Cold Outreach for Enterprise Accounts: A Step By Step Playbook

May 3, 2023
 min read

In B2B sales, the old proverb “it's not what you know but who you know” can be a huge leg up when trying to land a massive enterprise deal. 

But what about those times when the opposite happens? Every salesperson faces the day that they’re given a high-priority account where they have exactly zero connections. It’s a daunting moment but it doesn't have to be and I’m going to show you how.

In this article, I'll guide you through my playbook I use to break into cold accounts and dig into each step along the way. We’ll cover how to:

  • Research customers (and the competition)
  • Craft persona based messaging
  • Implement your outreach strategy
  • Run successful sales meetings
  • Closing thoughts

Now, let’s break into that account.

Researching customers (and the competition)

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

Before diving into the top of the sales funnel, it's crucial to understand what's happening at the bottom and beyond.

By analyzing your recent successes and competition, you'll be better equipped to create a compelling value proposition that resonates with potential customers.

Analyze your existing customer base

To gain insights into your sales process, start by asking yourself these questions:

  • Why did the last 5 deals close?
  • What pushed those deals over the line? Why us and why now?
  • 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)?

Surprisingly, these questions often go unanswered while companies try to build an outbound sales motion.

Remember, it's not just the features of your product that will entice decision-makers; you need a deep understanding of the workflow you intend to impact. Buyers want to be seen, heard and understood, and answers to these questions are a great guiding light.

Study the competition

To better position your product in the market, it’s critical to know the competition.

Are you competing against a home-grown internal customized solution or another vendor? Chances are, you'll face both.

Create diagrams that showcase where your product sits in the competitive landscape. One useful approach is to create a 3-circle Venn diagram, a strategy popularized by Justin Michael (author of Tech-Powered Sales). Here’s an example:

These diagrams serve two purposes: they solidify your understanding of the competition, and they provide a compelling visual when prospecting and sparking interest. While you don’t have to create a diagram, having a way to visualize the competitive landscape can be incredibly helpful.

It’s also great to make battlecards to primary competitors, that capture things like:

  • Strengths and weakness of the competitor
  • How they position us and our counter POV
  • Why you win
  • Feature comparison
  • Pricing / packaging 
  • Questions to widen the gap for the buyer

Establish a strong value proposition

When targeting enterprise-level accounts, remember that these organizations are likely at a maturity level where most, if not all, potential bottlenecks in runtime-essential business operations have been identified and resolved. 

Demonstrating an understanding of their current problems and ways your product can be the solution will significantly improve the efficiency of your outreach efforts. 

Combine the knowledge you've gained from analyzing your existing customer base and studying your competition with your unique selling points and your prospects' needs and pain points. This will enable you to highlight your value in a way that resonates with prospects.

Researching your customers and the competition is a crucial first step that sets the foundation for the rest of your sales strategy. The more you know and the less you need to say, the better your outcome will be.

Craft persona based messaging

The bigger the deal, the more stakeholders involved in the business outcomes that your product or service aims to impact. Understanding key personas and their day-to-day is essential for successful account penetration. 

Develop buyer personas

To effectively connect with your prospects, you must be able to navigate the different tasks they’re responsible for and match people with their roles.

Utilize company job boards: Job postings often use internal language, providing key information about job functions for each title. This is valuable for selling complex products that impact multiple business units or for employing a flanking strategy. Research company websites, LinkedIn profiles, and other online resources to gather insights into each role's responsibilities, goals, and pain points.

Gather knowledge from various sources: Don’t just rely on Google to tell you everything you need to know. Branch out and talk to other sales reps, marketing, customers, read reviews of your product as well as competitors. The more depth in your sources, the more well rounded your personas will be.

Craft tailored messaging

A well-thought-out messaging strategy should leverage three layers of personalization:

Common connections: Utilize tools like LinkedIn Sales Navigator to find first and second-degree connections between your CEO and prospects. Leverage mutual connections for introductions or testimonials that can boost credibility and trust.

