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What if I told you cross-selling doesn’t start with targets and incentives…but with the very first 90 seconds of your sales rep’s elevator pitch?
We all want our sales teams to increase wallet share and build deeper customer relationships.
Cross-selling is essential to achieving that.
But here’s the uncomfortable truth I’ve noticed over the years:
Most cross-sell efforts don’t fail because of pricing or product gaps.
They fail much earlier… when the sales team can’t deliver a strong, holistic elevator pitch.
Let me explain what I mean.
The Hidden Cross-Selling Killer: Your Elevator Pitch
Cross-selling failures don’t happen during the negotiation stage.
They happen in the first meeting.
In those first 90 seconds when your rep opens their mouth.
Because here’s the thing — that initial pitch sets the boundaries for every single conversation that follows.
If you position yourself narrowly in that first interaction, the customer will forever see you that way.
It’s like being put in a box, and once you’re in that box, it’s incredibly hard to get out.
Example: Your cybersecurity rep only talks about cyber in the elevator pitch = you’re forever “just the cyber guys.”
The customer will never think to call you for cloud services, data management, or managed IT services.
Why? Because you never told them you do those things.
Your elevator pitch is where you earn — or lose — permission to cross-sell later.
Average Reps vs. Great Reps: The Positioning Gap
Let me share a small learning I’ve gathered over the years working with hundreds of sales teams.
Average reps sound transactional:
They focus only on their specific product or service line.
“Hi, I’m John from XYZ Corp, and I handle our cybersecurity solutions.”
That’s it.
That’s all the customer hears.
And now John has created a single-threaded relationship where he can only talk about one thing.
The customer doesn’t know — or care — about the other 5 service lines the company offers.
The result?
- Narrow positioning that limits future expansion
- Customers don’t see the full portfolio
- Lost cross-sell opportunities before they even begin
Great reps position holistically:
They frame the company as strategic and comprehensive from day one.
“Hi, I’m Sarah from XYZ Corp. We’re a full-stack IT services partner that helps companies like yours secure, scale, and optimize their entire technology infrastructure. Today, I’m here specifically to discuss how we can strengthen your cybersecurity posture, but I’d love to understand your broader IT roadmap too.”
See the difference?
Sarah just opened the door to multiple conversations.
She positioned credibility across multiple domains while still anchoring her primary offering powerfully.
When the customer faces a new challenge 3 months from now, they’ll think of Sarah’s company — not just for cyber, but for other needs too.
Cross-selling becomes natural, not forced, when the foundation is right.
Why Your Elevator Pitch is Actually Your Cross-Sell Foundation
Here’s the thing about first impressions in sales:
They set boundaries.
And customers buy within the frame you create for them.
If your pitch is narrow, their perception of you is narrow.
If your wallet share is small, it’s because you positioned yourself small from day one.
Think about it like this:
When you meet someone and they introduce themselves as “just a math teacher,” you think of them one way.
But when they say “I’m an educator who helps students build confidence through problem-solving, critical thinking, and creative approaches to mathematics,” you think of them completely differently.
Same person. Same job.
Different frame. Different opportunities.
In B2B complex sales, this matters even more because:
- You’re constantly meeting new people in the organization
- Each person might have heard nothing about you before
- You can’t assume knowledge transfers between stakeholders
- Every encounter is a chance to expand or shrink your positioning
The Real Cost of Getting This Wrong
Let me be honest about something.
Research shows that 86% of B2B buyers don’t see meaningful differences between suppliers.
That’s a huge problem.
If you’re pitching narrow, you’re making it even harder to stand out.
Your cross-sell conversations later in the cycle will feel forced.
Like you’re just trying to “sell more stuff.”
But when you position holistically from the beginning?
Those future conversations feel natural.
Because you already established that you’re a strategic partner, not just a vendor.
The cost?
- Lower wallet share
- Weaker relationship
- More pricing pressure (because you’re a vendor, not a partner)
All of this could’ve been avoided with a better elevator pitch on day one.
Four Questions I Think Every Sales Leader Should Ask
If you lead a sales team, ask yourself these four questions right now:
1. Can your team confidently pitch the company, not just their product line?
Most reps default to their comfort zone — their specific offering.
But can they articulate your full value proposition in 60 seconds?
Try this: Record your reps giving their elevator pitch.
Listen back.
Are they selling a product, or representing a company?
The fix: Train on company-level positioning first, then dive into product specifics.
2. Do they have enough fluency in other offerings to respond credibly?
I’m not asking for expert-level knowledge.
But can your cybersecurity rep handle a basic question about your cloud services?
Can they recognize an opportunity outside their domain?
Can they facilitate a warm introduction to a specialist on your team?
Why it matters: Cross-functional knowledge prevents conversations from hitting dead ends.
“Let me find someone who knows” sounds weak.
“Great question — at a high level, here’s how we approach that, and I’ll connect you with our specialist” sounds like a real partner.
3. Can they handle simple objections outside their domain?
When a customer asks about something your rep doesn’t own, what happens?
Do they freeze?
Do they deflect?
Or do they address it at a high level and follow up with the right person?
The difference: Strategic partner vs. order-taker.
4. Have you truly thought through WIIFM for salespeople AND managers?
WIIFM = What’s In It For Me?
This is where most cross-selling initiatives die.
Your reps won’t push what doesn’t help their quota.
Your managers won’t reinforce what doesn’t help their team numbers.
Hard truth: If your compensation structure doesn’t reward holistic selling, it won’t happen.
Period.
You can’t just tell reps to “cross-sell more.”
You have to make it worth their while.
Otherwise, they’ll keep doing what gets them paid — selling their narrow product line and moving on.
So What Do We Actually Do About This?
I’m not going to give you some complicated framework here.
Just practical things that actually work.
Train for company fluency, not just product expertise
Your reps need to know the full portfolio.
Not as experts in everything.
But fluent enough to have conversations.
Create quick-reference materials.
Build simple frameworks they can use.
Practice the 30-60 second company pitch until it’s natural.
Build credibility bridges
Teach your team to acknowledge other solutions naturally in conversation.
“That’s interesting you mention that challenge — we’ve actually helped clients with similar issues through our cloud infrastructure services.”
Develop warm handoff language so they can bring in specialists smoothly.
Make it easy for them to connect dots for customers.
Make it conversational, not scripted
Nobody wants to hear a sales pitch that sounds like a sales pitch.
Focus on the problems your company solves, not feature lists.
Use everyday language.
Leave room for curiosity and questions.
The goal isn’t to sound polished.
The goal is to sound real.
Final Thoughts: The Strategic Imperative
Cross-selling begins long before the actual cross-sell moment.
It starts in the first 90 seconds of your elevator pitch.
Get positioning right at the beginning, or you’ll struggle with expansion forever.
The investment you need to make:
- Better training programs
- Clearer company-level messaging
- Aligned incentive structures
The payoff:
- Higher wallet share in every account
- Deeper, stickier customer relationships
- Sustainable, predictable growth
So let me ask you this:
How confident are you that your team’s elevator pitch sets the stage for cross-sell success?
If you’re not sure, here’s what I’d recommend:
Audit your team’s elevator pitches this week.
Listen to how they introduce themselves and your company.
Ask yourself: “Does this pitch open doors or close them?”
Because I promise you — your cross-sell success (or failure) has already been decided in those first 90 seconds.
The question is: Are you setting your team up to win?
