Ryan Walsh’s Post

It has been my experience that many sellers view "enterprise sales" as the top of the sales profession. Having done both, when I discuss next steps in a sellers career my coaching centers on "What are your internal drivers?" What fuels you - making a sale once a week, once a month, once a quarter, once a year. Do you prefer big commission checks or consistent commission checks? Do you like to have greater control of your sales process or do you want to conduct an orchestra of resources. Then I offer my favorite analogy...Do you want to be a Tuna Boat Captain (big boat, big cost, fighting a huge fish for a long time that sometimes breaks the line right at the boat) or do you want to be a bass fisherman (more places to fish, less expensive gear, more action) Both the Tuna Boat Captain and the Bassmaster can make good money. Choose the one that fuels your personal fire.

Hard closing doesn’t work in Enterprise sales. Here’s why: The person you’re working with, your “champion,” usually isn’t the final decision-maker. Big deals often need approval from the CEO, CFO, or a group of people. There are many steps and reviews, even after your champion says yes. If you push too hard to close the deal, you might damage your relationship with your champion and lose the deal. In Enterprise sales, your job isn’t to pressure them. It’s to guide and help them through their own buying process. You need to understand their timeline, approval steps, and key decisions so you can work together. Help your champion by giving them the tools they need, like business plans, future strategies, and summaries, to sell the idea internally. If you do all of this, closing the deal will be the easiest part. Btw, my partner Steph and I have spent over 300 hours creating a 5-step guide with free templates to help founders and sales professionals improve their sales by attracting ideal clients. If you’d like the free guide, feel free to DM us!

I bet you really don’t know what enterprise sales truly is… “Oh it’s where I can go and close huge deals and make a ton of money!”  Not so fast.  Many organizations have a named ‘enterprise’ sales team, but they’re really not doing enterprise sales. That’s ok, nothing wrong with that, it’s really just nomenclature. Couple things about enterprise sales: **Many stakeholders will be involved on the buyer’s side - the seller will need to manage them all **There’s typically a very heavy implementation consideration or lift for the buyer’s organization **The account may need to be worked for several years including meetings, calls, etc, before even getting into a buying cycle **When you think you’re close, procurement will get involved (you need to be way ahead of that) **If there’s any type of security certification, compliance need, the selling org will need to have passed it or have it **Multiple groups within the selling organization will need to be involved to support the deal (not just an AE + SE/SC) Below we’ve taken a look at the sales cycle lengths and average deal size data for a few dozen ‘enterprise’ teams, and broken them down into a few buckets. 1 / Traditional enterprise - yes, this fits the mold. 2 / Getting there - note the deals take a long time but aren’t as big.  Ideally the deal sizes will continue to grow, as will the efficiency by default 3 / Not truly enterprise - these are very good transactions for these companies, but typically wouldn’t have all the requirements and bells / whistles of a true enterprise deal (plus they’re smaller and will move faster) We collect this data from over 150,000 b2b sellers globally across 25,000 organizations. *** ✅ Oh and by the way you can see what these enterprise sellers are earning as well: https://bit.ly/45kqnHi

Sales Engineer / AE - “Question of the Day” for Thursday Oct. 31, 2024. How do we sell? What is the absolute best mindset to be in for enterprise sales? I had scheduled a closing call with a large trading firm that involved their CTO, my manager and myself. As we sat down, a fourth person entered the room. It was the CFO. CFOs don’t show up for sales calls for the fun of it. They’re there for a reason. The reason is, they’re the ones writing the check. They’re the ones who are responsible for the sustainability of the entire business. That’s why they’re there, to ensure that money is spent wisely so that the business can stay in business. It was 10 days before the end of the quarter. We were set to deliver a large cadre of enterprise servers which they desperately needed. We were there to ink a seven figure deal. The CTO had given us the green light. I had it forecasted at 90% to win for the quarter. The CTO and I were in alignment. The CFO and I were not. He hadn’t finished fully depreciating the equipment he already paid for. It didn’t matter how competitive we were technologically or how low our cost, he couldn’t write a check at this time. His responsibility to the balance sheet wouldn’t allow it. Seeking Alignment is the best mindset to be in for enterprise sales. Are you in alignment with the person writing the check for your deals? Don’t get Spooked by not knowing where and when the funding is coming from on your deals. Ask. Happy Selling!

