Uncommon sense: Landing the learning from your sales kickoff
Envision your ideal annual sales kickoff. It’s probably an exciting event where you rally the troops so that they’ll spend the year closing deals left and right, inevitably dominating the competition and boosting your bottom line to new heights. Right? The problem is, most businesses usually don’t experience such dramatic success.
That’s because most businesses treat their sales kickoffs as one-time events without integrating their main strategic messages into follow-up activities and training throughout the rest of the year. In fact, 71% of organizations don’t deliver any follow-up training after their annual kickoff events. So how do you ensure your company does things differently?
For your sales kickoff to yield real results, you need a well-thought-out plan for following up with sales reps that reinforces key messages and maintains the team alignment created during your kickoff.
Igniting year-round success
Big annual kickoff events can act as powerful catalysts for a successful sales year, building momentum and generating the excitement necessary to overcome the day-to-day obstacles. But sales kickoffs can’t and don’t happen year-round. They leave vast in-between stretches for expectations to be forgotten and motivation to dwindle.
However, when companies treat their sales kickoffs like springboards for the entire year and make it clear that more information will be coming after the initial event, they’ll see better compliance among the sales reps and better alignment on their teams.
The key to boosting morale and powering momentum is creating a truly engaging event that’s tied to overarching strategic goals. A sales kickoff will be hard to forget if it contextualizes the strategy in what reps really experience on the job and is coupled with follow-up trainings that bring reps back to the emotional connection they felt during the kickoff. Sales kickoffs that go beyond the event and take the strategy off the paper and put it into action help carry alignment and excitement throughout the year.
Planning Beyond the Event
To create effective follow-ups with sales teams that achieve lasting change, implement these four best practices in your kickoff planning:
1. Design a Road Map.
Don’t wait until after your kickoff to plan the follow-up. As a very first step, design a full map of every step you plan to take: where you’re starting and where you want to go, the vision driving your strategy, and the “how” you’ll need to keep sales reps informed and engaged. A map keeps your strategy cohesive and makes communicating your plans considerably easier.
Focus on significant milestones and analytics that align with your overall business strategy, and tailor the plan to fit your organization’s unique needs, processes, and culture. Make sure your map is simple enough to read quickly and easily and aligns everyone in terms of purpose and expectations so that they know the end goal upfront. After all, it’s easier to jump on board with a plan when its purpose is clear.
2. Keep in Touch Quarterly.
Keeping in touch can mean a variety of things, but be sure to check in with the sales team at least quarterly. If it makes sense, embrace a variety of ways to stay connected. This could mean combining e-learning with peer phone calls or showing videos of customer testimonials of others’ success.
Sales leaders should share updates and insights on initiatives, and sales enablement teams can help keep the momentum alive. Highlight specific wins using the learnings from the kickoff if you can. As they say, success breeds success.
3. Take Small Steps.
With each meeting or conversation, check in on progress and challenges with the strategy and adjust if needed. Don’t be afraid to adjust and involve the team in making the adjustments. Don’t expect people to change overnight, but celebrate the small changes they do make. The more opportunity to provide for them to practice the wanted changes, the more comfortable they will become with their clients and the more success they will have.
Give them time to adjust, but keep moving forward to new material. At the same time, provide opportunities for constructive conversations with peers so that sales reps can learn from one another. Peer groups can facilitate healthy accountability and help reps find clear paths to mastering new ways of working.
4. Embed New Steps in Daily Processes.
Sales reps need to know the specifics of how a new approach will look in everyday processes. Handing out a playbook at an event is a good start, but go beyond that to incorporate new and repeatable habits into the daily workflow.
Whether you’ve presented general industry insights or introduced new sales solutions, get those new ideas into daily tools like new collateral, the customer relationship management system and leader coaching conversations. Practice and exposure to the new way of doing things will help them adapt to the unique situations that constantly pop up in the field.
Event follow-up can come in many forms. Having a plan and adjusting it early and often will let you reap the benefits of your investment in a kickoff event. Keep your employees motivated through appropriate follow-up training and you’ll see improved productivity, enriched culture, and a more lucrative bottom line.
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Related content
Something has been breaking in sales for years. Alexander Group's 2024 sales compensation study found that only 49% of core sellers hit or exceeded quota in 2023, across nine industries. In software sales specifically, where the erosion tends to be sharpest, several long-running benchmarks, compiled across Salesforce, Bridge Group, RepVue, and Pavilion Revenue Collective, put median account executive quota attainment at roughly 52%, essentially a coin flip.
But here's the kicker: in that same Alexander Group study, the average seller still reached 89% of target.
