5 mistakes to avoid when building a sales enablement function

This article comes from Rebecca Mann Kelly’s insightful talk at our 2024 Los Angeles #GTM24 summit, check out her full presentation here.

Have you ever had an epiphany about sales enablement, only to realize it came from making an epic mistake? If so, you're not alone.

I'm Rebecca Mann Kelly, and I've just wrapped up a 20-year career at Western Union, where my last role was leading the North American payments business, including our entire sales effort.

Before that, I had the exciting (and sometimes terrifying) experience of creating an enterprise sales function from the ground up.

Throughout my career, I've learned that every game-changing insight I've had about building effective sales enablement came from either making a colossal mistake myself or watching someone else make one.

So today, I want to share some hard-earned wisdom with you, so you don't have to make the same mistakes I did.

As Warren Buffett once said, "It's good to learn from your mistakes. It's better to learn from other people's mistakes."

So, let’s dive in!

Mistake #1: Over-indexing on CRM technology

We've all been there. You're facing sales challenges, and someone suggests, "Hey, if we just buy that big, expensive CRM software, all our problems will be solved!" Sound familiar?

Don't get me wrong – CRM technology is essential. You can't run a modern sales operation without it. But here's the thing: technology alone never solved any business problems. It's only the thoughtful implementation of a CRM that can actually contribute to the effectiveness and success to your sales enablement function.

A recent survey revealed that the greatest area of technology overspend in American companies is software licenses. And guess who's the biggest offender? CRM platforms. I'm not saying don't get a CRM, but many companies grossly overspend here without getting the value they should.

Here's another common pitfall: letting IT and engineering make all the decisions about CRM software. I love our tech folks, but this is a disaster waiting to happen.

Why? Because the CRM platform is an enabler of the sales and go-to-market strategy – it's not the strategy itself.

At Western Union, we once had five different Salesforce licenses operating simultaneously, all managed by the engineering team. It was a mess. So, what should you do instead?

Lead the requirements gathering yourself
Position yourself as the business owner of the platform
Prioritize features and set the roadmap
Articulate how the CRM enables your overall go-to-market approach

Remember, you need to take the bull by the horns and stop being a victim of someone else's CRM decisions.

Mistake #2: Building sales compensation plans in a silo

Let's talk about who should be designing your sales compensation plans. In my experience, it should be whoever is closest to understanding what customers want and what success looks like for them. And you know who that usually isn't? Your finance or HR sales comp analyst.

Don't get me wrong – I love our HR and finance teams. But they're rarely well-positioned to understand what will motivate our salespeople to excel. They're too far removed from the sales motion and the end customers.

So, what should we do instead? Let HR and finance execute the sales comp plan that we brilliantly design. Here are a few tips:

Get crystal clear on what success looks like. Talk to your top sales reps and ask what motivates them.
Find the right balance between stretching goals and making targets achievable.
Look outside your own business. Sales compensation is one of the fastest-evolving areas of sales enablement.
Consider incentivizing everyone involved in the sales motion, not just the sales folks.

Remember, the job market for talented salespeople is incredibly competitive right now. If we want to attract top talent, our sales compensation plans need to be innovative and dynamic.

Mistake #3: Neglecting end-to-end customer value delivery

This is my favorite topic, folks. When we talk about end-to-end customer value delivery, we're talking about every single touchpoint a prospect has with your company.

From the moment they become aware of their problem, through pre-sales, sales, contracting, implementation, and post-launch support – it's all part of the customer value delivery chain.

Here's a hard truth: the key driver of revenue for any organization isn't actually sales. It's end-to-end customer value delivery. How does it feel to be a customer from start to finish, at every single touchpoint? That's what drives retention and sales.

I'll never forget when I was leading a deal with Amazon, and we had a product planning meeting. I was shocked to see not just product people, but also engineering, tax, treasury, compliance, legal, and privacy officers all in the room.

They were all advocating for the customer experience! That's when I realized – this is what it means to be truly customer-centric.

So, how do we make this happen in our organizations? It's not easy. In fact, it's probably the most difficult thing I've ever done in my career. But it's worth it. Here's what you need to do:

📈 Inventory every customer touchpoint in your organization

💡 Get everyone to understand how they impact the customer experience

🔨 Break down departmental silos

🎯 Make customer experience the primary metric for success

When our prospects and clients can no longer see our internal silos, that's when we've reached true success.

Mistake #4: Outdated sales training approaches

Be honest – have you ever seen a salesperson genuinely excited about sales training? I haven't. But that doesn't mean it's not crucial. If your salespeople aren't wildly successful, the first place to look is your sales training approach.

So, how do we make sales training something our team actually looks forward to? Here's what worked for me at Western Union:

Pull aside your best salespeople and pick their brains. How do they overcome objections? What are their secret sauce ingredients?
Package these insights into training that will blow your team's minds.
Train more than just your sales team. Everyone who touches the sales motion needs training.
Invest in top talent for your sales training team. Don't leave it to junior staff who've never closed a deal.

The goal is to create training that's so valuable, your sales team is clamoring for more. It should feel like you're giving them the keys to change the trajectory of their careers.

Mistake #5: Weak feedback loop between sales and product teams

This is my biggest pet peeve. I've never seen an organization that didn't struggle with this to some degree. Here's what bad looks like:

❌ Sales teams don't know the product roadmap

❌ Salespeople can't adequately discuss features and benefits without a product person present

❌ Feedback from prospects and clients about product improvements never makes it to the roadmap

Here's what good looks like:

✅ Every salesperson knows the product roadmap inside and out

✅ Salespeople understand the product so well they don't need to rely on sales engineers for every call

✅ There's a clear mechanism for feeding client and prospect feedback into the product development process

Let me be blunt: it's no longer acceptable for salespeople to not understand technology. If you're selling a tech product, you need to be able to talk about APIs, features, and functionality without constant hand-holding from the product team.

We need to create a robust feedback loop between sales and product/engineering. This means getting these teams together regularly, breaking down silos, and ensuring that valuable client feedback makes it onto the product roadmap.

Conclusion

Everything I've talked about here is challenging to implement well in an organization.

But here's my challenge to you: be courageous. The greatest successes in my career have come from moments when I reached outside the black-and-white structure of my job description and said, "I know it's not my job, but we need to solve this bigger problem."

Yes, it's risky. Yes, it's time-consuming, and yes, you might ruffle some feathers. But the pivotal growth points in my career have been when I decided to serve the customer, not just my functional area.

So, I challenge you to be a courageous leader. Step outside your silo. Take risks and drive larger organizational change. It will make a difference to your customers, and it will make a difference in your career.

Remember, we're not here to be people-pleasers at work. We're here to serve the customer. So let's break down those walls, build world-class sales enablement, and create experiences that truly serve our customers.

You've got this!