps consultancy firm, aptly describes it, “SKOs are the mullets of the parties—business in the front, party in the back.”
With SKOs right around the corner, it’s all about getting the band back together for most companies. For others, virtual and hybrid SKOs are being pieced together to hype up sales teams.
‘Tis the season to prep for SKO 2022: Paging the experts
We asked 20+ experts that work at product-led companies with smaller teams and unicorns with massive teams for practical advice on how to make next year’s SKO kickass, and they delivered!
Set a clear agenda + offer sneak peeks
At the risk of stating the obvious, the agenda is the backbone of the sales kick-off and sets the tone for the entire year. Heyningen says it’s a “chance to align everybody from different departments around the same goal while also looking back to see how and why the performance over the last year was made.”
Natália Litoldo, Senior Sales Enablement Manager, Global Strategic Initiatives at Tableau, recommends having complete clarity on the goals when planning SKOs. “Is the goal to provide company updates? Opportunity for connection? Opportunity to re-energize and have fun? Plan for the year?”
At Twilio, SKOs are replaced by company kick-offs (CKOs) to announce the annual big picture priorities and metrics (BPMS). Prateek Jain, Sr. Product Manager at Twilio, shares, “We give people a sense of all that we accomplished the previous year both in terms of sales and in new products launched. And then we give people a sneak peek of all the new launches coming up in the coming year to get them excited about Twilio.”
Get creative with the theme
Steve W. Martin, a sales consultant and trainer, harps on the importance of getting it right. “After participating in more than 100 sales kick-offs as a keynote speaker, I can now attest that the first step toward conducting a successful sales kick-off starts with choosing the right theme.”
Some of Martin’s favorite themes are “Winning Together, Attitude is Everything, and Driven by Performance.” Litoldo recounts a past event, “Recharge, Reconnect & Reignite,” and recommends designing the theme around the goals and tying each session to an objective.
Use the IKEA effect to get buy-in from the reps
The IKEA effect stipulates that our brains place a disproportionately higher value on tasks we’ve built. So getting the sales team excited about the goals may be as easy as asking them to contribute.
Jain says, “(Twilio’s) reps add their projections and their wishlist of product features into various forums to influence the annual plan.”
At Takeoff, an NYC web design and development agency, “1:1s are conducted to discuss challenges and takeaways from the previous fiscal year.” shares Lenny Rozental, Founder of Takeoff.
Get feedback and buy-in from leaders
Since leaders communicate product updates, new tech integration, or new competitors, getting their feedback and buy-in is crucial. This is far more important than spending thousands of dollars on an over-the-top event.
Whisenhunt explains, “We often start from both the top and bottom. [We work] closely with revenue leadership to understand their goals for the year and any major change management we may need to leverage the event for. At the same time, we work directly with front-line managers and survey our sales reps, on the different topics that they’d like to see. It takes a bit more time upfront but ensures everyone is bought into the goals and objectives of the event!” This process is much shorter for smaller organizations of under 10 reps like RevGenius. “Set up to be a product-led company, RevGenius has a team of 6 reps where only 2 sell,” shares Jared Robin, Co-founder of RevGenius in the midst of planning their first SKO.
Use tech to make SKOs more interactive
For Zavvy.io, moving to a remote-first setting wasn’t easy on the sales team. “More than any other team, salespeople are, in my experience, used to in-person contact. And they value it,” explains Alexander Heinle, Marketing Lead at Zavvy.
“To make sure all sales functions are aligned with marketing and overall goals, we design our kick-offs to be as interactive as possible.”
Zavvy heavily relies on Miro’s collaborative whiteboarding software. It makes brainstorming and exchanging ideas quickly, while video chatting makes you feel like you are in the same room.
For the data visualization company, Tableau, Slack is the lifeblood of audience engagement during SKOs. Litoldo shares, “We use Slack for Q&As and to run fun contests.”
With its HQ in the UK, Cognism’s sales team meets in person, but for company-wide sales strategy meetings that include remote teams in the US and South Africa, Zoom comes in handy. With features like breakout rooms and the ability to measure audience engagement, Zoom is the #1 choice for many remote/hybrid companies we spoke to.
Don’t ask teams to participate in run-of-the-mill activities
In 2020, Gong organized virtual happy hours, group cooking classes, and award ceremonies. Digital Dundies, anyone?
Some other culture-building activities recommended by Gong include a pitch-off, Team Olympics, and a company version of America’s Got Talent.
You can also go the extra mile and use gamification through a solution like The Go Game. It serves a dual purpose—boosts attendee engagement and brings your agenda to life through experiential learning.