Those two numbers only square one way. If a meaningful share of sellers were falling far short of target, the average would sit well below 89%. It doesn't, which means the misses across that other 51% are mostly narrow, not collapses.
49% of core sellers hit or exceeded quota in 2023, across nine industries
89% average percent of target still reached by the average seller in that same study
52% median attainment in software sales specifically, an even sharper version of the same trend
Across industries and benchmarks, attainment has been drifting down, but this isn't a story about a handful of great sellers carrying the number while everyone else is falling dramatically behind. The typical seller is getting close to quota.
Sellers aren't suddenly incapable of selling. The context around selling has changed.
Buyers still need sellers, they just need them differently
1. Sellers aren't guiding a single buyer anymore
Complex sales now involve 6 to 10 stakeholders, and the biggest enterprise purchases can involve well into the double digits. About 77% of buyers describe their last purchase as complex or difficult, a dynamic that shows up anywhere a purchase has real consideration behind it, not only in enterprise software. The seller's job is increasingly to help a group reach a decision, not simply help one person make one.
2. The seller's information advantage is shrinking
Buyers now use about 10 interaction channels during a purchase, roughly twice as many as in 2016. AI is accelerating that shift, giving buyers more ways to research, compare, and pressure-test options before they ever engage a seller. The value of simply knowing more than the buyer is disappearing.
3. Buyers can avoid seller friction for longer
A recent B2B buyer behavior study found that about two-thirds of buyers would rather not engage a salesperson until later in their process. Separately, Gartner found a smaller but still meaningful share, about a third of buyers overall and 44% of millennial buyers, who want no sales contact at all. The same pattern shows up anywhere a purchase has real consideration behind it, from enterprise software to a major purchase a family researches for weeks before ever talking to a salesperson. It's easier than ever to research a category, build a shortlist, and develop a point of view without talking to sales. That means sellers have to earn their way into the conversation by adding value, not just showing up.
4. Sellers are becoming sense-makers
Buyers aren't necessarily struggling to find information.They're struggling to determine what to trust, what matters, and what to do with it. In fact, 69% say they turn to sales reps to validate AI-generated insights.
How this changes the kickoff
All of this has big implications for the one moment each year when we bring the entire commercial organization together to prepare for the year ahead: the kickoff.
Put those four shifts together and the implication is direct. If sellers now have to facilitate a group decision instead of a single conversation, earn their way in with value instead of information, and help buyers make sense of what they've already found on their own, then two days of strategy decks, product updates, and a motivational keynote will not build any of those muscles. Most kickoffs are still designed for a seller with an information advantage. Very few are designed for a seller who must do all four of the things above.
The good news? You don't need to scrap the kickoff, you just need to redesign it.
That's work we do with clients all the time, across sales kickoffs and other high-stakes moments where strategy needs to become action.
And, in the spirit of not gatekeeping the good stuff, here's what a kickoff designed to change behavior needs to get right at each stage: before it happens, during the event itself, and in the months after everyone goes home.
Before
Start with the change, not the agenda
This is where many sales kickoffs go wrong. They start with the event: strategy update, product roadmap, messaging, breakouts, keynote. The agenda becomes the organizing principle.
Flip it. Start with the behavior you need to change, then design the kickoff around it.
That means thinking beyond the room itself: what needs to happen before people arrive, what they need to experience and practice during the event, and what needs to happen after they get back to work.
THE TEST
Can you name one behavior this kickoff needs to change, in a single sentence, before a single agenda item gets picked?
Find the real constraint
Most revenue leaders have a hypothesis about what's holding their teams back. Few have enough data to know.
We ran a readiness diagnostic, what we call a Commercial Velocity Diagnostic, for a financial services client preparing for an AI leadership event. The leadership team came in expecting the biggest barrier to be skepticism: would sellers believe AI could help them sell differently?
They were wrong.
Sellers and leaders already believed in the value of AI. The real gap was much more practical: confidence and ability. People understood the promise but weren't yet sure how to use it in their day-to-day work or bring it into a client conversation.
That changed the intervention completely. Instead of spending the event convincing people that AI mattered, we could spend the time helping them use it.
SO WHAT?
That's what a good diagnostic buys you: permission to change the plan.
A useful diagnostic doesn't need to be complicated. The version we typically run takes 15 to 20 minutes per person and, when deployed across the full population, gives leaders a ranked view of the constraints by region, function, or level, assessing everything from strategy clarity to manager effectiveness to whether the right tools are actually being used in the field.
It also gives you a baseline for the behavior you're trying to change. Without a clear starting point, there's no way to know whether the kickoff moved the needle.
Get leaders ready before the room
Leader preparation shouldn't be a briefing the night before.If leaders aren't aligned on the change, the room won't be either.
