How to 10x Deal Size: Enterprise Sales Guide by Ton Dobbe
- B2B SaaS Growth Leader
- Published on August 22, 2024
- Updated on September 13, 2024
Table of Contents
Enterprise sales is like trying to convince your whole family to go vegan at Thanksgiving. You gotta deal with Uncle Bob who loves his turkey, Aunt Sue who’s all about that gravy, and your cousin who thinks tofu is a type of martial art. But if you pull it off, man, you’re eating good for years!
I’ve worn many hats in my career. Sales, marketing, global product strategy. But after ~ 20 years in the corporate world, I knew it was time for a change. In 2017, I took the leap and started my own company. Why? Because I couldn’t sit idly by while watching so many SaaS companies and promising scale-ups struggle in the enterprise software space.
The numbers are staggering. 90% of all SaaS startups fail. But here’s what really keeps me up at night: even 75% of SaaS scale-ups – companies that should have already found their product-market fit – can’t seem to nail their enterprise sales strategy. It’s not just bad, it’s a crisis of potential.
Over the years, I’ve developed a unique methodology. It’s about doing things differently – being REMARKABLE. That’s the key to win better customers, and turning $10,000 customers into $100,000 deals.
In this article, I’m going to walk you through my 9-step approach to win more of the right enterprise sales deals. If you’re ready to leave the world of small left over deals behind and step into the big leagues of enterprise sales, you’re in the right place!
What is enterprise sales?
Enterprise sales is a complex sales process focused on selling high-value products or services to large corporations. It typically involves longer sales cycles, multiple stakeholders, and high Annual Contract Value (ACV). Enterprise sales deals require a more strategic, consultative approach compared to transactional Product-led Growth (PLB) sales models.
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The Impact of Enterprise Sales Model on Revenue
Let’s talk about enterprise sales. But what exactly is it?
Enterprise sales isn’t just about selling to big companies. It’s an art form. It’s about navigating complex organizational structures, winning the heart of multiple stakeholders, and closing high-value, long-term deals. We’re not talking about quick wins. This is the long game.
Why does it matter for SaaS companies? Simple. It gets you out of survival mode. It’s about creating a predictable streamof customer driven funding. It’s about optimal profitability, leverage and creating business resilience.
Think about it. Most Sales-led SaaS companies start in the lower-end of the market. They focus on SMBs, chasing after $2K-$10K ACV (Annual Contract Value) deals. It’s not a bad strategy to begin with. But here’s the problem: for many it’s not sustainable for long-term growth.
Enterprise sales opens up a whole new world of possibilities. It’s kind of like switching from a rowboat to a speedboat. You’re moving faster. You’re covering more ground. You’re making a bigger splash.
But what’s the potential impact on profit? It’s massive.
When you nail enterprise sales, you’re not just adding a few digits to your revenue. You’re multiplying it. Those $10K ACVs? They can turn into $100K, $200K, or even million-dollar ACVs. And it’s not just about the initial sale. Enterprise clients very often bring in upsells and account expansions.
Here’s another thing: enterprise clients tend to stick around longer. They’re not just buying a product; they’re investing in a solution. This means lower churn rates and more predictable revenue streams.
Enterprise sales isn’t easy. It requires a different approach, a different mindset though.
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The 9-Step Enterprise Sales Strategy
So you’re sitting across the CFO of a dream prospect. Your palms are sweaty. Your throat’s dry. You’re about to pitch a deal that could make or break your quarter. Hell, your whole year.
Sound familiar?
I’ve been there with the sales teams at Unit4. More times than I can count. That’s where we cracked the code. Here’s my step-by-step enterprise sales strategy guide:
Step 1: Treat enterprise customers as partners.
You know what’s so wild about this ‘Partner approach’ to enterprise sales? It’s like being a therapist, but instead of helping people with their mental issues, you’re solving their million-dollar problems. And let me tell you, enterprise clients problems are a whole different level of crazy. But if you listen and talk long enough, they might just adopt you… into their budget!
