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How To Prospect Enterprise Accounts from a Cold Start

One of the most difficult jobs in SaaS sales is selling to companies large enough to have their own postal codes. Declaring account opening as the most difficult part of this process is a reasonable claim given there are no existing relationships that can be leveraged for introductions to key stakeholders. The given is a very important note because getting a proverbial foot in the door through a common connection trumps any kind of cold outbound. The purpose of this article is to outline a strategy for penetrating a set of enterprise accounts when no referrals are possible. Some of this content will be applicable to a variety of selling scenarios, but the focus will be on a “short list of large accounts” scenario.
Patrick William Joyce (PWJ)

One of the most difficult jobs in SaaS sales is selling to companies large enough to have their own postal codes. Declaring account opening as the most difficult part of this process is a reasonable claim given there are no existing relationships that can be leveraged for introductions to key stakeholders. The given is a very important note because getting a proverbial foot in the door through a common connection trumps any kind of cold outbound. The purpose of this article is to outline a strategy for penetrating a set of enterprise accounts when no referrals are possible. Some of this content will be applicable to a variety of selling scenarios, but the focus will be on a “short list of large accounts” scenario.

Researching Current Customers + Competition

“If you know both yourself and your enemy, you can win 100 battles without a single loss” – Sun Tzu, Art of War

When I’m trying to figure out the top of the sales funnel, analyzing what’s happening at the bottom of the funnel is the first order of business. The main questions on my mind are: 

  • Why did the last 5 deals close? 
  • What pushed those deals over the line?
  • What do the customers sound like when they talk about the workflow you intend to impact?
  • What are the downstream business outcomes you are unlocking with this software?
  • What are the problems with the current workflow?
  • How is the customer solving this right now?
  • Internally or using other vendors?

It is surprising that these questions are often unanswered while the company is trying to build an outbound sales motion. There’s nothing about the feature set of the product you’re trying to sell that will entice a decision maker at one of your key accounts to take a meeting with you and try to figure out how they might use it. You need a deep understanding of the workflow you intend to impact and what your competition is – whether you’re competing against a home-grown internal customized solution or another vendor is important information. In all likelihood, you’ll run into both. We’re spending this time up front because this knowledge is what you will lead with at the top of the funnel reaching out to potential customers. The bottom of the funnel informs the top of the funnel in a cyclical, repeatable pattern. 

I’ve made a habit out of creating diagrams that show where the product I’m selling sits in the competitive landscape. Usually these are 3-circle Venn diagrams, a strategy I learned from Justin Michael (author of Tech-Powered Sales). Here’s an example:

The purpose of this exercise is twofold; it will solidify your understanding of the competition and serve as a compelling visual when prospecting and trying to spark interest. More can be found on creating these diagrams here. Starting by creating these diagrams has worked for me, but this step is optional. It does give you a compelling visual to use, however, I’ve also had success with using some other type of visual. There’s more detail to the visual prospecting strategy you can find in the following sections. 

The most important preparation steps are understanding the problems you are solving already, why people buy, and what else they might be doing to solve their problems without you. One of the reasons this is so important is because at an enterprise-level account, it is safe to assume the organization is at a maturity level where most, if not all, potential bottlenecks in runtime-essential business operations have been identified and resolved with some level of competency. Showing an understanding of their problems and probable solutions will do wonders for the efficiency of your outreach efforts. The more you know, the less you need to say, and the better your outcome will be. 

Persona Based Messaging

There are dozens of potential stakeholders who own the business outcomes you intend to impact in any enterprise-level account. Depending on the company, product, and problem, there could even be hundreds of people with whom you could have meaningful conversations. Understanding each persona and what their workflow is like is an essential part of account penetration. One must be able to navigate the different tasks in the workflow in order to start matching people with their roles. A great resource for this mapping exercise is the company job board. HR will likely use internal language in the job postings, which gives access to key information about the job functions for each title. This is key information for those selling complex products that impact more than one business unit. Even if this is not the case, there’s a flanking strategy that could be employed. It is still valuable to understand as much as you can about who does what in each account. 

Given the lack of access to information about what each title is directly responsible for and the difficulty of navigating and mapping an account from the outside, it is imperative that the sales rep think creatively about how to get an edge. Starting at the top and working down toward the CEO of the problem (who is usually not the actual CEO) is a common strategy and is completely valid. If a C-level executive forwards your email, you’re probably getting the meeting with the VP. Likewise, if a director or manager gets nudged to screen you by their superior, the likelihood of setting a meeting is high. We must also gather knowledge from the bottom and work our way up at the same time. Call into the sales line. Message other sales reps who work for the company and ask for help. This works. Armed with that information, the potential for a conversation with someone even one step closer to a decision maker has a higher chance of having an impact if you can mention your chat with Bob Smith. At the highest level, your account penetration effort can uncover problems the executive team didn’t even know they had, therefore unable to solve, until you arrived.

A messaging strategy should be thought out well in advance so when it comes to game time, all you have to do is execute. There are three very specific layers of personalization to leverage:

  1. Common connections 
  1. (give your CEO a seat on Sales Navigator for TeamLink and mine their first and second degree connections)
  1. Prospect’s work history compared to your client list 
  1. (“Noticed your time at Acme, we help them do X - was hoping to go over some similar ideas for Gammacorp” – this sets!)
  2. Look for prospects that have changed roles in the last 30 days since new jobs and promotions usually come with a desire to shake things up and a freshly unlocked budget
  1. Prospect-authored content
  1. If they post on Linkedin, use it. If they are on podcasts, use it. If they’re quoted in Forbes, use it.