Before the wider team arrives, leaders need to understand the data, the capability gap, and, most importantly, what they need to do differently to close it.
The strongest version we've run gives leaders a dedicated session ahead of the main event. They arrive aligned on what needs to change, why it matters, and how they'll reinforce it with their teams.
THE TEST
Can every leader explain what their team needs to change, how the kickoff will help, and what they'll do differently afterward? If not, you're asking the organization to change before its leaders are ready to lead the change.
During
Get people working, not watching
Most events fail for an unglamorous reason: people sit and watch.
If you want behavior change, the room needs to feel more like the work and less like a conference.
A simple experiential architecture works:
Start with the real work. Put people into a live or simulated situation before explaining the framework.
- Let them see the gap. Pause and reflect before introducing the solution. Let the insight come from the room.
- Give them something to try. Introduce the model, tool, or methodology when people have a reason to use it.
- Practice before they leave. Don't assume understanding will translate into behavior. Let people try the new behavior while they're still in the room.
Skip the practice and you have awareness. Practice it and you have a shot at behavior change.
This isn't a small-scale idea. One global technology company runs its entire annual kickoff this way: every year, tens of thousands of sellers work through a live simulation of the coming fiscal year's go-to-market strategy before it becomes real, built with BTS. Reps are inside the situation before anyone explains the framework, they see where their own instincts fail, and they practice the year's strategy before the year starts for real. The client's own enablement leadership has pointed to an unexpected side effect: running kickoff as a shared simulation built genuine community across a large, remote, global workforce, not just skill.
Put your leaders to work too
Leaders should facilitate, participate, join teams at the tables, and model the behaviors they're asking others to adopt.
If executives are on stage for 20 minutes and gone by lunch, you've designed a broadcast.
People notice the gap between what leaders say matters and what they spend their time doing.
THE TEST
Did leaders do the same work they're asking their teams to do?
After
Build reinforcement into the work
This is where a lot of the investment quietly disappears.
Managers today are carrying more people and more work than ever before. Gallup reports that the average number of direct reports per manager rose from 10.9 in 2024 to 12.1 in 2025. Yet managers remain one of the biggest variables in whether new behaviors stick: Gallup estimates they account for at least 70% of the variance in team engagement.
So don't give managers another program to administer.
Make the first 90 days part of the design:
- Weeks 1–2: Translate the kickoff into 90-day commitments with clear owners and dates. Give leaders an executive synthesis they can use with their teams.
- Days 30–60: Bring managers together in peer groups of 6 to 8 to compare what's working. Give them simple guides they can use in one-on-ones and pipeline reviews.
- Day 90 and beyond: Connect the new behaviors to business-led check-ins and actual performance.
This isn't a theoretical sequence. In one engagement, we ran a 12-week, AI-embedded capability journey alongside a live product launch, reaching more than 100 commercial team members across 6 languages.
The results?
45% improvement in year-one launch revenue attainment vs. the prior launch cohort
63% increase in assessed manager coaching capability
SO WHAT?
That second number is worth pausing on. It measures exactly what this section argues for: managers coaching the new behavior, not just attending a workshop about it.
Make leaders accountable for what happens next
Leaders set the expectation, managers coach it, executives model it, and the organization measures it.
No platform substitutes for a manager asking about the behavior in a one-on-one.
THE TEST
90 days out, can a participant remember the last time their manager asked about the behavior? If they can't, the kickoff probably didn't stick.
The opportunity is bigger
The best kickoffs don't just get everyone aligned on the year ahead. They create a shared understanding of what selling requires now, give people a chance to practice it, and make it easier to carry that behavior back into the work.
If you remember nothing else from this piece, take this question into the planning process for your next event:
When your sellers walk back into the field on Monday, what will they be able to do that they couldn't do before?
If you have a good answer, you're probably on the right track.
Ready to redesign your next kickoff?
Let's talk about what your sellers need to walk back into the field able to do differently.
Get in touch with BTS
Traditionally, Sales Kick-Offs (SKOs) were large, centralized gatherings, designed to align teams, spark momentum, and roll out the company’s go-to-market strategy. But as global businesses expanded, that one-size-fits-all approach began to show its limits.
Even before 2025, forward-thinking companies were experimenting with more localized formats to meet rising complexity and regional nuance. As international operations expanded, centralized SKOs began to strain under the weight of market variability, logistical challenges, and cultural differences. Regional activations emerged as a way to make strategy more relevant, and more actionable, at the local level.
Then came COVID-19. Travel restrictions, distributed teams, and new ways of working forced companies to reconsider the value, and feasibility, of large-scale gatherings. Virtual and regional alternatives emerged not just as stopgaps, but as smarter, faster, more focused activations.