BUT here’s the deal: customers can smell a sales pitch from a mile away. They’re tired of it. I’ve seen it time and time again. The moment you start pushing your product, they shut down. So, what’s the alternative?
Simple. Be a partner, not a sales rep.
This isn’t just semantics. It’s a fundamental shift in how you approach enterprise sales. Instead of focusing on your quota, focus on their needs. It’s a subtle change, but the impact is huge.
I remember working with a SaaS company that was struggling to close big deals. Their pitch was solid, their product was great, but something obviously wasn’t clicking. We dug deeper and realized they were coming at it all wrong. Sales reps were so focused on selling that they forgot to listen to their prospects.
So, we flipped the script.
We started every conversation with simple questions like:
- Tell me about your biggest challenges when it comes to [desired outcome].
- What’s going on in your business that makes [what they shared] a priority?
- What challenges are you facing that you’d regret not solving six months from now?
And you know what? People opened up. They shared their real challenges, their frustrations, their goals.
This approach takes time. It requires patience. You can’t rush trust. But when you invest in building a genuine relationship, the payoff is enormous.
I’ve seen deals triple in size simply because the sales team took the time to understand the customer’s broader business context. They weren’t just selling a product; they were solving a problem.
Remember, in enterprise sales, you’re not just closing a deal. You’re starting a partnership. And partnerships are built on trust, understanding, and mutual benefit.
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Step 2: Care about enterprise customers' money.
Some of these enterprise sales reps, man. You ever see these sales reps who treat the customer’s budget like it’s Monopoly money?
In my years of experience in enterprise sales, I’ve noticed something crucial. The best enterprise sales reps don’t just care about closing deals. They genuinely care about their customer’s financial well-being.
I call this “financial empathy”. It’s about treating your customer’s budget like it’s your own hard-earned cash. Sounds simple, right? But you’d be surprised how few people actually do this.
Start asking questions like:
- How will this investment impact other departments?
- What’s the opportunity cost?
- How does this fit into your long-term financial strategy?
You are having meaningful conversations about value, ROI, and strategic alignment.
This approach doesn’t just help you close deals. It fundamentally changes how decisions are made.
When you show genuine concern for a customer’s finances, you build trust. You become a advisor, not just a vendor. And in the world of enterprise sales, trust is currency.
I’ve seen this play out time and time again. Enterprise deals that seemed dead in the water suddenly spring back to life. Why? Because we showed we cared about more than just making a sale.
Remember, in enterprise sales, you’re not just selling a product. You’re selling a financial decision. A big one. Treat it with the respect it deserves.
Step 3: Dig deep when talking to enterprise buyers.
Ever played the “Why” game with a child? It’s enlightening. And exhausting. But in enterprise sales, it’s the way to go.
In my experience closing enterprise deals, the first answer is RARELY the real answer. Stakeholders will give you surface-level answers. It’s your job to dig deeper. To peel back the layers. To find the real pain points.
So, I developed a little habit. I never settle for the first answer. Or the second. Or even the third. I keep probing until I hit bedrock… or get kicked out of the Zoom call 😀
Here’s how it works:
- Customer says: “We need better reporting.”
- I ask: “Why is that important to you?”
- They respond: “To track performance better.”
- I dig deeper: “What impact would better performance tracking have?”
They finally reveal: “It would help me meet profitability expectations with more consistency.”
Bingo! Now we’re getting somewhere. Not only that but it also opens you a path for you to price your solution more effectively.
But these sales reps who don’t dig deep, man… they’re like archaeologists afraid to get their hands dirty. They see a little bone sticking out of the ground and they’re like, “Look, I found a T-Rex!” Nah, buddy, you found a chicken wing. Keep digging before you embarrass yourself in front of National Geographic… or worse, your sales manager.
Remember: in enterprise sales, the first answer is rarely the whole story. Keep digging. The treasure is often buried deep. Don’t accept the first answer. Keep digging. Keep asking “why?”
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Step 4: Simplify chaos when doing complex sales.
