Prospecting enterprise accounts: A step-by-step guide & FAQs

In the world of sales, landing an enterprise account is like hitting the jackpot. It's exciting, potentially game-changing, and — let's face it — a little intimidating. But here's the thing: with the right approach, even the biggest whales can be reeled in.

This guide is your roadmap to navigating the sometimes choppy waters of enterprise prospecting. We'll walk you through everything from identifying what makes an account "enterprise" to closing the deal. 

Let's get started!

Building an enterprise prospecting plan: The “5 p’s of prospecting” approach

When it comes to enterprise prospecting, success isn't just about having a plan: it's about having the right approach that covers all crucial aspects of the process. This is where the "5 p's of prospecting" framework comes into play. Every successful prospecting motion, particularly at the enterprise level, needs to meet specific criteria to be effective. The "5 p's" encapsulate these essential elements:

1. Preparation
2. Personas
3. Positioning
4. Personalization
5. Persistence

In this section, we'll walk you through each of these criteria, explaining why they're critical for enterprise prospecting success. By understanding and incorporating these elements into your approach, you'll be well-equipped to tackle the complexities of enterprise sales. Then, in the following section, we'll show you how to apply this framework to create a step-by-step prospecting plan that puts these principles into action.

Now, keep in mind that there’s no one “right” “5 p’s” framework to rule them all. In fact, if you Google “5 p’s of prospecting,” you’ll find scores of other companies and sellers who have their own spin on the concept in terms of what “p”-words make up their framework. Frankly, it doesn’t matter what everyone else is doing; what matters more is what works for you, your business, and – more importantly – your buyers. We’ve found a lot of success with the “5 p’s” framework laid out above, so that’s what we’ll speak to in this section.

The “5 p’s of prospecting” framework: An overview

The “5 p’s of prospecting” framework is designed to provide you with criteria to help you cover all your bases when it comes to building effective enterprise prospecting plans. Here’s a little overview of what each “p” stands for and involves.

1. “Preparation”

This stage is the “do your homework” stage. Preparation is all about gathering intelligence and setting the stage for your prospecting efforts. This foundational step ensures you're targeting the right companies and understanding the landscape before you make any moves.

• Goal: Do your homework and lay the groundwork for your prospecting efforts.
• Types of activities: Here are examples of the kinds of tasks and activities that would complete the “Preparation” criterion”:
  • Define your ideal customer profile.
  • Build your target account list.
  • Research each account.
  • Analyze the competitive landscape.
  • Set realistic timelines.
  • Establish clear goals.
  • Manage internal expectations.

2. “Personas”

With your groundwork laid, it's time to zoom in on the individuals within your target organizations. Personas take your preparation to the next level by creating detailed profiles of the decision-makers and influencers you'll be engaging with.

• Goal: Gain a deep understanding of who your audience is, what their needs are, and what causes them pain or frustration in their day-to-day work life.
• Types of activities: Here are examples of the kinds of tasks and activities that would complete the “Personas” criterion”:
  • Develop robust personas.
  • Familiarize yourself with each persona’s pain points.
  • Understand each persona's role & influence in the decision-making process.
  • Map each persona’s buyer journey.

3. “Positioning”

Part of a successful outreach strategy is ensuring that your solution stands out among the competition. This step is about articulating your unique value proposition in a way that resonates with your target personas and addresses their specific pain points.

• Goal: Figuring out what characteristics make your brand stand out in the crowd. What truly differentiates you from the competition?
• Types of activities: Here are examples of the kinds of tasks and activities that would complete the “Positioning” criterion”:
  • Establish your unique value proposition(s).
  • Craft your competitive positioning strategy.
  • Go beyond features: position your brand as a problem solver.

4. “Personalization”

Armed with knowledge about your personas and their pain points, you can now create highly targeted, personalized outreach strategies. This step is where you translate your insights into action.

• Goal: Crafting tailored approaches for each prospect – at scale.
• Types of activities: Here are examples of the kinds of tasks and activities that would complete the “Personalization” criterion”:
  • Craft messaging tailored to each persona’s situation & industry.
  • Plan individualized outreach strategies for each persona.

5. “Persistence”

Finally, with all the other elements in place, it’s time to make your plan – and one that can last for the long haul. Enterprise sales don't happen overnight, so this step focuses on creating a sustained, value-driven engagement strategy.

• Goal: Maintaining momentum to stay top of mind during long sales cycles.
• Types of activities: Here are examples of the kinds of tasks and activities that would complete the “Persistence” criterion”:
  • Use a multi-threaded approach to outreach.
  • Develop an omnichannel outreach strategy.
  • Implement a nurture strategy to ensure long-term engagement.

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How to prospect an enterprise account: A step-by-step guide 

Now that you’ve learned what the “5 p’s of prospecting” are, we’ll teach you how to apply this framework when creating an enterprise prospecting plan. Specifically, we'll walk you through all the steps you need to take – from defining your ideal customer to creating long-term engagement plans – and give you some guidance or suggestions for how to complete each step effectively. 

Here's a high-level overview of the steps involved in prospecting an enterprise account. This is a longer section, so feel free to use the links below to jump to the specific step(s) you'd like to learn more about:

• Step #1: Define your ideal profile.
• Step #2: Build your target account list.
• Step #3: Do your homework on each account.
• Step #4: Do your homework on your competitors.
• Step #5: Set realistic timelines.
• Step #6: Establish clear goals.
• Step #7: Manage internal expectations.
• Step #8: Develop robust personas.
• Step #9: Familiarize yourself with each persona’s pain points.
• Step #10: Understand each persona's role and influence in the decision-making process.
• Step #11: Map each persona’s buyer journey.
• Step #12: Establish your unique value proposition(s).
• Step #13: Craft your competitive positioning strategy.
• Step #14: Going beyond features: position your brand as a problem solver.
• Step #15: Craft messaging tailored to each persona’s situation & industry.
• Step #16: Plan individualized outreach strategies for each persona.
• Step #17: Use a multi-threaded approach to outreach.
• Step #18: Develop an omnichannel outreach strategy.
• Step #19: Implement a nurture strategy to ensure long-term engagement.
  

Let's get started!

Step #1: Define your ideal customer profile.

“5 P’s” stage: Preparation

Having an ideal customer profile (ICP) locked down is like having a treasure map for your prospecting journey. It helps you focus your efforts on the right companies (and the right contacts), saving your team valuable time and resources. By clearly defining your ICP, you'll be able to spot the most promising opportunities and tailor your approach to their specific needs.