I talked to an 'enterprise salesperson' last week that told me his company changes the sales territories every year. It’s one of the dumbest things a company can do. A true enterprise sale often takes 18-36 months. By playing musical chairs with nominated accounts, they are going to yank the salesperson out of the territory just as they are getting traction... ...and give the opportunity to someone new that the prospect doesn't know or trust. If there are any Execs of SaaS vendors out there, please PLEASE don't allow this to happen. You're just sabotaging your own success. Create a key account plan, identify any traction within the account, provide support where needed and BE PATIENT. There are ways to measure early traction beyond hard revenue. If you can't hold your nerve longer than 6 months, then you shouldn't be trying to do enterprise sales in the first place. Am I wrong?

As a newbie in tech sales, you might have across the word “enterprise sales” and think, “oh what is this and I don’t think I am qualified” This me telling you not to mind it as it is one of those corporate jargon. It’s the same thing you’re currently doing but you’re just selling to big companies. Enterprise sales refers to the process of selling products or services to large organizations, often referred to as enterprises. These sales typically involve complex sales cycles, high-value contracts, and multi-departmental decision-making. Enterprise sales are common in industries like technology, software (especially SaaS), and consulting. Key Characteristics of Enterprise Sales: 1. High Deal Value: Enterprise sales deals are often large and involve significant financial investments. 2. Long Sales Cycles: The sales process can take months or even years due to the complexity of the organization and the need for multiple approvals. 3. Multiple Stakeholders: Decisions are rarely made by a single person. Instead, it involves various departments like IT, finance, procurement, and executives. 4. Tailored Solutions: Products or services are often customized to meet the specific needs of the enterprise client. 5. High Risk/Reward: While enterprise sales can be lucrative, the stakes are higher as the loss of a deal can significantly impact revenue projections. Skills Required for Enterprise Sales: • Relationship Building: Establishing trust with multiple stakeholders over time. • Strategic Selling: Identifying key decision-makers, understanding organizational needs, and aligning solutions to those needs. • Negotiation Skills: Handling complex contracts and securing win-win agreements. • Industry Expertise: Understanding the client’s industry to provide relevant insights and solutions. • Persistence and Patience: Managing long and often uncertain sales cycles. Examples: • A SaaS company selling a company-wide CRM solution to a big company like Dangote or those companies doing a minimum of half a billion yearly etc. • A consulting firm securing a multi-year strategy implementation contract with a government agency. Enterprise sales differs from SMB (Small and Medium Business) sales in its scale, complexity, and approach. It often requires more resources and a highly skilled sales team to execute effectively. So basically they just want you to have the capability to understand office politics, ability to negotiate very large deals like $50,000 and above (NGN80m or NGN100 million and above) etc You get the point, yea?

What is Enterprise sales? How does it differ from SMB sales? How is it different from Mid-Market sales? What skills are needed? What approaches are required? What kind of leaders are required? As Enterprise sales is likely the most overused job title on LinkedIn, and many sales leaders have no background in enterprise sales, a refresher from HubSpot is welcome to educate and to remove any confusion that might still exist. This level of sale is only for those salespeople and sales leaders who have direct enterprise sales experience.

The 5 Biggest Lies Companies Tell Themselves About Enterprise Sales Enterprise sales is no walk in the park. Yet many companies think they can just point their sales team at bigger accounts and watch the deals roll in. They tell themselves lies that set their teams up for failure. Let's look at the 5 biggest fantasies companies cling to when moving from SMB to enterprise sales. First, the mother of all lies: "Keep everything the same, just aim reps at bigger accounts." Might as well ask pier fishermen to toss their poles and go harpoon a whale! Next, "Our reps can handle enterprise clients." Maybe...but usually not. SMBs are smaller, more agile. Fewer layers of management. Easier executive access. Faster decisions with fewer people. The CEO of a company I advise offered bigger accounts to his account managers. One wanted only inbound leads. Another took the accounts but used the same approach, only closing small deals. Learning enterprise sales takes time and experience. SMB reps can make the switch in a couple quarters. Most take much longer. Another whopper: "Reps can just pick up enterprise selling." Wrong. Without guidance, they'll get lost in the forest. They won't know how to prospect. Or navigate complex decision-making. Or handle corporate politics. Or craft a compelling value story. You have to show them. Next, "More activity will drive bigger deals." Sure, and pedalling your bike faster means you can race Formula 1. Finally, "We can sell the same product to the Fortune 500." Maybe your features are solid, but you'll get blindsided by enterprise requirements around reporting, compliance and security. Reps sell the dream then fail to close when requirements surface. Wasted cycles. The truth? Enterprise sales is totally different. A different motion, mindset, tools. Redirecting your SMB team will fail. And you'll lose your best reps when the reality hits. Moral: Don't buy the lies. Enterprise sales needs a custom approach to succeed.

