Ah, the eternal struggle: leadership develops a Go-To-Market (GTM) strategy that they think is pure genius, only for the sales team to respond with a collective eye-roll. What’s going wrong here? Well, my friend, you’re not alone. There’s often a massive disconnect between leadership’s lofty vision and the on-the-ground reality that the sales team faces every day.

So why does your sales team hate your GTM strategy, and more importantly, how can you bridge this gap before your next quarterly meeting turns into a group therapy session? Let’s dig in.

The “Ivory Tower” Syndrome: When Strategy Happens in a Vacuum

Here’s the first big problem: your GTM strategy was probably created in a vacuum, miles away from the battlefield where your sales reps are dodging bullets daily (metaphorically, we hope). Leadership may understand the broad strokes of the market, but that doesn’t mean they know the specific pain points your reps are hearing from customers.

You might be looking at high-level trends and macroeconomic factors, which are certainly important, but on-the-ground reality matters just as much, if not more. If your sales team has no input on the strategy, their ability to execute it will be significantly weakened.

Key Issue: If your strategy was created without significant input from the sales team, you’re not playing the same game. Leadership is on one field, while sales is stuck in a different stadium entirely.

Solution: Build a feedback loop between leadership and sales. Early in the strategy development process, involve sales reps who are on the front lines. Their input is invaluable. You wouldn’t design a fighter jet without talking to pilots, right? The same principle applies here.

This doesn’t mean you need to have a 20-person sales council to weigh in on every decision. Start by bringing in senior sales leaders who represent the boots-on-the-ground experience. Even a quarterly meeting or feedback session with key sales stakeholders can uncover blind spots in the GTM strategy.

Unrealistic Expectations: “Oh, We’ll Just Close 20% More Deals”

Ever heard this one before? Leadership sets aggressive growth targets, and the sales team is like, “Sure, just let me dust off my magic wand and conjure up those extra deals.” If your GTM strategy relies on lofty, pie-in-the-sky targets without realistic pathways to hit those numbers, resentment brews fast.

This is one of the quickest ways to demotivate a sales team. Nothing says “we don’t get you” quite like delivering quotas that seem detached from reality. Sales reps understand that growth is the goal, but they also know the limitations of the current market, product, or resources.

Key Issue: Unrealistic quotas and pressure on sales to meet numbers that simply don’t align with market realities.

Solution: Set achievable, incremental goals. Engage your sales team in quota-setting discussions to align expectations. A sales team that believes in the plan is a motivated team. Don’t aim for a moon landing if you’re still figuring out how to build the rocket.

An additional tip here is to create “stretch” targets—ones that push the sales team a bit beyond their comfort zone but are still within the realm of possibility. It’s all about finding the right balance between challenging and overwhelming. You want your team to feel motivated, not demoralized.

The Misalignment of Incentives: What’s in It for Me?

Nothing torpedoes a GTM strategy faster than misaligned incentives. Imagine this scenario: the leadership wants to focus on long-term customer retention, but the sales team’s bonuses are tied to short-term revenue goals. What do you think they’ll prioritize? Exactly.

Incentives drive behavior. If your GTM strategy is focused on new customer acquisition, but your sales comp plan rewards upselling existing clients, you’ll get a whole lot of upselling and not much hunting. It’s a classic case of conflicting priorities, where sales teams follow the money, even if it goes against the strategy.

Key Issue: Incentives that drive behavior counterproductive to the GTM strategy.

Solution: Align sales incentives with your strategic goals. If customer retention is the priority, bonus structures should reflect that. If new customer acquisition is the main goal, then structure compensation accordingly. The point is to make sure the incentives motivate behavior that serves the broader strategy.

Think of it this way: you can’t expect your team to focus on building long-term relationships if they’re paid to close deals quickly and move on. To fix this, create a compensation structure that rewards both short-term wins and long-term relationship-building. This might involve a blend of commission on immediate sales and bonuses for retention or account expansion.

Lack of Resources: You Want Us to Do What with What?