Here are some ways to tackle this step effectively:

• Analyze your most successful enterprise clients. Ask yourself questions like:
  • “Why did the last 5 deals close?” Identify the key factors that sealed the deal. Was it a unique feature, pricing, or something else?
  • “What pushed those deals over the line?” Why did these customers choose you, and why did they decide to buy now?
  • “How do customers describe the workflow you’re impacting?” Listen to how they talk about the problems your product solves.
  • “What downstream business outcomes are you unlocking?” Understand how your solution creates value beyond the immediate problem it addresses.
  • “What are the current workflow problems?” Know the specific issues or inefficiencies in the existing workflow that your product solves.
  • “How is the customer solving this right now?” Are they using internal solutions, other vendors, or maybe a mix of both?
• Use information about your current customers to create a detailed ICP.
  • Consider factors such as:
    • Industry or vertical (e.g., healthcare, finance, manufacturing)
    • Company size (e.g., employee count and annual revenue)
    • Geographic location and market reach (e.g., local, national, global)
    • Organizational structure (e.g., centralized vs. decentralized decision-making)
    • Technology stack and level of digital maturity
    • Business model (e.g., B2B, B2C, hybrid)
  • Identify common pain points and challenges these companies face that your solution addresses.
  • Consider the typical buying process and decision-making structure in these organizations.
  • Look at the job titles and roles of your key contacts within these companies.
  • Use customer interviews or surveys to gain deeper insights into what makes these clients a good fit.
  • Develop a scoring system to rate potential prospects based on how similar they are to your ICP.
• Validate your ICP against the market to ensure sufficient opportunities.
  • Use market research tools and industry reports to estimate your ICP's total addressable market (TAM).
  • Get feedback on your ICP from your sales and marketing teams to ensure that it aligns with their experiences and observations.
  • Consider creating multiple ICPs if you discover distinct segments within your target market.
  • Analyze your sales pipeline to see how many current opportunities align with your defined ICP.
  • Speak with industry experts or consultants to validate your assumptions about the market.
  • Regularly review and refine your ICP based on new data and changing market conditions.
  • Create a feedback loop with your customer success team to continually validate and update your ICP based on actual customer experiences.

Step #2: Build your target account list.

“5 P’s” stage: Preparation

Creating a focused list of target accounts is crucial for effective enterprise prospecting. This step helps you narrow down your efforts to a manageable number of high-potential companies. By identifying these key accounts, you can dedicate more time and resources to thoroughly researching and engaging with each one, increasing your chances of success.

Here are some ways to tackle this step effectively:

• Use sales intelligence tools to identify companies matching your ICP.
  • Use LinkedIn Sales Navigator or similar tools to search for companies matching your ICP criteria.
  • Use Boolean operators (AND, OR, NOT) in your keyword searches to refine results, incorporating internal language from your job description research. 
  • This helps you filter through thousands of employees and pinpoint the key players.
• Prioritize accounts based on fit, potential deal size, and strategic importance.
  • Develop a scoring system to rate accounts based on how closely they match your ICP.
  • Consider factors like:
    • Firmographic fit (how well they match your ICP)
    • Potential deal size (based on company size, budget, or other relevant factors)
    • Strategic importance (e.g., potential for expansion, industry influence, or alignment with company goals)
    • Current pain points or challenges that your solution can address
    • Recent trigger events (e.g., new leadership, funding rounds, expansions) that could create opportunities
  • Use a weighted scoring system if some factors are more important than others.
  • Consider using account-based marketing (ABM) platforms to help with account selection and prioritization.
  • Get feedback from your marketing and customer success teams on your target account criteria and make sure you're all aligned.
• Aim for a focused list of 20-30 high-quality targets to start.
  • Quality over quantity: It's better to have a smaller list of well-researched, high-potential accounts than a large list of poorly-fit prospects.
  • Consider your team's capacity: Ensure you have the resources to effectively engage with each account on your list.
  • Group your target accounts into tiers (e.g., Tier 1, 2, 3) based on their priority and potential value.
  • Create account dossiers or one-pagers summarizing key information for each target account.
  • Plan to review and refresh your target account list regularly (e.g., quarterly) based on new information and changing market conditions.
  • Consider creating a "watch list" of additional accounts that didn't make your top 20-30 but could be potential targets in the future.

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Step #3: Do your homework on each account.

“5 P’s” stage: Preparation

Thorough research is the foundation of successful enterprise prospecting. By diving deep into all the key details of each account, you'll be better equipped to understand their needs and pain points. Having this information will allow you to craft more relevant and compelling pitches, showing prospects that you've done your homework and truly understand their situation.

Here are some ways to tackle this step effectively:

• Understand their business model, recent news, and industry challenges.
  • Study the company's website, focusing on their "About Us," "Products/Services," and "Investors" pages to grasp their business model.
  • Review their annual reports and quarterly earnings calls for insights into financial health and strategic priorities.
  • Set up Google Alerts for the company name and key executives to stay on top of recent news and developments.
  • Analyze industry reports from sources like Gartner or Forrester to identify sector-specific trends and challenges.
  • Look for recent press releases or news articles about the company's expansion plans, new product launches, or strategic partnerships.
  • Check their social media accounts (LinkedIn, Twitter, Facebook) for recent announcements or initiatives.
• Identify key stakeholders and decision-makers at each account.
  • Use tools like LinkedIn Sales Navigator to map out the organizational structure and find relevant decision-makers.
  • Look for executives and managers in relevant departments that would benefit from your solution (e.g., IT, Finance, Operations).
  • Pay attention to recent hires or promotions, as these often signal new initiatives or strategic shifts.
  • Check if the company has published any case studies or success stories about implementing similar solutions, which might reveal key players in their buying process.
  • Consider industry-specific roles that might be unique to your prospect's sector (e.g., for finance, it might be the chief risk officer; for healthcare, it would be the chief medical officer).
  • Use tools like Hunter.io or Clearbit to find email addresses and contact information for key stakeholders.
• Map out the potential buying committee (e.g., economic buyer, technical buyer, user buyer, etc.).
  • Understand the typical roles involved in enterprise purchasing decisions:
    • Economic buyer: Usually a C-level executive who controls the budget and gives final approval.
    • Technical buyer: Often an IT manager or director who evaluates the technical aspects and integration requirements.
    • User buyer: Typically a department head or manager who will oversee the day-to-day use of your solution.
    • Influencers: Could include consultants, advisors, or other department heads affected by the purchase.
  • Research the company's org chart to identify who might fill these roles.
  • Look for any publicly available information on the company's procurement process or decision-making structure.
  • Use LinkedIn to see if you have any mutual connections who might provide insights into the company's decision-making process.

Step #4: Do your homework on your competitors.

“5 P’s” stage: Preparation

Understanding your competition is crucial in enterprise sales. It not only helps you position your offering more effectively but also prepares you for potential objections and comparisons prospects might make. By thoroughly researching your competitors, you'll be better equipped to highlight your unique value proposition and address any concerns head-on.

Here are some ways to tackle this step effectively:

• Analyze your competitive landscape:
  • Conduct a SWOT analysis on each competitor, identifying:
    • Strengths; 
    • Weaknesses; 
    • Opportunities;
    • Threats
  • Create comparison charts highlighting your advantages
  • Identify gaps in competitors' offerings that you can fill
• Monitor competitors' online presence:
  • Regularly check their websites for product updates and new features
  • Follow competitors' social media accounts to get real-time updates on company news, as well as to observe  customer interactions
  • Set up Google Alerts for your competitors' names and key products
• Leverage sales intelligence tools:
  • Use platforms like G2, Capterra, or TrustRadius to gather customer reviews and ratings
  • Employ competitive intelligence tools like Crayon or Kompyte for automated insights
• Engage in mystery shopping:
  • Sign up for competitors' free trials or demos to experience their sales process
  • Attend their webinars or virtual events to understand their messaging and tactics
• Analyze financial reports and press releases:
  • For public companies, review their quarterly earnings calls and annual reports
  • Stay updated on press releases for insights into product launches and strategic moves
• Gather intel from industry events:
  • Attend trade shows and conferences where competitors are present
  • Network with industry professionals to gain insights on competitor perceptions
• Study their customer base:
  • Identify key accounts they're working with and analyze case studies
  • Look for patterns in the types of clients they attract or industries they focus on
• Examine their talent acquisition:
  • Monitor their job postings to understand areas of expansion or focus
  • Track key hires or departures for insights into strategic shifts
• Analyze their content strategy:
  • Review their blog posts, whitepapers, and other content to understand their messaging
  • Identify topics they're focusing on to gauge market trends and priorities

Step #5: Set realistic timelines.