And a number of companies who have been let into Airspeed’s Preview Release are using the team connectivity app as the perfect kickoff icebreaker and way to capture memories that will live beyond the event.
Don’t turn your SKO into a sales training event
Most sample SKO agendas will tell you to focus on sales skill development. After all, the whole team is there and energized. So why not use this time to offer training?
Shabri Lakhani, CEO of SalesWorks, a RevOps services provider, disagrees. “Practically speaking, shoe-horning your sales training into a time-limited kick-off isn’t the right way to ensure that training sticks.”
Cramming learning into short 3-4 day events doesn’t leave a lasting impression since there is no way for attendees to apply what they’ve learned. This can be explained by the forgetting curve Hermann Ebbinghaus, a psychologist, discovered in the 1880s. Without reinforcement, information is forgotten rapidly —56% in 1 hour, 66% in 1 day, and 75% after 6 days.
Video-conference in a customer
What better way to help sales teams close more deals than to understand buyer needs directly? So at Close’s last retreat, they video-conferenced in one of their customers to talk about what they got out of their sales CRM, the value propositions that appealed to them, and the post-onboarding product experience.
Close recommends booking sessions with current customers to share pain points and what went well vs. what went poorly during the buying experience.
Use win/loss data effectively
But that’s not enough. “Sellers want to hear how to blow their quota out of the water. They love honesty, and they appreciate when we show our cards in terms of the research we’ve done,” shares Chris Herrin, Sr. Product Manager at BeyondTrust.
Herrin also emphasizes the importance of giving it straight to sales folks instead of using marketing terms internally to deceive or fool anyone.
Share win/loss data with non-sales teams to improve sales enablement content and tools.
Review progress regularly
At Hunch, a creative automation platform for paid social growth, progress after the kick-off is measured weekly.
“(We hold) weekly review calls with the CS team to discuss any flags or progress where the sales rep can help,” shares Filip Matekovic, Head of Marketing at Hunch. The same is true for SurveySparrow, an omnichannel experience management platform. Kaushik Vikram Balaji, Product Marketer at SurveySparrow, shares, “The sales team has a ‘Weekly Sales Connect’ with the founder and GTM team to discuss bottlenecks and progress.”
While at Takeoff, Rozental says, “bi-weekly and monthly check-ins, impromptu 1:1s show (sales reps) that we’re invested in their success.”
annual quarterly SKOs
In 2021, Mary Tafuri, VP, IBM Global Sales, reimagined the company’s SKOs switching from an annual meeting to pulling off a sales kick-off every quarter.
Speaking of the team that pulled it off, Tafuri says, “They prioritized progress over perfection and never lost sight of the end game – making it worth the time for our sales force.”
This may be impossible and unnecessary for everyone, but meeting often can improve engagement. According to Highspot’s recent “State of Sales Enablement 2021” report, highly engaged employees show a 30% point improvement in attaining their quotas.
Heyningen recommends meeting at least biweekly. “Topics from the SKO should be on the agenda of any following team meetings and manager 1:1s.”
Create opportunities for learning
At Zavvy.io, sales teams stay on track by using their in-house program called Goal Companion. Heinle explains, “Slack workflows regularly remind us of our current contributions to the overall goal and help prepare 1:1s.”
Litoldo explains that virtual engagement is a challenge that calls for more creative solutions. “[At Tableau,] there are panel discussions, meetups, peer coaching, “speed networking” and many other ways of learning besides the classic one-way presentation.”
Another way to motivate reps to learn? Gamified leaderboards that integrate with tools you already use.
Strategy > Expensive SKO
While ensuring the event’s raging success is essential, you cannot outsell a bad GTM strategy.
Shiv Narayanan, CEO of How To SaaS, a management consulting firm, says, “SKOs often resort to old school sales platitudes like pound the pavement or keep dialing for dollars while the GTM strategy is weak.”
“This sets sales reps up to fail. They eventually miss quota. Board meetings get uncomfortable. VPs of Sales are replaced. And then the cycle repeats all over again.”
What sales reps need isn’t expensive kick-offs but rather knowing that a robust GTM will help them achieve their ambitious goals.
Resources for your next SKO:
- Gong’s Free Virtual SKO Checklist
- Saleshood’s 2022 Kick-off Guide
- 10 Crucial Lessons from Brainshark’s Sales Kick-off
- SKO Isn’t The Right Time For Sales Training | SalesWorks
- The Kickoff Conundrum
Cognism’s comprehensive B2B sales tech stack