 

The 1:1 personalization is not a good reason for a prospect to meet with you. The idea is to avoid forcing a bit of personalization that lacks relevance. You might come across prospects who will answer you because they liked the amount of effort you put into getting their attention, but this does not mean they will allocate resources toward your solution. Focusing the messaging around the potential business problems you can solve and outcomes others have achieved with your software will improve your positive results as those meetings turn into demonstrations and the deal progresses through the sales stages. 

C-level executives are thinking about a vision for the future and making decisions they feel will have a downstream impact for the next 3-5 years. VP level executives are usually trying to make decisions that will have an impact in the next 3-6 months, while their Director and Manager-level subordinates are trying to make an impact immediately in order to get promoted or leverage the results they were able to achieve for a better title elsewhere. Of course, this is a broad generalization, but important to start thinking about as you develop messaging for each persona. Think bi-directionally in terms of job function and seniority. Your messaging matrix might go after Sales, Marketing, and Revops with C-level, VP, and Director titles in each. The outcomes you’re driving toward will likely differ by seniority and the messaging should be tailored to each contact’s likely workflow. 

This is persona-based differentiation and is very efficient since most of the work is done up front. Though you might come back and tweak as you’re going along, it drastically reduces the amount of time spent trying to personalize each time a message is sent.

List Building and Targeting Tactics

For each account being targeted, there should be a corresponding list in LinkedIn Sales Navigator. Getting slick with Boolean operators (AND, OR, NOT) in keyword searches leveraging the internal language pulled from the job description research will make filtering the many thousands of employees in each account easier. There should be at least 30 contacts saved in each list to focus on. Part of the purpose at this stage is to begin to familiarize yourself with the account and the likely stakeholders. This information will be useful later on in several instances. 

Once messaging has been written for each persona and the lists have been built, the first wave of outreach should start. Choose 5-8 contacts from each list to reach out to in parallel. The spreadsheet pictured above can help to organize which contacts are being contacted while the rest live in the Sales Navigator lists. It’s likely that the prospector has access to a sales engagement platform (SEP) and can automate some of the steps in their sequences and remove most of the manual labor associated with reaching out to 50+ contacts in a day via phone and email. This is not the only way. A simple notepad application with a copy/paste version of each email and a few call scripts would certainly require a few extra clicks, but it is doable. This still leaves a gap in logging CRM activity but does give added flexibility. Either way, outreach can begin by making first calls and sending off initial emails to each of the first 5 prospects. 

As this outreach is cascading across the decision makers in each account and the prospector is trying to get bottom up information, keep an eye on each contact’s engagement level. Somewhere along the way, you're going to hit a patch where you don't have the phone numbers, no direct dial company number (some places don't even do this anymore), the job titles are obfuscated, and there's no social media profiles to be found. Any “Unsubscribe” or similar reply warrants swapping that contact with another from the list of 30. If the prospect is engaging with your emails via multiple opens or any clicks, the flank targets and visuals we started thinking about earlier come into play. There’s a LinkedIn feature that shows “People Also Viewed” profiles on the right side of a profile page in a vertical column. These people are likely connected to the target prospect in some way and can be reached for a referral into the prospect’s calendar. Since the prospect has been engaging with the content already, a response will likely result. If it’s “no thanks” simply go to the next prospect in your list. Any prospects who do not engage with your outreach in any way after 10-14 days should be swapped out for fresh contacts. Repeat this process until there’s a definitive report on each account you’d be proud to report back to the CRO. 

After Setting a Meeting

“Opportunities multiply as they are seized.”Sun Tzu

Once a meeting is set, use this meeting to multithread the account up front. Write a note (in the previous threads you’ve started) to the other stakeholders you’ve been reaching out to and humbly inform them of your victory. Something along these lines: 

Hey Jake, managed to set up a meeting with Bob Smith re: {thing you pitched Bob} – was hoping to loop you in if it makes sense? Would you like to hop in with us Monday at 2 or another time possibly? Thx -PWJ

After setting the meeting but before it occurs, whoever is going to attend the meeting should be fully prepared with notes on the account (number of employees, revenue, any relevant bits), discovery questions, need to know information, and a list of the other potential stakeholders the prospect will likely be able to confirm or deny. This is doing your homework. You’d be surprised what these tactics can do. Even if they don’t bite initially, take the first meeting and learn as much as you can. Make another pass with the information you gained in the first meeting. Rinse, repeat. Sequential meetings stack the knowledge gained about what’s going on inside the account and there’s a compound effect on your ability to communicate effectively with the people working there. Multithreading early will also shorten deal cycles. 

Conclusion

Becoming a signal in the noise is not an easy task at the enterprise level. These concepts are battle tested in the Fortune 100 account list and should be considered as one rep’s approach you can pull from or use entirely as a system, but the most important part is to think about how we’re getting on the calendar at such a company from first principles rather than rote replication of the steps. As more people consider these plays, it becomes less likely the techniques will work.

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