Enterprise environments are messy. Chaotic, even. It’s your job to bring clarity.
Executives are drowning in data. Drowning in options. Paralyzed by complexity. Sound familiar?
Here’s the secret: simplify. Cut through the noise. Simplify the chaos by focusing on the essence.
Take a step back. Ask the client simple questions like: “What’s costing you the most money right now?” Help them prioritize what pain hurts them most and in what context.
Context is king. A critical issue for one department might be trivial for another. You need to prioritize pain points within the larger organizational context.
I use a simple matrix:
- Urgency: How soon does this need to be addressed?
- Impact: How much does this affect the bottom line?
- Scope: How many departments or processes does this touch?
This approach works wonders. It helps customers see the forest for the trees. It gives them a clear path forward.
I once helped a client reduce their “must-have” feature list from 50 items to just 7; resulting in faster implementation, quicker ROI, and a much happier customer.
Remember: your job isn’t to solve every problem. It’s to solve the RIGHT problems. The ones that matter most.
In the chaos of enterprise needs, be the voice of clarity. Simplify. Prioritize. Focus.
That’s how you turn confusion into conversion. That’s how you close big enterprise deals.
Step 5: Paint the big picture for enterprise clients.
Let’s talk about perspective. In enterprise sales, it’s everything.
I’ve seen countless enterprise deals fall apart because the salesperson couldn’t paint the big picture. They focused on features, not outcomes. On products, not solutions.
Here’s the truth: your enterprise client isn’t just buying software. They’re buying a vision.
I remember sitting in a sales meeting with a CFO of a large consulting organization in Philadelphia. Our product demo was pretty good. But I could see I was losing him.
Then it hit me. I connected the demo to a story from another customer we had in Europe and connected the dots how it had helped their CFO meet their personal KPIs with consistency.
So, I flipped the script. We weren’t talking about software anymore. We were discussing his career goals, his department’s objectives, the company’s strategic direction.
This is how you create the big picture for enterprise clients. Connect the dots. Personal goals. Department targets. Company vision. Your solution.
This will help your prospect sell this vision internally. They need ammunition for boardroom battles. Data for decision-makers.
So, I always ask: “Who else needs to buy into this?” Then we give our champion the right arguments. The right sales collateral. The right numbers. The right story.
Remember: in enterprise sales, you’re not just convincing one person. You’re enabling THEM to convince OTHER decision makers. You’re crafting a narrative that resonates across the organization.
Paint the big picture. Connect the dots. Arm your product champions. That’s how you close big enterprise deals.
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Step 6: Emphasize the cost of inaction to shorten longer sales cycles.
Inaction is expensive. It’s a silent killer of businesses. But here’s the problem: it’s comfortable.
I’ve seen it too many times. Enterprise client knows they need to change. They’re excited about your solution. But then… nothing. They hesitate. They delay. They stick with the status quo.
Why? Because change is hard. It’s risky. It’s easier to do nothing.
This can be because of two things:
- Value and Criticality are not perceived high enough.
- All of that is clear – but they just fear messing up.
So your job is to make your solution the least risky option.
If it’s 1, instead of just showcasing benefits, I recommend you highlight the cost of inaction. Put things in perspective:
- “What happens if you don’t solve this problem this year?”
- “How much is this issue costing you every month you delay?”
- “Where will your competitors be if you don’t act now?”
Now, customers are selling themselves on the urgency of your solution.
But here’s the key: you’re not fear-mongering. No, no, no. You’re simply showing the reality! You’re helping customers see the full picture.
Remember: in enterprise sales, your biggest competitor isn’t another company. It’s inertia. It’s the allure of “business as usual”.
So your mission here is to make “usual” uncomfortable. Make change feel safer than stagnation. Make inaction expensive. Make change irresistible. And watch your enterprise sales soar.
If it’s 2, so value and criticality are clear, but they’re just scared to make the bet, I recommend showcasing empathy and address their objections right away.
- “Can you help me understand the steps your company needs to take to make a confident yes/no decision?”