“5 P’s” stage: Preparation

Setting realistic timelines is crucial in enterprise sales, where cycles can be long and complex. This step helps manage expectations, both for yourself and your team. By planning for extended nurturing periods and creating milestones, you can track progress even when deals aren't closing immediately, keeping motivation high and ensuring steady momentum.

Here are some ways to tackle this step effectively:

• Develop quarterly and annual forecasts that account for longer sales cycles.
  • Analyze historical data from past enterprise deals to understand typical sales cycle lengths in your industry.
  • Break down the sales process into stages (e.g., initial contact, needs assessment, proposal, negotiation, closing) and estimate timeframes for each.
  • Factor in potential delays such as budget approval cycles, stakeholder reviews, and legal processes.
  • Use a sales forecasting tool or CRM to create data-driven projections that account for these longer timelines.
  • Build in buffer time for unexpected setbacks or extended decision-making processes.
  • Review and adjust your forecasts based on data and changing market conditions.
• Plan for extended periods of nurturing before seeing concrete results.
  • Develop a long-term nurture strategy that provides value to prospects over an extended period.
  • Create a content calendar with regular touchpoints (e.g., monthly industry insights, quarterly webinars) to stay top-of-mind.
  • Set up automated email sequences that drip-feed relevant information over time.
  • Plan for periodic check-ins or "health checks" with prospects to reassess their needs and timing.
  • Allocate resources for long-term relationship building activities like executive roundtables or industry events.
  • Establish KPIs for nurturing activities (e.g., engagement rates, meeting requests) to track progress during the extended sales cycle.
• Create milestones to track progress even when deals aren't closing.
  • Break down the sales process into smaller, achievable milestones that indicate forward movement.
  • Examples of milestones could include:
    • Successfully scheduling an initial meeting with a key decision-maker
    • Getting invited to participate in an RFP process
    • Securing a product demo or pilot program
    • Getting introduced to additional stakeholders in the buying committee
  • Use your CRM to set up stage progression tracking and milestone alerts.
  • Develop a point system for different activities and milestones to quantify progress.
  • Create visual dashboards that showcase milestone achievements for team motivation.
  • Regularly celebrate small wins and progress markers with your team.
  • Use milestone data to identify potential bottlenecks in your sales process and optimize your approach.

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Step #6: Establish clear goals.

“5 P’s” stage: Preparation

As with any other business activity, having clear goals can help guide you through your prospecting efforts. Think of them almost as your North Star: they provide direction and help you measure progress in a landscape where immediate results are rare. Additionally, using a goal-setting framework like SMART allows you to break down your overall objectives into smaller, more achievable targets. This allows you to create a roadmap for success that can keep you focused and motivated, even when the sales cycle drags on.

Here are some ways to tackle this step effectively:

• Define SMART objectives for your enterprise prospecting efforts.
  • Specific: Clearly define the outcome that you want to achieve. For example, "Secure 5 meetings with C-level executives at Fortune 500 companies in the healthcare sector."
  • Measurable: Ensure you can quantify your progress. For instance, "Increase engagement rate with prospecting emails by 20%."
  • Achievable: Make sure that the outcome you want to achieve is realistic, based on your available resources and market conditions. Example: "Convert 2% of qualified leads into paying customers within the next 12 months."
  • Relevant: Align the outcome you want to achieve with your overall business strategy. For example: "Expand our enterprise client base in the finance sector by 15% this year."
  • Time-bound: Set deadlines to create urgency. For instance: "Book 10 product demos with new enterprise prospects by the end of Q2."
  • Use a goal-setting template or software to document and track your SMART objectives.
  • Review and adjust your SMART goals regularly based on market changes and your progress.
• Break down annual goals into quarterly and monthly targets.
  • Start with your annual goal and work backwards to create smaller, incremental targets.
    • For example, if your annual goal is to close 10 enterprise deals:
      • Quarterly target: Close 2-3 deals per quarter
      • Monthly target: Close 1 deal per month or progress 2-3 deals to the next sales stage
  • Create a visual roadmap or timeline to illustrate these broken-down goals.
  • Set activity-based targets that contribute to your overall goals, such as:
    • Number of outreach attempts per week
    • Number of discovery calls scheduled per month
    • Number of proposals sent per quarter
  • Use project management tools or CRM systems to track progress on these smaller targets.
  • Schedule regular check-ins (weekly / bi-weekly) to go over progress on monthly and quarterly goals.
• Align your goals with overall company objectives.
  • Meet with leadership to understand the company's strategic priorities for the year.
  • Identify how your enterprise prospecting efforts can directly contribute to these larger objectives.
    • For example, if the company aims to expand into new markets, set goals around prospecting in those specific regions or industries.
  • Consider how your goals impact other departments:
    • Work with marketing to align on lead generation targets
    • Collaborate with product teams to understand upcoming features that could attract enterprise clients
    • Coordinate with customer success to ensure readiness for onboarding new enterprise accounts
  • Develop a "goal hierarchy" that shows how your prospecting goals ladder up to department and company-wide objectives.
  • Present your aligned goals to leadership for feedback and buy-in.
  • Be prepared to adjust your goals if company priorities shift during the year.

Step #7: Manage internal expectations.

“5 P’s” stage: Preparation

Managing internal expectations is key to maintaining support for your enterprise prospecting efforts. By educating your team and leadership on the unique challenges of enterprise sales, you can prevent frustration and misalignment. Regular updates and carefully chosen KPIs help demonstrate progress, even when deals aren't closing quickly, ensuring continued buy-in for your long-term strategy.

