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Hey {{first_name | CS Pro}},
There's probably a doc on your laptop right now called 2027 Kickoff, and it has about 4 lines in it. The menu, the speakers, a roadmap session and a team dinner.
You're about to spend most of your enablement budget on those 1 or 2 days in January or February. And by March, your team will be running the same check-in calls and handing out the same discounts.
This week on the podcast, I'm breaking down how to turn the most wasted day on the CS calendar into the day your team's jobs actually change.
But first, today’s sponsor
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Your renewal motion shouldn’t start at 90 days out
The CS teams winning renewals today aren’t working harder when the contract window opens. They’re building toward that conversation from onboarding, with a system that works no matter who owns the account.
Gainsight built a practical guide on exactly that.
Download the guide to learn about:
Why waiting for the renewal window leaves no runway to change the outcome
The four things a modern renewal system needs to deliver consistent outcomes
How to cover long-tail and mid-market accounts that never raise their hand
Why most kickoffs don't stick
Almost every SaaS company runs a sales kickoff and funds enablement for its sellers. Very few can tell you what they spend on commercial training per CSM… and plenty spend nothing at all.
Yet your team is carrying a renewal number, an expansion number and a churn number.
Then there's the learning problem. When adults learn something in a single sitting and don't use it, they lose most of it within days. Not months, days.
It's the gym in January. Packed in week 1, empty by mid February… because nobody built a programme.
Your CSMs have been handed a commercial number with no commercial training, and you can't motivate someone into a skill they don't have.
The 4 skills worth teaching (and nothing else)
First, define the job out loud. A relationship manager is measured on how the customer feels. A commercial operator is measured on what happens to the revenue in their book.
Most teams cram 12 things into a kickoff and people walk out overwhelmed. So teach 4.
Holding a price. When a customer says budgets are tight, the first response is a question, not a number: "Before we talk about price, help me understand what has changed. Is it a budget issue or a value issue?"
Mapping the buying committee. On their top 10 accounts, add the honest column, who on this list have I never spoken to? That's your 2027 risk register.
Running a value conversation. A check-in opens with "how are things going?" A value conversation opens with what you brought.
Forecasting a book of business. Every CSM should know which accounts will grow, stay flat or are at risk, with a signal behind each call, not a feeling.
And use real accounts. The moment you bring out a fictional company, everyone's brain goes to the back of the room.
This is exactly what my half day workshops do. If you're planning your kickoff now, book a call with me and we'll find the right fit, like objection handling for renewals or check-in calls to value calls.
What to cut, and what happens after
Here's what I'd cut:
Too much stage time. If more than a third of your day is inform, you've built a conference, not a training day.
The roadmap readout. Send the recording as pre-work instead.
The number worship. 5 minutes on the target, not 50.
Icebreakers. Please, no more fun facts.
Then plan the 90 days after, before you book a venue. Training doesn't fail in the room, it fails in the weeks after.
Week 2, CSMs walk through an account in their 1:1. Week 4, role play a real objection. Week 12, measure how many accounts are multithreaded compared to January.
I learned this the hard way. Years ago I ran an away day with a big number and a video with music, and the room was electric.
Then in March, one of my strongest CSMs called an account low risk. When I asked who else she was talking to, she said just him. He left, and we lost the renewal in June.
That was on me. I made my team feel motivated instead of capable.
January dates get booked early, so if your kickoff is in January, let's chat about your agenda now.
Weekly challenge
This one takes 15 minutes.
Open your draft 2027 kickoff agenda (or a blank doc). Next to every block, write inform or practice. Practice means your team does something out loud on a real account with someone giving feedback.
Add up the minutes in each column. Then take your biggest inform block and turn it into practice on real accounts.
CSMs, ask whoever sent the invite… will we be working on our own accounts at any point?
That's it for this week! Hear the full episode on Spotify, Apple Podcasts or YouTube.
The Customer Success Pro Podcast has been nominated
Big news… we've been nominated in 2 categories at the SuccessHACKER awards. I'm up for Independent Voice, and the podcast itself is nominated too!
If you've made it this far and you find value in what we share here every week, would you mind taking 10 seconds to vote for us here? I don't ask for much, but sparing a few seconds of your week would really make the difference for me.
I hope you enjoyed this week’s newsletter.
If you have any questions or suggestions, please feel free to contact us.
Cheers to your CS success,
Anika