Prospect's work history compared to your client list: Reference the prospect's previous companies and relate how you've helped them. (For example: “Noticed your time at Acme, we help them do X - was hoping to go over some similar ideas for Gammacorp.”) Target prospects who have recently changed roles or received promotions, as they may have new budgets and a desire to make an impact. Share case studies or success stories that demonstrate your solution's value for similar organizations or industries.

Prospect-authored content: Comment on their posts, share insights from their articles, or discuss points from their presentations to personalize your messaging.

Forced personalization is probably the worst thing you can do – prospects can smell it a mile away. Instead, focus on potential business problems you can solve and the outcomes others have achieved with your solution. 

Craft messaging that resonates with each persona by addressing their unique concerns, goals, and interests. To make it simple, we think of messaging as needing the 3 P’s: persona, pain point and value proposition.

The Chrome extension makes sales email personalization a snap - it’s able to pull data on your prospect using their LinkedIn and Twitter personal and company feeds, funding announcements, articles, and more, and generate a contextually relevant email to them using those inputs.

Tailor messaging to different seniority levels

As you craft your messaging, consider the different priorities of C-level, VP, and Director or Manager-level executives:

C-level executives: Focus on a vision for the future and decisions impacting the next 3-5 years. Emphasize strategic alignment, long-term growth, and competitive advantages. Showcase how your solution can support company-wide initiatives or industry trends.

VP level executives: Aim for decisions impacting the next 3-6 months. Highlight tactical improvements, resource optimization, and team performance. Provide examples of how your product can streamline processes, reduce costs, or enhance collaboration.

Director and Manager-level subordinates: Address immediate impact for promotion or leveraging results for better titles elsewhere. Demonstrate quick wins, actionable insights, and practical tools. Offer hands-on assistance, training, or resources to help them succeed with your solution.

Think in terms of both job function and seniority. A great way to do this is to create a messaging matrix targeting various job functions (e.g., Sales, Marketing, and RevOps) and seniority levels (C-level, VP, and Director).

Implement persona-based differentiation

Persona-based differentiation is an efficient messaging approach because it requires most of the work to be done upfront. By tailoring your messaging to each persona's workflow and level of seniority, you can ensure that your messaging will have an impact.

Develop a messaging matrix: Create a grid that outlines the messaging for each combination of job function and seniority level. Identify the unique pain points, goals, and concerns for each persona and seniority level. Adjust your messaging to align with the needs and priorities of each target group.

Test and refine messaging: Monitor the performance of your messaging by tracking engagement metrics, such as email open rates, reply rates, and meeting conversion rates. Analyze feedback from prospects to identify areas for improvement or gaps in your messaging. Continuously tweak and refine your messaging based on real-world results and feedback.

Leverage automation tools: Use marketing automation and sales engagement platforms to help manage and execute your persona-based messaging strategy. Schedule and send personalized emails, follow-up messages, and reminders at the right time and frequency for each persona. Automate lead scoring, segmentation, and nurturing processes to ensure that prospects receive the most relevant and timely messaging.

Regie Rapid Writer allows enterprise sales teams to personalize their cold outbound emails with one click, using pre-defined personas and value proposition language from the CMS.

Implement your outreach strategy

To break into enterprise accounts, you'll need to build a targeted list of potential decision-makers within each organization. Here’s how to create your list and design a multi-channel outreach strategy.

Build a targeted prospect list

Utilize LinkedIn Sales Navigator: For each account you're targeting, create a corresponding list in LinkedIn Sales Navigator. Use Boolean operators (AND, OR, NOT) in keyword searches, combined with the internal language from your job description research, to filter through thousands of employees in each account.

Save at least 30 contacts per list: Focus on at least 30 contacts for each account to familiarize yourself with the organization and its stakeholders.