In enterprise sales, you have to close the deal before closing the deal. Or be ready to lose your shirt.. The last enterprise deal I sold was a 3-year, $5M deal.  The two deals before that one, didn’t work out as well. One lost; and one we had to drop our pants on pricing (wet foolishly called it a loss leader to appease ourselves). The difference?  Positioning, collaboration, and structured communication with the right people long before presenting to decision makers. Enterprise sales aren’t like other deals. The stakes are higher, the cycles are longer, and the biggest mistake you can make is walking into a proposal meeting thinking you’re there to close. 𝗧𝗵𝗲 𝗿𝗲𝗮𝗹 𝗽𝗿𝗼𝗯𝗹𝗲𝗺? 🥊 Most technical founders rely on a passive selling process, presenting a solution and pricing without first securing buy-in on value and ROI. The result? Pushback on pricing, drawn-out negotiations, or a flat-out "no." 𝗦𝗶𝗱𝗲𝗯𝗮𝗿 — 𝗧𝗵𝗲 𝗼𝘁𝗵𝗲𝗿 𝗽𝗿𝗼𝗯𝗹𝗲𝗺?: There you were thinking that deep pockets meant pricing would be easy. Sound familiar? Here’s the shift 💡: Enterprise sales are won through collaboration long before the final meeting. You need to close the deal before you formally close the deal. Here’s how: 1/ Work with internal champions. ↳ Identify influencers or contacts who can advocate for your solution. Collaborate with them to understand decision-makers’ priorities. 2/ Define ROI early.
 ↳ Before you even mention pricing, tie your solution to the enterprise’s core challenges. What’s the measurable impact? Revenue saved? Risk reduced? 3/ Get aligned on value.
 ↳ Make pricing secondary to the decision by building consensus around the problem you’re solving and the outcomes your solution delivers.. Enterprise clients don’t just want to buy—they want to believe. They want a partner, not a vendor.  Go deep on value and ROI, collaborate on the approach, know the who’s and how’s, and close before closing by the time you walk into that final meeting, the deal is done. Need help on strategic enterprise selling?  Let's talk. Hope this helps. ------------------------- You built the product.  I help build the business.

Not everyone wants to build an elite sales team. I received an email this morning from a prospective customer at a large enterprise SaaS company. This company has a sales leader who is selling Databook as good as our best rep. She is Championing us because she's been able to describe, in her language, how Databook has already paid for itself and can drive significant further ROI in her organization. She is an elite seller who has staked her reputation and political capital because she truly wants her company to become an elite sales organization. But not everyone is on the same page as her yet, and it's taken ~6 months for her to convince multiple stakeholders in the org to buy into her vision. This is one of the reasons why enterprise sales are complex and can take 6-9 months. I can almost guarantee this seller is going to be VERY successful wherever she works and I look forward to supporting her current organization similar to our other Champions who are building elite sales teams at Databricks, Celonis, Microsoft, and Salesforce, to name a few. I commend her for wanting better for her organization and dragging her team into the next level of executive selling. Not everyone wants that or is willing to fight for it. She understands that the old way of selling doesn't work anymore with product demos of speeds and feeds and quoting and hoping. She's a top seller, and I can't wait to partner with her to help her realize her goals and drive faster, bigger outcomes for her customers. 🚀 Have a look at the image here and see if your team is consistently operating at Level 4 or 5?