Here are some ways to tackle this step effectively:

• Prepare materials to educate your team and leadership on enterprise sales cycles.
  • Develop a presentation that provides a visual timeline of typical enterprise sales cycles and breaks down the stages of an enterprise sale, explaining the activities and time involved in each.
  • Compile case studies from your industry showing typical timelines for successful enterprise deals.
  • Prepare a FAQ document addressing common questions about enterprise sales (e.g., "Why does it take so long?", "What's happening when we don't see immediate results?").
  • If necessary, organize lunch-and-learn sessions or workshops to present this information and foster discussion.
• Plan regular updates to keep stakeholders informed of progress, even when it's slow.
  • Set up a consistent schedule for updates (e.g., bi-weekly emails, monthly meetings) to create a rhythm of communication.
  • Create a standardized report template that highlights both quantitative progress (e.g., number of touch points, meetings scheduled) and qualitative insights (e.g., feedback from prospects, industry trends).
  • Use a traffic light system (red, yellow, green) to quickly communicate the status of different prospecting efforts or accounts.
  • Implement a digital dashboard that stakeholders can access anytime to see real-time progress.
  • Prepare brief "success spotlights" that showcase small wins or positive interactions, even if they haven't resulted in closed deals yet.
  • Host quarterly review sessions to provide a more comprehensive overview of progress and adjust strategies as needed.
• Develop KPIs that show progress in the early stages of enterprise prospecting.
  • Track the number of new contacts added within target accounts to show progress in multi-threading.
  • Report on the percentage of target accounts that have progressed to each stage of your sales pipeline.
  • Monitor the number of referrals or introductions received within target accounts.
  • Measure the quality of your prospecting efforts by tracking the seniority level of engaged contacts.
  • Implement a "relationship depth" metric that combines factors like frequency of interaction, number of stakeholders engaged, and level of information shared.
  • Measure the "account penetration rate" - the percentage of key stakeholders you've engaged within each target account.
  • Create a "pipeline value" KPI that assigns potential values to deals at each stage, even before they're officially opportunities.

Step #8: Develop robust personas.

“5 P’s” stage: Personas

When it comes to prospecting overall, personas are your secret weapon. They go beyond basic demographics to give you a deep understanding of your key stakeholders. By creating detailed profiles of decision-makers and influencers, you can easily adjust your approach to resonate with each person's specific needs, challenges, and goals, increasing your chances of making meaningful connections.

Here are some ways to tackle this step effectively:

• Create detailed personas that go beyond basic demographic information.
  • Start with job title and role, but dig deeper into details like:
    • Career path and background
    • Key responsibilities
    • Daily challenges and priorities
    • Information sources they trust (e.g., industry publications, thought leaders)
    • Professional goals and aspirations
    • Communication preferences (e.g., email, phone, social media)
    • Decision-making style (e.g., analytical, intuitive, collaborative)
  • Consider personal factors that might influence their professional life:
    • Age range and generational characteristics
    • Education level and field of study
    • Personal interests or hobbies that might provide connection points
    • Values and motivations (e.g., innovation, stability, growth)
  • Use tools like empathy maps to visualize what your personas think, feel, say, and do
• Use a "3-deep, 3-wide" strategy to build your personas.
  • First, identify your key decision-maker(s):
    • Usually a C-level executive or senior manager with budget authority
    • Research their specific role and responsibilities within the organization
    • Understand their strategic priorities and how they align with your solution
  • Then, create personas for the three positions under them:
    • These are often the implementers or day-to-day users of your solution
    • Focus on their operational challenges and how your product can make their jobs easier
    • Understand their influence on the decision-maker and what they need to build a business case
  • Then, create personas for the three positions beside them:
    • These could be peers or leaders of adjacent departments affected by the decision
    • Understand how your solution impacts their areas and what concerns they might have
    • Identify potential allies or obstacles among these lateral influencers
• For each persona, identify who they are, their pain points (more on this in the next bullet), and what they need to solve those pain points.
  • For each persona in this framework, consider:
    • Their role in the decision-making process (e.g., initiator, influencer, gatekeeper, decider, user)
    • The types of information they need to move the process forward
    • Potential objections or concerns specific to their position
  • Who they are:
    • Create a fictional name and brief bio to humanize the persona
    • Summarize their role, responsibilities, and place in the organization
    • Highlight their key goals and challenges
  • Their pain points:
    • List specific problems or frustrations they face in their role
    • Identify inefficiencies or bottlenecks in their current processes
    • Consider both personal pain points (e.g., time management, stress) and organizational pain points (e.g., budget constraints, compliance issues)
  • What they need to solve those pain points:
    • Outline how your solution addresses each identified pain point
    • Specify the features or benefits that are most relevant to this persona
    • Identify the outcomes or results that would be most meaningful to them
    • Consider what evidence or proof points would be most convincing for this persona
• Remember, three to four personas usually account for over 90% of your purchases.
  • Prioritize personas based on their influence in the buying process and relevance to your solution
  • Focus on developing deep, well-researched personas for the most critical roles
  • Review and update your personas based on real interactions and feedback
  • Use your CRM to tag contacts with their corresponding persona for easy reference and personalized outreach

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Step #9: Familiarize yourself with each persona’s pain points.

“5 P’s” stage: Personas

Understanding pain points is crucial for effective prospecting. By digging deep into the specific challenges each persona faces, you can position your solution as the answer to their problems. In B2B sales, addressing the value to the specific person you’re talking to – in addition to value to their business – can significantly boost your chances of success. This step helps you speak directly to what keeps your prospects up at night.

Here are some ways to tackle this step effectively:

• Dig deep into the specific challenges and problems that each persona faces.
  • Conduct thorough research using:
    • Industry reports and trends
    • Company financial reports and earnings calls
    • Social media posts and professional forums
    • Customer reviews and feedback for similar products
  • Use open-ended questions to uncover hidden pain points
  • Look for both explicit pain points (openly expressed challenges) and implicit pain points (underlying issues they may not directly mention)
  • Categorize pain points into different areas:
    • Financial (e.g., high costs, budget constraints)
    • Productivity (e.g., inefficient processes, time-consuming tasks)
    • Process (e.g., bottlenecks, compliance issues)
    • Support (e.g., lack of resources, inadequate training)
  • Create a pain point matrix for each persona, mapping challenges to potential solutions
• Focus on personal value, not just company value.
  • Understand that B2B decision-makers are 50% more likely to buy when they see personal value
  • Identify how your solution can:
    • Make their job easier or more efficient
    • Enhance their professional reputation or career prospects
    • Reduce their stress or workload
    • Help them achieve personal goals or KPIs
  • Consider the emotional aspects of their challenges, such as:
    • Fear of failure or making wrong decisions
    • Desire for recognition or advancement
    • Need for security or stability in their role
• Don't just sell a product; sell a solution to their pain points.
  • Map your product features directly to specific pain points for each persona
  • Develop ROI calculators or value proposition tools tailored to each persona's priorities
  • Use case studies and testimonials that highlight pain point resolution for similar personas
  • Create comparison charts showing how your solution addresses pain points better than alternatives

Step #10: Understand each persona's role and influence in the decision-making process.

“5 P’s” stage: Personas

Knowing each persona's role in the decision-making process helps you tailor your approach to each stakeholder's level of influence and authority. By aligning your messaging with their specific goals and KPIs, you can more effectively demonstrate the value of your solution from their unique perspective.