That shift planted the seeds for what’s now taking hold: a hybrid model, where flagship events are amplified, not replaced, by a network of hyper-local strategy activations.
Why hyper-local SKOs have gained traction in 2025
Tighter budgets, tariff volatility, region-specific complexity, and faster-moving markets have made the traditional SKO model harder to justify, at least for now. But what’s emerging isn’t a downgrade. It’s a high-impact alternative built for today’s realities.
Hyper-local SKOs offer:
- Budget-conscious impact: Less spent on travel, more invested in enablement.
- Regional relevance: Local markets demand tailored approaches.
- Faster execution: Smaller events mean shorter planning cycles and more agility.
- Stronger engagement: Intimate settings foster real dialogue, trust, and retention.
Done right, hyper-local SKOs deliver sharper alignment, deeper enablement, and faster activation, without the logistical drag.
But this approach only works when it’s connected to something bigger:
- A clear, unifying story
- A strategy that flexes by region
- Tools and experiences that build competence, not just motivation
They’re not replacing the flagship event, they’re extending its reach, bringing strategy to life where performance happens in the field.
What to consider if you’re going local in 2026
- Start with a unified strategy
Without a cohesive message, fragmentation becomes a real risk. That’s why leading companies align early on messaging, strategic pillars, and storylines, then empower regional leaders to bring them to life in context.
Centralized intent, decentralized delivery. That’s the sweet spot. - Use simulation and AI-enabled practice to scale what matters
Smaller doesn’t mean shallower. Digital tools, like AI-powered practice platforms and immersive simulations, let teams stress-test decisions, sharpen skills, and internalize strategy.
Instead of hearing strategy, reps experience it and leave ready to act. - Cut costs, without cutting connection
The savings from reduced travel and venue spend are real, but the return comes from reinvesting in high-value enablement: stronger coaching, sharper content, localized insights, and sustained follow-through.
Be thoughtful about how you redirect your budget. Spend to increase the outcome you desire.
- Match the way your teams actually sell
Modern GTM teams flex by region, segment, and product line. Hyper-local SKOs let teams focus on what’s actually happening in their markets.
It’s not just about relevance, it’s about reps feeling seen and set up to win. - Create space for meaningful dialogue
Large SKOs can default to performance over participation. Local formats flip the script. Smaller rooms enable deeper conversations and real-time alignment.
Candor goes up. Trust goes up. Impact goes up. - Move faster, stay closer to the market
Planning a traditional SKO can take six months or more. In a world where pricing shifts monthly and competition evolves weekly, that delay is a liability.
Local events can launch quickly and adjust mid-stream, by design. - It’s not a replacement. It’s a complement.
The flagship SKO still has value, especially to launch a new strategy or bring global teams together. But leading organizations are building a drumbeat of activation through local SKOs that reinforce, tailor, and sustain that initial momentum.
Think about the tradeoffs and choose a flagship SKO versus localized experience based on the desired goal of the event.
Understand the risks and how to avoid them
Hyper-local SKOs bring opportunity, but also potential pitfalls if not well-integrated. Key risks include:
- Fragmentation of message and priorities
Without a strong central narrative, messaging drifts, and alignment erodes. - Uneven quality and experience
When local teams aren’t equally equipped, outcomes vary. Some teams leave inspired. Others don’t. - Loss of cross-regional connection
Flagship SKOs build culture through shared experience. Without intentional connection, silos can deepen. - Underinvestment in enablement
If companies view local SKOs purely as cost-saving, they risk missing the moment to truly invest in seller capability. - Leadership misalignment
If local and global leaders aren’t working from the same playbook, sellers get mixed messages, and lose confidence.
How to mitigate these risks:
- Anchor every SKO to a common strategic narrative
- Equip regional leaders with tools, training, and facilitation support
- Invest in shared enablement assets like simulations and AI tools
- Create cross-regional touchpoints to build culture and community
- Track impact and reinforce key messages over time
Finding new ways to perform and adapt
In a time of uncertainty, the best sales organizations aren’t pulling back on alignment, they’re finding new ways to deliver it.
Hyper-local SKOs offer a strategic evolution: reducing spend, increasing relevance, and accelerating execution.
It’s not just a budget decision.
It’s a better way to make what matters go further.
The question isn’t “What can we do with less?”
It’s “How do we get more out of every moment?”
In 2025, sales organizations are navigating more than just competitive landscapes. They’re contending with intensifying trade tensions, evolving geopolitical alliances, and the cascading effects of global tariffs. These forces aren’t abstract, they’re showing up daily in pricing pressure, delayed shipments, shifting forecasts, and customer churn. And they’re transforming how companies approach go-to-market strategy, starting with how they design and deliver their Sales Kick-Offs (SKOs).