- “What specific concerns or risks are making you hesitant to move forward?”
- “Who are the key stakeholders that need to be involved in each step, and what do they care about most?”
- “What would make you feel fully confident that implementing our solution is the right decision for your business – and for you personally?”
Step 7: Deliver concrete proof of value to multiple stakeholders.
Demos are dead. There, I said it!
In my early days, I lived and died by the demo. I’d spend hours showcasing every feature. But you know what? It rarely moved the needle on enterprise deals.
Here’s why: enterprise buyers don’t want features. They want proof of a solution. Concrete, irrefutable evidence that you can solve their specific problems.
So, I changed my approach. I stopped demoing and started proving.
How? By solving real problems right in front of their eyes.
I remember one meeting. Instead of a presentation, I brought my laptop. I asked multiple stakeholders to share their most pressing issue. Then, right there, I used our software to solve it.
We’d just saved them weeks of work in minutes. I closed the deal that same day.
That’s the power of concrete proof. It’s not about that your product ‘can do this or can do that’. It’s about what it can do for them.
Remember: in enterprise sales, seeing isn’t believing. Experiencing is.
Don’t show them features. Prove its value. Make it real.
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Step 8: Exceed expectations.
Doubt is a deal-killer. It lurks in the minds of decision-makers, whispering, “Will this really work for us?”
Obliterate doubt. Crush it. Leave no room for second-guessing.
How? By over-delivering. By solving problems in a way others cannot.
It’s not about showing off. It’s about demonstrating superior problem-solving. Proving you’re not just another vendor, but a partner in their success.
Take their toughest challenge. The one no other solution has cracked. Dig deep. Leverage every resource at your disposal.
Don’t just present a solution. Bring it alive. Solve their most intractable problem right before their eyes – in the shortest amount of time, even if that’s 10 seconds.
This approach doesn’t just eliminate doubt. It creates excitement.
Show initiative. Think like a stakeholder, not a typical sales reps.
In enterprise sales, good enough isn’t good enough. You need to be exceptional. Remarkable. Unforgettable.
That’s how you eliminate doubt. That’s how you build unshakeable confidence. That’s how you close enterprise deals that transform businesses – yours and theirs.
Remember: in enterprise sales, the extraordinary becomes the expected. So always ask yourself, “How can I go one step further?”
Step 9: Guide the purchase decision.
The art of guidance. It’s subtle. Powerful. And often misunderstood by enterprise sales reps.
In enterprise sales, you’re not just closing a deal. You’re steering a ship. A big one. With lots and lots of stakeholders.
Here’s the secret: don’t sell your product. Guide the customer to make the best possible buying decision.
I’ve seen too many sales reps drone on about features. Speeds and feeds. Bells and whistles. It’s a trap. Don’t fall for it.
Instead, steer every conversation towards valuable problem-solving. Ask questions around three simple categories:
- What’s the situation?
- What’s changing?
- What’s most challenging?
Asking questions around these areas shift the focus. From your product to their outcomes.
It’s a mindset change. You’re not a vendor pushing a solution. You’re a consultant uncovering opportunities.
Think bigger. Broader. What’s the ripple effect of solving their problem? How does it impact other departments? The entire organization?
Paint a vivid picture of success. Not in terms of your product’s capabilities. But in terms of their achieved goals. Their realized ambitions.
Remember: customers don’t buy products. They buy better versions of themselves. Of their companies.
Guide them to that vision. Show them the path. Be their navigator in a sea of options.
This approach transforms the purchase decision. It’s no longer about choosing a product. It’s about choosing a future.
That’s how you close enterprise deals. That’s how you turn $10K customers into $100K partners.
Guide. Don’t push. Solve. Make them buy.
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Key Principles for Success in Enterprise Sales
Want to win big in enterprise sales? Forget everything you’ve been taught. SaaS sales teams following the same old playbook are like lemmings in suits. “Let’s all jump off the cold-call cliff together!”
Following the crowd leads to mediocrity.