Here are some ways to tackle this step effectively:

• Analyze how each persona fits into the decision-making process.
  • Identify their role in the buying journey:
    • Initiator: Who first recognizes the need for a solution?
    • Influencer: Who shapes opinions and requirements?
    • Gatekeeper: Who controls information flow and access to decision-makers?
    • Decision-maker: Who has the final say?
    • User: Who will actually use the solution day-to-day?
    • Buyer: Who manages the procurement process?
  • Determine at which stages each persona is most active and influential
  • Understand the internal dynamics and relationships between different personas
  • Identify potential champions who can advocate for your solution internally
  • Recognize potential blockers and plan strategies to address their concerns
• Identify their level of influence and authority.
  • Assess their position in the organizational hierarchy
  • Understand their authority (if any) over budget and spending
  • Evaluate their ability to influence others in the organization
  • Consider their expertise and credibility within their field
  • Analyze their track record of driving change or implementing new solutions
  • Understand their decision-making autonomy vs. need for consensus or approval
  • Consider their influence on defining requirements and evaluation criteria
• Understand their specific goals and KPIs.
  • Research industry-standard KPIs for each persona's role
  • Analyze company reports and public statements to identify stated goals
  • Understand how your solution aligns with or impacts those KPIs:
    • Financial metrics (e.g., ROI, cost reduction, revenue growth)
    • Operational metrics (e.g., efficiency, productivity, time-to-market)
    • Customer-related metrics (e.g., satisfaction scores, retention rates)
    • Innovation metrics (e.g., new product development, digital transformation progress)
  • Recognize any pressures or mandates from higher management that influence their goals
  • Understand how economic, industry, or market trends are shaping their priorities
  • Consider how your solution can help them achieve quick wins as well as long-term objectives

Step #11: Map each persona’s buyer journey.

“5 P’s” stage: Personas

Mapping the buyer journey for each persona helps you anticipate their needs at every stage. This step allows you to plan how you'll provide value throughout their decision-making process. By understanding the key touchpoints and information needs at each stage, you can ensure you're always one step ahead, offering the right information at the right time.

Here are some ways to tackle this step effectively:

• Outline the typical buying journey for each persona.
  • Break down the journey into key stages:
    • Awareness: Recognizing a problem or opportunity
    • Consideration: Researching potential solutions
    • Evaluation: Comparing specific options
    • Decision: Selecting a solution and negotiating terms
    • Implementation: Adopting and integrating the solution
    • Expansion: Considering additional features or use cases
  • Identify how each persona moves through these stages:
    • What triggers their entry into each stage?
    • How long do they typically spend in each stage?
    • What are their primary concerns or questions at each point?
  • Map out potential detours or roadblocks in the journey.
  • Understand how different personas interact during the journey.
• Identify key touchpoints and information needs at each stage.
  • Awareness:
    • Thought leadership content (blogs, whitepapers, industry reports)
    • Social media posts highlighting industry trends or challenges
    • Targeted advertising addressing pain points
  • Consideration:
    • Product overviews and feature comparisons
    • Case studies and success stories
    • Educational webinars or video content
  • Evaluation:
    • Detailed product specifications
    • Customized demos or trials
    • ROI calculators or value estimation tools
    • Technical documentation or integration guides
  • Decision:
    • Proposal documents
    • References from similar customers
    • Implementation plans and timelines
    • Contract and pricing information
  • Implementation:
    • Onboarding guides and training materials
    • Technical support resources
    • User communities or forums
  • For each touchpoint, consider:
    • Preferred content formats (e.g., video, text, interactive)
    • Ideal channels (e.g., email, social media, in-person meetings)
    • Timing and frequency of interactions

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Step #12: Establish your unique value proposition(s).

“5 P’s” stage: Positioning

Your value proposition is the thing that makes you stand out in a crowded market. For enterprise accounts, it's crucial to position yourself as more than just a vendor: you're a strategic and empathetic partner for your customers. A strong value prop addresses each prospect's specific pain points, showcases your unique solution, and backs up claims with solid proof points. This step helps you clearly articulate why you're the best choice for your enterprise-sized prospects.

Here are some ways to tackle this step effectively:

• Clearly articulate what sets you apart in the enterprise space.
  • Identify your key differentiators, such as:
    • Unique features or capabilities of your product/service
    • Proprietary technology or methodologies
    • Specialized expertise or industry knowledge
    • Superior customer support or implementation processes
    • Flexibility or customization options
  • Focus on outcomes, not just features:
    • Quantify the impact of your solution (e.g., % increase in efficiency, $ saved)
    • Highlight long-term benefits and ROI
    • Emphasize scalability and future-proofing capabilities
• Use social proof to reinforce your claims:
  • Showcase relevant case studies and success stories
  • Highlight recognitions, awards, or industry rankings
  • Leverage testimonials from other enterprise clients
• Develop messaging that positions you as a strategic partner, not just a vendor.
  • Pivot focus from product features to business outcomes:
    • Align your messaging with the prospect's strategic goals
    • Discuss how your solution supports their long-term vision
    • Highlight your understanding of their industry challenges and trends
  • Emphasize your consultative approach:
    • Showcase your discovery process and needs assessment methodology
    • Highlight your ability to provide custom solutions, not one-size-fits-all
    • Demonstrate your commitment to ongoing optimization and improvement
  • Highlight your enterprise-level expertise:
    • Showcase your experience with similar large-scale implementations
    • Emphasize your understanding of complex organizational structures
    • Discuss your ability to navigate multi-stakeholder decision processes
  • Showcase your flexibility and scalability:
    • Highlight your ability to grow and adapt with their changing needs
    • Discuss your product roadmap and commitment to innovation
    • Emphasize your openness to feedback and continuous improvement
• When crafting your value proposition, try to address as many key elements as possible.
  • Key components include:
    • Problem statement: Clearly articulate the pain points you address.
    • Solution overview: How your product/service solves these problems.
    • Unique differentiators: What sets you apart from the competition.
    • Proof points: Case studies, testimonials, and hard data to back up your claims.
    • ROI statement: Quantifiable benefits and expected return on investment.
  • This will help “show” (rather than simply “tell”) a prospect why your product is the best option for them. 

Step #13: Craft your competitive positioning strategy.

“5 P’s” stage: Positioning

It's crucial to be aware of the competitive landscape in any sales situation – but particularly when prospecting enterprise-level accounts. This step involves gaining a deep awareness and understanding of your competitors, as well as where you stack up among them. By going through this effort, you'll be ready to effectively position your solution against alternatives. This preparation gives you confidence and credibility when engaging with prospects.

Here are some ways to tackle this step effectively:

• Use the results of your SWOT analysis to develop battle cards for key competitors in the enterprise space.
  • These battlecards should outline (at a minimum): 
    • Strengths and weaknesses of competitors;
    • How competitors position themselves, along with your counterpoints;
    • Key reasons why you win against them;
    • Feature comparisons;
    • Pricing and packaging differences; and,
    • Questions to highlight gaps for the buyer.
• Create diagrams to visualize where your product sits in the competitive landscape.
  • Utilize the 3-circle Venn diagram approach - a strategy popularized by Justin Michael (author of Tech-Powered Sales):
    • Define three key areas of differentiation or value
    • Place your solution and competitors within these overlapping circles
    • Highlight the unique space your solution occupies
  • Consider other visual tools:
    • Quadrant diagrams (similar to Gartner Magic Quadrant)
    • Capability vs. Price scatter plots
    • Feature heatmaps comparing multiple competitors
  • Ensure these visuals are:
    • Easy to understand at a glance
    • Backed by data or concrete examples
    • Tailored for different personas (e.g., technical, business, executive)
  • Use these visuals in sales presentations and leave-behind materials
• Prepare strategies for dealing with "no decision" or internal solutions.
  • Develop a strong case for change:
    • Quantify the cost of inaction or maintaining the status quo
    • Highlight risks of falling behind competitors who adopt new solutions
    • Show how your solution addresses future trends and challenges
  • For internal solutions:
    • Acknowledge the strengths of their current approach
    • Highlight the limitations and hidden costs of in-house solutions
    • Emphasize how your solution complements and enhances their existing investments
  • Create urgency:
    • Tie your solution to time-sensitive business goals or market opportunities
    • Offer time-limited incentives for early adoption
  • Address risk aversion:
    • When possible, offer pilot programs or phased implementations to reduce perceived risk
    • Highlight your track record of successful implementations
    • Provide clear ROI calculations and payback periods

Step #14: Going beyond features: position your brand as a problem solver.

