Enterprise sales are super tough.
These sales have a success rate of only 10% to 30%, and they demand a lot of effort with no guaranteed return. Navigating them can feel like literally dealing with a black box. You are often in the dark about how the company operates, who the key decision-makers are, and whether they even want your solution.
Over the years, at Roar Global, we have built a ton of experience in enterprise sales. (Read more about our recent acquisition of Creator Flow). We’ve been fortunate enough to land contracts worth millions, but we’ve also spent years chasing deals that yielded a grand total of $0.
This guide breaks down how we approach and execute enterprise sales at Roar. It’s not the only way to do things, nor is it the ultimate standard, but it’s what has worked for us.
What We Consider Enterprise Sales
First, it’s important to define what an enterprise sale is and how it differs from smaller transactions.
For us, an enterprise sale is any potential contract worth over $200K per year. While these deals often involve large, established companies, size isn’t the only factor. The key is targeting companies with the budget and long-term means to support such a contract.
Enterprise sales also involves long sales cycles, managing multiple stakeholders, and navigating complex decision-making processes.
This guide focuses on outbound sales and isn’t meant for converting inbound enterprise leads (if you’re lucky enough to have those)!
The Reality of Enterprise Sales
Outbound enterprise sales require a fine balance between persistence, being proactive, and patience, coupled with a lot of planning.
If you’re a growth company, you can realistically handle only a few enterprise sales opportunities at any given time. These deals are incredibly time-intensive and often need the involvement of sales leadership or founders to close.
The stakes are high, and the process can be gruelling, but the rewards can be transformative for your business.
So, how do you approach it?
Start the process of shortlisting the companies you want to target. You should not only find the biggest or most popular company; but work towards identifying the right enterprise that will find your solution the most useful. Dive into their pain points, strategic goals, and industry trends. Know precisely what solution you’re offering, how it will benefit them, and, most importantly, who your competition is — both direct and indirect.
Good planning here will help you zero in on the enterprises where you can make the biggest impact.
Pro Tip: Don’t start with the Fortune 500s. They’re tough to break into and often have slower decision-making processes. Instead, focus on tier 2 and 3 enterprises that might need your solution. You’d be surprised by how many large companies with 1000+ employees fly under the radar. They often have more accessible decision makers, faster processes, and are more open to new solutions.
Next, identify the top 3 to 5 people within the enterprise who NEED your product or service. These are usually the end users or those who will directly benefit from your solution.
Then, identify the top 3 to 5 people who MAKE the purchase decisions. These individuals are typically in senior leadership roles, such as VPs, procurement officers, or finance directors, who have the authority to approve budgets and sign contracts.
Pro Tip: Reaching out to ex-employees of the organization you’re targeting can give you some great insider information. Ask them for advice on the org structure, internal dynamics, and the solutions already in use. Since you are not selling to these ex-employees, they are often more open to sharing useful insights.
Once you’ve identified your list of 6 to 10 key individuals, start building top-of-mind awareness for your company and solutions. Connect with them on LinkedIn, engage with their posts, attend events they might attend, and target them with ads. The goal is to ensure they recognize your name and associate it with value before you make your first direct contact.
Pro tip: Use LinkedIn's Contact Targeting feature to directly serve ads to key individuals.
The best way to make first contact is through mutual introductions. An introduction from a mutual connection is far more credible than a cold outreach, and your chances of securing a meeting are much higher.
If you don’t have a mutual connection, reach out cold via LinkedIn, introduce yourself, and request a meeting. Follow up with an email if you don’t get a response within a few days. Persistence is key, but balance it with respect and avoid coming across as spammy or desperate.
If you land a meeting, congratulations!!
You should always aim for an in-person meeting. In person meetings are less transactional, and it helps build trust far more effectively than virtual ones.
This might mean you’ll need to travel but don’t make the trip just for this one meeting. It’s smarter to combine it with other meetings, events, or conferences. Plus, it eases the pressure on the person you’re meeting; they’ll be more comfortable knowing you’re not travelling solely for them, especially early in the sales cycle when things are still developing and they do not want to commit.
Pro Tip: Always aim to meet at their offices rather than a coffee shop. An office setting gives you a feel for their culture and keeps things business-focused.
During the meeting, deliver a clear and engaging presentation. Demo your product or service, highlight the value it brings, and make it crystal clear how you stand out from the competition—show them exactly why they should choose you.
After the meeting, keep the momentum alive with a prompt follow-up email. Thank them for their time, attach the presentation deck, recap key discussion points, and clearly outline the next steps.
If the meeting went well, aim to lock in a date for the next meeting with more stakeholders.
If interest seemed low, explore whether there’s room to tweak or customize your offering. If not, step back respectfully but keep the relationship warm—a 'no' today can easily turn into a 'yes' tomorrow.
If you don’t get a response, continue to follow up respectfully. A follow-up every two weeks is perfectly acceptable.
Pro Tip: People are often too polite to say no outright, even if they aren’t interested or know it won’t work out. Learn to read between the lines and understand where you truly stand and then act accordingly.
If things progress - you don’t always need to reach out directly to the decision-makers (the MAKE group). If the NEED group is convinced, the process often organically flows to the decision makers, who may request a meeting or more information. The top-of-mind awareness in Step #3 starts to pay off here, as these decision-makers should, at this point, recognize you and your company
Once the NEED group is on board, work closely with them to navigate the internal approval process. They can become your champions, advocating for your solution within the company.
Whether you win the contract or not, keep building relationships. If you get a 'yes'..that's great! Continue nurturing that partnership.
If it’s a 'no' - stay in touch anyway. These relationships can lead to future opportunities—someone might move to another company where they can recommend you or a project might pivot in a way that makes your solution relevant.
Pro Tip: Use a CRM to track interactions and set reminders for check-ins, coffee catch-ups, or a simple "Hello..how are you doing" WhatsApp message. Stay present without being intrusive.
Enterprise sales are tough, and the industry norm is a 10% to 30% success rate. These sales require significant time, money, and energy. You might make long trips multiple times, and you’ll often hear 'no' or, worse, nothing at all.
But with persistence, consistent effort, and relationship building, a 'yes' is always within reach. Securing an enterprise contract can transform your business, making the journey totally worth it.
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