I’ve seen it time and time again. SaaS sales teams following the same old playbook. Cold calls. Generic pitches. Feature comparisons. It’s a race to the bottom.
Take a different path. Do the opposite.
Instead of cold calling, built relationships. Rather than pitching, listen. Focus on solving problems, not selling products.
But differentiation isn’t enough. You need to be remarkable. In every interaction. Every proposal. Every follow-up.
What does remarkable look like? It’s doing the unexpected. It’s surprising your prospects with insights they’ve never considered. It’s delivering value before they’ve even signed a contract.
I once turned a standard proposal into a mini business plan for a prospect. The client looked at me like I’d just pulled a rabbit out of a hat. “Is this… actual value?” “Yes, sir, and for my next trick, I’ll make your competition disappear!” They were blown away. We closed the deal.
Remember: in a sea of sameness, the standout always wins.
So, ask yourself: What can I do differently? How can I surprise my prospects? What would make them say, “Wow, I’ve never seen that before”?
That’s how you do enterprise sales. Be different. Be remarkable. Be uncomparable.
It’s not easy. It takes courage. Creativity. Commitment. But the payoff? Enormous.
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Conclusion
Let’s recap my enterprise sales strategy:
- Be a partner, not just a sales rep.
- Care about your customer’s money like it’s your own.
- Dig deeper to uncover root causes.
- Simplify the chaos.
- Paint the big picture.
- Emphasize the cost of inaction.
- Deliver concrete proof of value.
- Exceed expectations at every turn.
- Guide the purchase decision.
Think about the potential impact on your career. Bigger deals. Higher commissions. Faster growth. More recognition. You could become the go-to person for those big enterprise contracts.
So, here’s my challenge to you: Implement this approach. Start today. Pick one step. Apply it to your next sales call. Then another. And another.
It won’t be easy. You’ll face resistance. Old habits die hard. But persist. The rewards are worth it.
If you have any questions or need help how to stand out in your market, don’t hesitate to message me on LinkedIn. I’m always happy to help!
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FAQs
How long is a typical enterprise sales cycle?
Enterprise sales cycles can vary greatly, but they’re often longer than transactional sales models like PLG. Typically, enterprise sales cycles last 6 to 18 months. This extended timeframe is due to the complexity of the deals, involvement of multiple stakeholders, and the need for thorough evaluation of custom solutions.
What's the difference between enterprise sales and transactional sales?
Enterprise sales involve complex, high-value deals with mid-sized to large corporations, often stretching across multiple departments and involving multiple decision makers. Transactional sales, on the other hand, are simpler, shorter sales cycles typically involving individual prosumers or small businesses, with standardized products and fewer stakeholders.
How important is social proof in enterprise sales?
Social proof is crucial in enterprise sales. Enterprise buyers often seek reassurance through case studies, testimonials, and references from large companies. This helps mitigate perceived risks associated with significant investments. Sales reps should leverage success stories and testimonials to build credibility.
What are some common challenges in enterprise sales?
Common challenges in enterprise sales include navigating longer sales cycles, engaging multiple stakeholders, addressing complex needs and managing higher risks. Sales reps face difficulties in maintaining sales momentum throughout the process, coordinating with decision makers and adapting to changing requirements.
What metrics should sales leaders focus on in enterprise sales?
Key metrics for enterprise sales include average deal size, sales cycle length, win rate, and customer lifetime value. Sales leaders should also track engagement with multiple stakeholders, pipeline velocity, and the effectiveness of different stages in the sales process. ROI and implementation success are crucial long-term metrics.
About the Author
Ton Dobbe is a seasoned expert in B2B enterprise sales and SaaS growth. With 20 years of experience leading global product marketing and strategy, Ton has a unique approach to helping SaaS companies achieve predictable traction. Ton is on a mission to reduce the high failure rate among B2B SaaS companies. His proven methodologies, like the Traction Foundation Pressure Cooker and the Traction Momentum Habit-Changing Program, empower B2B SaaS companies to stand out in their market, attract the right customers, and build lasting success.
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