“5 P’s” stage: Positioning

Positioning your brand as a problem solver shifts the focus from features to outcomes. This approach resonates strongly with enterprise buyers who are looking for solutions to complex challenges. By emphasizing how you improve the customer experience and deliver tangible benefits, you demonstrate your value beyond just being a product or service provider. This positioning helps you stand out in the crowded enterprise market.

Here are some ways to tackle this step effectively:

• Frame your offering as a solution to specific pain points, not just a product.
  • Create a pain point matrix:
    • List common challenges faced by your target personas
    • Map your solution's capabilities to each pain point
• Emphasize the outcomes and benefits, not just features.
  • Translate features into benefits:
    • For each feature, ask "So what?" to uncover the true benefit
    • Use benefit-driven language (e.g., "finish the day faster" rather than "automate budgeting")
  • Quantify the impact wherever possible:
    • Use metrics like time saved, cost reduced, or revenue increased
    • Develop objective tools like ROI calculators to show tangible value
  • Focus on both immediate and long-term benefits:
    • Highlight quick wins to build momentum
    • Showcase long-term strategic advantages
  • Use visual aids to illustrate benefits:
    • Create graphics comparing the "old way" vs. the "new way"
    • Develop before-and-after workflow diagrams
  • Incorporate benefits into your product demos:
    • Structure demos around solving specific problems rather than showcasing features
    • Use real-world scenarios to demonstrate how your solution delivers outcomes

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Step #15: Craft messaging tailored to each persona’s situation & industry.

“5 P’s” stage: Personalization

Tailored messaging is key to cutting through the noise in any prospecting scenario. By creating content that addresses your personas' specific pain points and priorities, you show that you understand their unique challenges. This step involves going beyond surface-level personalization to create truly resonant messages that address the prospect's individual situation, increasing the likelihood of engagement.

Here are some ways to tackle this step effectively:

• Create or curate content that speaks to industry- and role-specific pain points.
  • Develop a content matrix:
    • List all your personas on one axis
    • List common pain points or challenges on the other axis
    • Fill in the matrix with content ideas that address each intersection
  • Create role-specific whitepapers or eBooks:
    • Focus on challenges unique to each persona's role
    • Include industry statistics and trends relevant to their position
    • Offer practical solutions and best practices
  • Develop targeted case studies:
    • Showcase success stories featuring similar personas
    • Highlight metrics and outcomes that resonate with each role
  • Create persona-specific webinars or video content:
    • Host expert discussions on role-specific challenges
    • Offer practical tips and strategies tailored to each persona
  • Curate third-party content:
    • Share industry reports relevant to each persona
    • Compile lists of recommended reading for each role
  • Create persona-specific email nurture campaigns:
    • Develop a series of emails addressing common pain points
    • Offer valuable insights and tips specific to their role
  • Develop role-specific one-pagers or battle cards:
    • Summarize key pain points, solutions, and benefits for each persona
    • Include conversation starters and discovery questions
• Adjust your language and focus based on each persona's priorities.
  • Develop persona-specific glossaries:
    • List industry terms and jargon commonly used by each persona
    • Create a "translation guide" to help your team communicate effectively
  • Create messaging hierarchies for each persona:
    • Prioritize information based on what's most important to each role
    • Develop "elevator pitches" tailored to different attention spans
  • Adjust your communication style:
    • For C-level executives: Focus on strategic impact and high-level outcomes
    • For technical roles: Provide more detailed, feature-focused information
    • For end-users: Emphasize ease of use and day-to-day benefits
  • Tailor your call-to-action (CTA) for each persona:
    • Offer next steps that align with their decision-making authority
    • Provide resources that match their information needs
• Your messaging should go beyond surface-level personalization:
  • Common connections: Use LinkedIn Sales Navigator to find mutual connections between your company and prospects. These connections can open doors and build trust.
  • Prospect’s work history vs. your client list: Reference the prospect’s previous companies and showcase how you’ve helped similar organizations. For example, mention how you’ve solved a problem for their former employer.
  • Prospect-authored content: Engage with content the prospect has created. Comment on their posts or discuss points from their articles to show genuine interest.

• Different roles have different priorities. When crafting messaging, consider both job function and seniority.
  • A smart way to do this is by creating a messaging matrix. This message should target different roles – like Sales, Marketing, and RevOps, as well as various levels of seniority such as C-level, VP, and Director. This strategy helps your message resonate with each audience segment and makes it more effective.
    • Here’s how to think about tailoring your approach:
      • C-level executives: These are the visionaries, looking at the big picture. Talk to them about strategic alignment, long-term growth, and competitive advantages. They’re interested in how your solution supports company-wide initiatives and will be thinking in five-year increments.
      • VP-level executives: The VPs are the tacticians. They are focused on how to move the needle in the next three to six months. Highlight tactical improvements and resource optimization. Show them how your product can deliver measurable results and provide a return on investment in the short to medium term.
      • Directors and managers: Emphasize quick wins. Offer practical tools and support that help them succeed. This group, in particular, wants to make an impact now.
• Develop persona-specific objection handling:
  • Anticipate concerns specific to each role
  • Prepare tailored responses that address their unique perspective
• Tailor your value proposition to specific enterprise pain points:
  • Address common challenges like integration with legacy systems
  • Highlight compliance and security features
  • Showcase your ability to handle complex, large-scale implementations

Step #16: Plan individualized outreach strategies for each persona.

“5 P’s” stage: Personalization

Individualized outreach strategies ensure that you're approaching each persona in the most effective way. This step involves designing multi-touch, multi-channel sequences that cater to each target account's preferences. By preparing personalized scripts and templates, while leaving room for account-specific details, you create a scalable yet personalized approach to enterprise prospecting.