Tariffs are no longer edge-case scenarios. They’re sending ripple effects across every link in the value chain. Sales teams are contending with pricing instability as supplier costs swing unexpectedly. Delivery timelines are harder to pin down. Customers are pushing back on cost hikes or walking away altogether. And forecasting? It’s become a moving target. What was once considered a background risk is now a central variable in sales planning.
In this climate of constant flux, SKOs are evolving from motivational moments into serious strategic platforms. Several themes are rising to the surface:
1. Redefining “adaptability” in sales strategy
Tariffs have amplified economic turbulence. With global cost structures in near-constant motion, organizations are being forced to sharpen how, and how fast, they respond. While “agility” has been a staple of business language since COVID-19, today’s landscape demands something deeper: adaptability built on scenario planning, data fluency, and customer-centered pivots.
Sales teams are being asked to do more than react. They’re adjusting pricing mid-cycle, sourcing new suppliers, and rethinking product priorities based on margin impact or availability. SKOs need to reflect this reality. It’s not just about preparing for change—it’s about practicing for it. Teams need exposure to the messiness of mid-quarter shifts, trade-offs across functions, and pressure-filled decisions that can’t wait.
2. Flexible pricing models are pushing teams to focus on customer value
As tariff-related costs climb, many companies are left with little choice but to raise prices. But doing so without a strong value narrative is risky, especially in a market shaped by caution, cost sensitivity, and competitive noise.
Sellers can’t afford to lead with price. They need to lead with relevance. That means helping customers connect the dots between solutions and the outcomes that matter to them—faster ROI, mitigated risk, and sustained performance. The more the landscape shifts, the more essential it becomes to differentiate through clarity and confidence, not discounts.
3. Relationship-building, referrals, and longer sales cycles
In unpredictable environments, trust becomes a competitive advantage. Tariffs introduce new friction—delivery delays, price changes, procurement constraints—that sellers must help customers navigate. As buyers face more internal scrutiny, decisions slow down. Sales cycles stretch. Consensus is harder to build.
All of this puts relationship quality front and center. Sellers who understand their customer’s world, anticipate challenges, and offer real partnership—not just pitches—are the ones who earn the right to stay in the conversation. Advisory behaviors and referral networks matter more than ever. Investing in long-term trust has become a short-term differentiator.
4. Shaking things up with cross-functional insights
The effects of tariffs aren’t siloed. They ripple through procurement, finance, operations, and strategy. Sales teams without visibility into those pressures risk overpromising or missing opportunities for smarter collaboration.
That’s why more organizations are bringing cross-functional voices into the SKO. Procurement leaders are spotlighting sourcing constraints. Finance is unpacking cost structures and trade-offs. Operations is clarifying where flexibility exists and where it doesn’t. These perspectives help sellers see the system they operate within and bridge the gaps that often slow down execution—from misaligned incentives to regional friction.
5. Leveraging AI and data to support shifting targets for frontline sellers
In a tariff-impacted world, data is no longer a nice-to-have. It’s a real-time edge. As market signals shift faster than humans alone can track, AI-powered tools and predictive analytics help surface patterns, sharpen messaging, and guide better decisions.
Forward-looking companies are embedding AI into the SKO itself. Tools like BTS’s Verity give reps the ability to practice, iterate, and refine in real time, coaching them through tough conversations, pricing trade-offs, and shifting buyer behavior. It’s not about replacing reps. It’s about expanding their ability to adapt, stay sharp, and lead confidently through constant change.
6. Preparing for longer sales cycles and negotiations
As cost pressures rise, customers are taking longer to commit. Deals are dragging. More stakeholders are weighing in. Pricing discussions are stretching further than before.
SKOs are a chance to help teams get ready for that reality. Sellers need to build fluency in managing drawn-out conversations, navigating objections, and reinforcing value over time. Practicing those skills now ensures they can show up with confidence and consistency, especially when the path to close is slower and more complex than expected.
Rethinking your SKOs for shifting ground
Tariffs aren’t a temporary disruption—they’re part of a broader pattern of global instability that sales organizations must plan around. The question isn’t how to avoid the turbulence. It’s how to lead through it.
That’s what the best SKOs are doing in 2025 and into 2026: grounding teams in the real conditions they’re facing, building strategic muscle, and creating alignment across the business. It’s not about hype. It’s about capability.
Done right, your SKO becomes more than a kickoff. It becomes a catalyst—one that equips your team to win on uncertain ground.