It’s one thing to map out an ambitious strategy, but if your sales team doesn’t have the tools, tech, and talent to execute it, frustration sets in. Asking them to hit bigger numbers without the necessary support is a recipe for burnout.

Picture this: leadership rolls out a new GTM strategy with aggressive revenue goals. But when the sales team asks for the resources to make it happen—additional staff, new tools, or better training—they’re met with silence or, worse, budget cuts. It’s like asking a boxer to win a fight with one hand tied behind their back.

Key Issue: Expecting sales to execute a GTM strategy without adequate resources.

Solution: Invest in tools that reduce friction in the sales process, whether it’s CRM software, lead generation tools, or just more bodies on the team. Don’t expect results without the right resources in place. It’s like telling your team to climb Everest but only giving them flip-flops and a granola bar.

Make sure your team has the right combination of technology and human resources. A sophisticated CRM platform might sound expensive, but it’s a one-time investment that pays off in improved efficiency and better sales insights. Also, consider providing ongoing training to ensure your team knows how to leverage these tools effectively.

Communication Breakdown: Mixed Messages from Leadership

Salespeople are often bombarded with mixed signals from leadership. On Monday, the message is to prioritize upselling. By Wednesday, leadership has shifted focus to new customer acquisition. By Friday, they’re told to concentrate on customer retention. Sales teams need clarity, not whiplash.

We’ve all been there—one week it’s about closing deals fast, the next week it’s about nurturing long-term relationships. Leadership often shifts priorities in response to market conditions, but for the sales team, that constant pivoting can be confusing and demotivating.

Key Issue: Inconsistent messaging from leadership on strategic priorities.

Solution: Define clear priorities and stick to them. Frequent course corrections confuse and demoralize the sales team. If changes are necessary, communicate the rationale clearly and explain how those shifts will help the team meet their goals.

It’s also critical to make sure that any changes in strategy are accompanied by updates to sales training and processes. Don’t just announce the change—support it with the necessary tools, resources, and information to ensure it’s successfully adopted on the ground.

One-Size-Fits-All GTM Strategy: Not All Markets Are Created Equal

GTM strategies often fail because they assume every prospect, market, or vertical will behave the same way. Spoiler alert: they won’t. A rigid, one-size-fits-all approach doesn’t allow for the nuances that different customers, regions, or industries require.

For instance, what works for enterprise-level clients in one industry may completely flop for SMBs in another. Yet, GTM strategies often overlook these crucial differences.

Key Issue: A rigid strategy that doesn’t account for variability in market conditions or customer needs.

Solution: Allow for flexibility within the GTM framework. Encourage your sales team to tailor their approach to specific prospects or markets. Build in room for deviation when necessary. Your strategy should serve as a guide, not a straitjacket.

Your sales team knows their customers better than anyone. Empower them to adapt the strategy to meet the unique demands of each market or segment they’re targeting. This could mean offering different products, messaging, or pricing models depending on the customer’s size, location, or industry.

Leadership’s Disconnect from Customer Pain Points: Who’s Talking to the Customers?

Sales reps are the ones having tough conversations with customers, hearing complaints, and dealing with objections. Meanwhile, leadership might be talking about ‘value propositions’ and ‘synergies’ in conference rooms, blissfully unaware of what customers are actually saying.

Key Issue: Leadership doesn’t understand the daily pain points that customers—and by extension, salespeople—are facing.

Solution: Get leadership in front of customers more often. Have execs sit in on sales calls or, better yet, do some selling themselves. When leadership understands the customer pain points firsthand, they’ll craft more realistic GTM strategies that are grounded in the customer’s reality.

A great way to achieve this is by encouraging cross-functional collaboration. Get the product, marketing, and leadership teams to sit in on sales calls or customer service interactions. Not only does this provide invaluable insights into customer needs, but it also creates alignment across departments, which strengthens the overall GTM execution.

Wrap Up

The disconnect between leadership and sales is one of the most common reasons GTM strategies fail to deliver. Fixing it requires a mix of better communication, realistic goal-setting, alignment on incentives, and making sure your sales team has the resources they need to succeed. At the end of the day, your GTM strategy is only as good as your sales team’s ability to execute it.

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