Reach out to prospects

Choose 5-8 contacts from each list: Once you have tailored messaging for each persona and built your lists, initiate your first wave of outreach. Select 5-8 contacts from each list to contact simultaneously. Use a spreadsheet to organize your outreach efforts, while keeping the rest of the contacts in Sales Navigator. We like to use a three deep, three wide strategy, where you go three layers into a functional area (say VP of Sales, Director of Sales and Sales Manager), and then three layers across (say Sales, Marketing, and Operations), to pick the top five people to prospect.

Leverage sales engagement platforms (SEPs) or simple tools: You probably have access to an SEP, like Outreach or Salesloft, that can automate some of the steps in your outreach sequences, making it easier to manage communication with 50+ contacts per day. However, if you don't have access to an SEP, using a simple notepad application with copy/paste versions of your emails and call scripts can still be effective – though that involves more manual labor.

Building sequences can be time and labor-intensive. can reduce that weeks long process down to a few minutes, using a database of performant content and Generative AI to build persona based sequences you can publish directly into your SEP.

Nurture and follow-up

Monitor engagement levels: As you reach out to decision-makers in each account, keep an eye on each contact's engagement level. Any time you see “unsubscribe” or a similar reply, swap that contact with another from your list of 30.

Utilize LinkedIn's "People Also Viewed" feature: When a prospect engages with your emails through multiple opens or clicks, consider leveraging LinkedIn's "People Also Viewed" feature on a prospect's profile page. This can help you identify people connected to the prospect, who you can then reach out to for a referral. Since the prospect has already been engaging with your content, you'll likely receive a response. If it's a "no thanks," simply move on to the next prospect on your list.

Replace unresponsive contacts: Any prospects who do not engage with your outreach in any way after 10-14 days should be swapped out for fresh contacts. Keep iterating this process until you have a definitive report on each account that you'd be proud to present to your Chief Revenue Officer (CRO).

By following this approach to list building and targeting, you'll have a systematic process for breaking into enterprise accounts that will put your sales efforts on a strong foundation.

Run successful sales meetings

“Opportunities multiply as they are seized.”Sun Tzu

Got a meeting? Awesome. Now it's time to capitalize and lay the groundwork for a successful sales process. To make the most of this chance, here’s what to do next:

Prepare for the meeting

Multithread the account up front: After setting the meeting, loop in other stakeholders that you've been reaching out to. Send a friendly note to inform them of your progress and invite them to join the discussion. For example:

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 - Rocco

Do your homework: Research the prospect and their organization thoroughly. This includes details such as the number of employees, revenue, and any other relevant information that will help you understand their needs better.

Develop a list of discovery questions: Prepare a set of questions that will help you uncover the prospect's pain points, goals, and expectations. These questions will guide your conversation and enable you to tailor your pitch accordingly.

Generative AI platforms like can surface communication preferences, such as communication advice and personality DISC and OCEAN profiles to make recommendations on communication best practices to assist with call prep.

Run a successful meeting

Build rapport: Start the meeting by establishing a connection with the prospect. Show genuine interest in their needs and demonstrate your expertise by asking thoughtful questions and sharing valuable insights.

Address objections and concerns: Be prepared to handle any objections or concerns the prospect may have. Listen carefully to their feedback, and address it confidently and professionally.

Closing thoughts

Cracking into enterprise accounts and standing out amidst the clutter is no walk in the park. Persistence is key. But by following these actionable steps, you'll be well on your way to securing new business and driving revenue growth.

The strategies we've discussed have proven their mettle in the world of Fortune 500 accounts, and can serve as a valuable blueprint for your own enterprise sales journey. But it’s crucial not to simply follow them blindly – you’ll need to adapt and modify them to suit your individual circumstances.

As the SaaS landscape becomes increasingly competitive, it’s more important than ever to get an edge. That’s where using Sales AI to enhance your outreach can help you stay ahead of the curve.

By implementing these field-tested methods and making them your own, you’ll turn your team into a true enterprise sales powerhouse. 

Last bit of advice: don’t wait! Just get out there and start putting these strategies into action.

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