Here are some ways to tackle this step effectively:

• Design multi-touch, multi-channel sequences for each target account and prospect.
  • Create a comprehensive outreach plan:
    • Map out a 30, 60, or 90-day sequence for each persona
    • Include a mix of touchpoints across various channels (email, phone, social media, direct mail, etc.)
  • Develop a cadence that respects the prospect's time:
    • Space out touchpoints appropriately (e.g., 2-3 days between emails, 1-2 weeks between calls)
    • Increase or decrease frequency based on engagement signals
  • Tailor the channel mix to each persona's preferences:
    • Use LinkedIn for executive-level outreach
    • Leverage email for detailed information sharing
    • Use phone calls for personalized conversations
  • Plan content variety for each touchpoint:
    • Educational content (whitepapers, industry reports)
    • Social proof (case studies, testimonials)
    • Personalized insights or observations
    • Direct value offers (free assessments, consultations)
  • Incorporate trigger-based actions:
    • Plan follow-up steps based on specific prospect behaviors (e.g., email opens, content downloads)
    • Prepare alternative paths for different response scenarios
  • Use technology to support your sequences:
    • Leverage CRM and sales engagement platforms for automation and tracking
    • Set up alerts for important engagement signals
  • Plan for account-based marketing (ABM) coordination:
    • Align your outreach with broader marketing initiatives targeting the account
    • Coordinate timing of ads, direct mail, and personal outreach
• Leverage any existing connections or shared interests.
  • Identify shared connections:
    • Review each prospect’s LinkedIn profile, company website, and recent publications
    • Look for shared connections, alma maters, or professional associations
  • Develop a connection strategy:
    • Plan how to mention mutual connections in your outreach
    • Create tailored messaging for asking for introductions or referrals
  • Identify and leverage shared interests:
    • Look for common industry groups or professional organizations
    • Note any shared hobbies or personal interests mentioned in public profiles
  • Develop event-based outreach strategies:
    • Identify industry events or conferences you both might attend
    • Plan for pre-event and post-event outreach
  • Utilize company news or achievements:
    • Set up alerts for news about the prospect's company
    • Prepare templates for congratulatory messages or relevant insight

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Step #17: Use a multi-threaded approach to outreach.

“5 P’s” stage: Persistence

A multi-threaded approach is crucial in enterprise sales, where decisions involve multiple stakeholders. By identifying and engaging with multiple contacts across different departments and levels, you increase your chances of finding a champion and navigating the complex buying process. This strategy helps you build a stronger presence within the account and reduces the risk of your efforts stalling if one contact goes cold.

Here are some ways to tackle this step effectively:

• Identify multiple contact entry points.
  • Target at least 5-8 contacts across different departments and levels. Make sure to include C-level executives, VPs, directors, and managers in your outreach.
  • Use tools like LinkedIn Sales Navigator or DiscoverOrg to map out the organizational structure.
  • Focus on roles that are likely to be involved in or influenced by your solution:
    • Decision-makers: Those contacts with budget authority (e.g., CIO, CFO)
    • Influencers: Those contacts who can sway decisions (e.g., department heads, senior managers)
    • End-users: Those contacts who will directly interact with your solution (e.g., team leads, individual contributors)
    • Gatekeepers: Those contacts who control access to decision-makers (e.g., executive assistants)
  • Look for recent hires or role changes, as they might be more open to new solutions.
  • Consider targeting complementary departments. For example, if selling a marketing solution, include sales leadership in your outreach.
  • Create a relationship map showing connections between your target contacts.
  • Prioritize your contacts based on their likely influence in the buying process.
  • Regularly update your contact list as you learn more about the organization's structure and decision-making process.
• Leverage your network.
  • Use LinkedIn to find mutual connections. Ask connections for warm introductions whenever possible.
  • Thoroughly examine your LinkedIn network for second-degree connections at each target company.
  • Look beyond direct connections - consider alumni networks, professional associations, or industry groups you share with prospects.
  • When asking for introductions:
    • Clearly explain why you're interested in connecting with the prospect.
    • Provide a brief, compelling message that your connection can forward.
    • Offer to draft the introduction email to make it easier for your connection.
  • Use LinkedIn's "Get Introduced" feature to facilitate warm introductions.
  • Join relevant LinkedIn groups where your prospects are active and engage in discussions to build familiarity.
  • Attend industry events or webinars where you might encounter prospects or people connected to them.
  • Build relationships with industry influencers who might have connections to your target accounts.
  • Leverage your company's existing customer base for potential introductions or referrals.
  • Keep track of introductions and nurture these relationships, even if they don't immediately lead to sales opportunities.

Step #18: Develop an omnichannel outreach strategy. 

“5 P’s” stage: Persistence

An omnichannel strategy recognizes that different people prefer different communication methods. By planning touchpoints across various channels like email, phone, social media, and potentially direct mail or events, you increase your chances of connecting with prospects. This approach allows you to meet prospects where they are, adapting your outreach based on their engagement and preferences.

Here are some ways to tackle this step effectively:

• Leverage an omnichannel approach to outreach.
  • Remember, different people prefer different communication methods.
    • Plan touchpoints across email, phone, social media, and potentially direct mail or events. 
    • Prepare to pivot between channels based on prospects’ intent and behavior signals. For example, if the prospect doesn’t really pick up the phone, what other channels are they more active on?
  • Email:
    • Craft personalized, value-driven emails tailored to each persona
    • Use email tracking tools to monitor opens, clicks, and engagement
    • Develop a series of follow-up emails with varied content (e.g., case studies, whitepapers, industry insights)
  • Phone:
    • Prepare tailored scripts for cold calls and follow-ups
    • Use voicemail strategically, leaving concise, intriguing messages
    • Use AI-powered parallel dialers like Regie.ai to scale the volume of calls your team makes each day.
  • Social media:
    • Engage with prospects' content on LinkedIn (likes, comments, shares)
    • Use LinkedIn InMail for personalized outreach
    • Share relevant content and insights on Twitter or industry-specific platforms
    • Join and participate in LinkedIn groups where your prospects are active
  • Direct mail:
    • Send personalized, high-impact items to cut through digital noise
    • Consider dimensional mailers for key decision-makers
    • Leverage direct mail as a follow-up option to digital touchpoints
  • Events:
    • Attend industry conferences and trade shows where prospects gather
    • Host webinars or virtual events tailored to your target personas
    • Organize small, exclusive in-person events for high-value prospects
  • Video:
    • Create personalized video messages using tools like Vidyard or Loom
    • Develop short, educational video content relevant to each persona
  • Retargeting ads:
    • Use LinkedIn or Google ads to stay top-of-mind with prospects who've engaged with your content
  • Content syndication:
    • Distribute your content on platforms your prospects frequent
• Get your timings right.
  • Determine the best frequency and timing of outreach for each channel, based on industry benchmarks and your own prospects’ intent and behavior signals.
    • Email: Test different send times (e.g., early morning, lunch time, evening) to find what works best for your audience
    • Phone: Research suggests Wednesdays and Thursdays are often best for B2B calls, typically between 10 am and 4 pm. That said, you can also use behavior data signals to determine what times are best for specific prospects.
    • Social media: Use platform analytics to determine when your audience is most active
    • Direct mail: Time deliveries to arrive early in the week when decision-makers are more likely to be in the office
  • Create a balanced cadence:
    • Avoid overwhelming prospects with too many touchpoints in a short period
    • Space out your outreach across different channels (e.g., email on Monday, LinkedIn engagement on Wednesday, call on Friday)
  • Consider the prospect's time zone and work schedule
  • Be mindful of seasonal factors that might affect engagement (e.g., fiscal year-end, holiday seasons)
  • Use automation tools to schedule outreach at optimal times
  • Adapt your timing based on prospect behavior:
    • If a prospect consistently engages with your emails in the evening, adjust your send times accordingly
    • If you notice higher response rates to calls on certain days, prioritize those for future outreach
  • Set up alerts for trigger events (e.g., job changes, company news) to time your outreach strategically

Step #19: Implement a nurture strategy to ensure long-term engagement.

