Secrets to breaking into enterprise accounts and closing megadeals
Secrets to breaking into enterprise accounts and closing megadeals
Just ask Jamal Reimer—closer of a $56,000,000 Oracle deal (yes, you read that right) and the world's leading expert on megadeals.
After more than 20 years of selling to enterprise companies, Reimer uncovered the winning strategies for how to close the biggest deals of your life in Apollo’s most recent webinar. “I want to save you a decade of trying to figure it out on your own through trial and error, Reimer, founder of Enterprise Sellers, said.
Keep reading to learn how to land meetings with executives, create a pitch that captivates your most important prospects, and seal the deal on your biggest enterprise accounts.
What is enterprise sales?
Enterprise sales is the process of selling high-value products or services to large organizations. Enterprise sales involve solutions with significant business impact, often including multi-year contracts, complex implementations, and many stakeholders.
Compared with smaller deals, these are long-term engagements that require a deep understanding of the customer’s business, challenges, and strategic goals. Success often depends on building solutions that can reshape how large organizations operate.
How enterprise sales differ from SMB and midmarket sales
Selling to a 50-person startup versus a 50,000-person corporation is like playing checkers versus chess. Both are games, but the strategy, complexity, and stakes are worlds apart. Here's how they stack up:
- Sales Cycle: SMB deals can close in days or weeks. Enterprise deals? Think months, or even years. It's a marathon, not a sprint.
- Decision-Makers: In an SMB, you might talk to one or two people. In an enterprise, you're navigating a buying committee of a dozen or more stakeholders from finance, IT, legal, and the business units.
- Deal Size and Complexity: Enterprise contracts are significantly larger and come with custom terms, security reviews, and complex legal hurdles.
- Risk: For an enterprise, a bad purchase decision can cost millions and impact thousands of employees. Your job is to de-risk the decision at every step.
Enterprise sales examples and what makes them successful
Enterprise sales isn't just one thing. It could be selling a new cloud infrastructure platform to a global bank, deploying a new HR software across a national retail chain, or providing a comprehensive cybersecurity solution to a government agency.
What these deals share is a focus on large-scale, mission-critical business problems. The seller presented a business case showing how the solution could drive revenue, reduce costs, or mitigate risk at scale. The focus is on strategic outcomes rather than product features alone.
Break out of the matrix into enterprise sales
What's life like for a run-rate seller?
It's filled with high-volume activity, low-level stakeholders, tiny, time-consuming deals, and small commission checks. While these things can still be a reality for enterprise sellers, enterprise sales often revolve around the opposite—high-level strategy and intentional action.
Reimer points out that individual contributors often have a great chance at success on paper, but the system is gamed to make overperformance nearly impossible. According to him, the only way to break out of the game and get what you want out of your sales career is to think bigger, think bolder, and set your sights on the mega-deal.
“Everything you wanted when you started in sales is on the other side of a single, intentional megadeal,” Reimer says.
Leverage your executives to access decision-makers
Breaking into enterprise accounts is a game of chess.
Success often depends on reaching executive decision-makers early in the process.
"I've never seen a megadeal done without executive sponsorship. There's too much entropy, and midlevel people don't even have the mandate to make big investments," says Reimer.
Executives are the driving force behind any megadeal, and if you can't get to them, your deal is over before it's begun.
You have any executive's contact information now, but like many reps, you might feel intimidated to reach out, like you don't know their language or are not worthy of your time.
One of your best strategies will be to leverage your own executives. Go to them with your book of accounts and ask them for any and all mutual connections and support. They are going to be your golden ticket into the room of C-Suite.
Reimer puts it this way: "Don't walk up the mountain. That takes weeks. Go leverage a helicopter to take you to the top of the mountain in 10 minutes. This is the way of the megadealer—and your executives are your first port of call to be your helicopter."
A Megadeal Premise has three key components:
- Core imperative: What the C-Suite needs to achieve this fiscal year
- Distinctive value proposition: Your company's secret sauce
- C-level insight: An undiscovered or unappreciated reality about their business
You need to show that your distinctive value prop is the better, faster vehicle to get them to their core imperative, using the C-level insight as the rationale behind why a "yes" makes sense.
Work with your execs to think creatively when you reach out to deliver this information.
"Cold email and cold calling are like super highways that are bumper-to-bumper jam packed. We need to get off of those superhighways,” Reimer says. “We need to go to other channels."
In the webinar, Reimer gives examples of:
- Sending greeting cards
- Delivering physical gifts for special occasions (birthdays, anniversaries, etc.)
- And handwriting notes
Thinking outside the box to capture the attention of busy decision-makers will set you apart from the swaths of people banging at their door.
The enterprise sales process: A step-by-step framework
While every deal is unique, most enterprise sales follow a predictable path. Think of it as a roadmap to guide you through the complexity. Here's a simplified look at the stages:
- Account Identification and Research: Pinpoint high-value accounts and dive deep into their business challenges, strategic initiatives, and key players.
- Executive Mapping and Outreach: Identify the entire buying committee, from champions to blockers, and orchestrate a multi-threaded outreach campaign to gain access.
- Collaborative Discovery: Work with multiple stakeholders to build a comprehensive understanding of their pain points and cocreate a vision for the solution.
- Value Proposition and Business Case: Present a tailored solution and a rock-solid business case that proves undeniable ROI to the economic buyer.
- Procurement, Security, and Legal: Navigate the final hurdles with the teams designed to scrutinize every detail of the deal.
- Closing and Expansion: Seal the deal and immediately shift focus to delivering value and identifying new opportunities for growth within the account.
Frequently asked questions about enterprise sales
What is the meaning of enterprise sales?
Enterprise sales means selling high-value, complex products or services to large corporations. It involves long sales cycles, multiple decision-makers, and deals that have a significant impact on the customer's business.
What does an enterprise sales rep do?
An enterprise sales rep is responsible for managing the entire sales process for large accounts. They build relationships with executives, develop complex business cases, navigate procurement and legal, and ultimately close large, strategic deals.
What are enterprise sales examples?
Examples include selling a new CRM platform to a Fortune 500 company, implementing a cloud computing solution for a global logistics firm, or providing a comprehensive cybersecurity package to a major financial institution.
How long does an enterprise sales cycle take?
Enterprise sales cycles are long, typically lasting anywhere from six to 18 months, and sometimes even longer. The length depends on the deal's complexity, cost, and the number of stakeholders involved.
What's the difference between enterprise sales and account management?
Enterprise sales focuses on acquiring new large customers (hunting), while account management focuses on nurturing and growing existing customer relationships (farming) to ensure retention and find expansion opportunities.
This story was produced by Apollo and reviewed and distributed by Stacker.