“5 P’s” stage: Persistence

Given how long sales cycles can be, having a strong nurture strategy in place is essential. This step involves planning how you'll keep prospects warm over extended periods, providing value even when you're not pushing for a sale. By establishing clear follow-up processes and using CRM tools effectively, you can maintain engagement and be ready to capitalize on opportunities as they come up.

Here are some ways to tackle this step effectively:

• Plan how you'll keep prospects warm over extended periods.
  • Develop a content calendar with regular, valuable touchpoints:
    • Share industry insights, trends, and thought leadership pieces
    • Offer exclusive research or reports relevant to their business
    • Provide updates on your product or service enhancements
  • Create a tiered engagement plan based on prospect value and stage in the sales cycle
  • Set up automated email drip campaigns with personalized content
  • Plan periodic check-ins or "health checks" to reassess their needs and timing
  • Offer free resources like webinars, workshops, or consultations (if possible)
  • Share case studies or success stories that align with the prospect's industry or challenges
  • Invite prospects to exclusive events or early access programs
• Prepare valuable touchpoints that don't always push for a sale.
  • Curate and share relevant third-party content (e.g, articles, videos, podcasts)
  • Offer free tools or templates that can help with their day-to-day work
  • Provide benchmark reports or industry comparisons
  • Share congratulatory messages for company milestones or achievements
  • Offer to make introductions to other professionals in your network
  • Share invitations to industry events or conferences
  • Provide educational content like how-to guides or best practice documents
• Design strategies for re-engaging prospects who go cold.
  • Create a "re-engagement" email sequence with fresh, high-value content
  • Use trigger events (e.g., company news, industry changes) as reasons to reach out
  • Offer a free assessment or consultation to reignite interest
  • Share new case studies or success stories relevant to their situation
  • Use multi-channel outreach (e.g., direct mail followed by a call) to grab attention
  • Consider offering a time-limited promotion or special terms (if possible)
  • Reach out with a new perspective on their challenge or opportunity
• If a prospect doesn’t engage after 10-14 days, it’s time to move on.
  • Swap them out for fresh contacts and continue iterating until you have a comprehensive report on each account that you’d be proud to present to your CRO.
  • Create a process for "retiring" unresponsive prospects:
    • Move them to a long-term nurture list
    • Reduce the frequency of outreach
    • Set a reminder to reassess in 3-6 months

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Final thoughts

Prospecting enterprise accounts isn’t for the faint of heart. It requires patience, persistence, and a strategic mindset. But for those who master it, the rewards can be transformative – both for your career and your company.

Remember, success in enterprise sales isn't just about closing a deal; it's about building long-term partnerships. Every interaction, every piece of research, every thoughtful follow-up is an investment in that relationship.

So, as you embark on your enterprise prospecting journey, keep these key principles in mind:

• Do your homework: Knowledge is your superpower.
• Build a network within the account: The more threads you add into the mix, the stronger your web will be.
• Provide value at every turn: Be a trusted advisor, not just a vendor.
• Be persistent (and patient): Enterprise deals are marathons, not sprints.
• Leverage technology wisely: Let it enhance, not replace, your human touch.

Now, armed with these insights and strategies, you're ready to take on the world of enterprise prospecting. It won't always be easy, but with the right approach, even the biggest whales in the business ocean are within your reach. So go forth, be bold, and happy hunting!

FAQs

Below, we've shared our answers to some of the most frequently asked questions (FAQs) we get about prospecting enterprise accounts. Here are the questions; find the one(s) you want to read about and click on the link to learn more:

• What defines an "enterprise" account"?
• What is the average enterprise sales deal size?
• How long does it take to close an enterprise deal?
• What’s the difference between SMB prospecting vs. enterprise prospecting?
• How do you find enterprise accounts to prospect?

What defines an "enterprise" account?

Let's make sure we know what we're looking for. Enterprise accounts aren't just big fish – they're whales. Though details may vary, here are some characteristics that enterprise organizations tend to have in common: 

• Size: These companies typically have 1,000+ employees.
• Revenue: We're talking annual revenue in the hundreds of millions or more.
• Complexity: They have multiple departments, each with its own decision-makers.
• Global presence: Often, these companies operate in multiple countries or regions.
• Buying process: Their purchasing decisions involve numerous stakeholders and longer sales cycles.

Think of companies like Microsoft, Amazon, or General Electric. That's the league we're playing in when we talk about enterprise accounts.

What is the average enterprise sales deal size?

The average deal size for enterprise sales can vary widely, but it’s typically significantly larger than SMB deals. While SMB sales might average around $4,000, enterprise deals often start around $50,000 and can go up to six or seven figures. The size depends on factors like the complexity of the solution and the scope of the implementation.

How long does it take to close an enterprise deal?

Enterprise sales cycles are generally pretty long, often taking several months to over a year. (It also isn’t unusual for enterprise deals to take multiple years to close.) The length of the sales cycle depends on a number of factors, including the complexity of the product, the number of stakeholders involved, and the internal processes of the organization. Patience and persistence are key, as these deals require multiple touchpoints and careful nurturing.

What’s the difference between SMB prospecting vs. enterprise prospecting?

Enterprise prospecting isn’t just SMB prospecting on steroids: it’s a completely different approach and requires an understanding of some key nuances. Here's a handy table to break down the most common differences between the two:

As you can see, prospecting an enterprise account is a whole different ball game. It's not just about scaling up your SMB approach – it requires a fundamental shift in strategy. 

How do you find enterprise accounts to prospect?

You want to ensure that the companies you’re targeting align with your ideal customer profile. Here are some strategies for finding enterprise accounts to go after: 

• Leverage LinkedIn Sales Navigator: As we've mentioned throughout this article, Sales Navigator can be a goldmine for finding enterprise accounts. Specifically, you can use the tool's advanced search filters in order to find companies that fit your target criteria, such as industry, company size, and geographic location. You can also pinpoint key decision-makers within these organizations to add to your prospecting list.
• Use industry reports & databases: Look into industry reports and databases like Gartner or Forrester; they can give you invaluable insights into which companies are leading in their sectors and might be in need of your solutions.
• Monitor market trends: Stay up to date on market trends and news. Companies that are expanding, acquiring new businesses, or launching new products are often ripe for prospecting. These activities indicate growth, which might lead to a need for your product or service.
• Use advanced AI sales solutions: Platforms like Regie.ai can help in identifying potential accounts by analyzing data and identifying companies that exhibit behaviors indicating a need for your solution. AI can also help in segmenting these accounts based on factors like size, industry, and potential fit.
• Network and referrals: Don’t underestimate the power of networking. It might feel old fashioned, but it works. Attend industry events, webinars, and join professional groups where you can connect with potential prospects or gain referrals to key contacts within enterprise organizations.

Remember, the quality of your prospecting list directly impacts the success of your outreach efforts. It’s about finding the right accounts that are most likely to benefit from what you offer.