The Guide to Building an Enterprise Prospecting System

?: 24 min

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Enterprise accounts can make or break your pipeline, but cracking them requires a different playbook. Most resources barely scratch the surface, so I’ve created this guide to share strategies, templates, and tools that actually work, used by companies like Snowflake and Celonis.

Here’s what’s on the menu:

1. Why enterprise prospecting is different
2. The account-based approach
3. Cold Outreach Frameworks That Work
4. Key Performance Indicators (KPIs) and Goals
5. Templates, and AI Prompts
6. Resources

What resources you’ll get in today’s newsletter:

• Account Plan Template
• AI Prompts: For account plans, account research, and prospect research (using Perplexity or other AI tools).
• Cold Outreach Examples: Real emails and messages that booked meetings with enterprise execs.
• Tracking Template: For managing accounts and opportunities.

Let's get cooking!

The Enterprise Prospecting Playbook

1: Why Enterprise Prospecting is Different

Enterprise prospecting isn’t like targeting SMBs or mid-market accounts. It’s more complex and requires a different playbook. Here’s why:

Multiple Opportunities in One Account

Enterprise accounts are like ecosystems with endless potential.

• Opportunity Multiplication: One enterprise can have hundreds of opportunities across departments, business units, and regions.
• Decision-Making Complexity: Some enterprises centralize decisions, while others leave it up to individual teams or locations.
• Geographical Spread: Global operations mean different regions often have unique needs and challenges.

Key Insight: Reward SDRs for finding and pursuing multiple opportunities within a single account. This not only maximizes account value but keeps reps motivated.

Insight: According to a study by Gartner, the average number of stakeholders involved in a B2B enterprise purchase decision has increased from 5.4 to 6.8 in recent years

Executive Involvement in Outbound Efforts

In enterprise prospecting, the involvement of high-level executives is not just beneficial, it's often crucial:

• Multi-Level Engagement: From individual contributors to C-suite executives, everyone plays a role in outbound efforts
• Authentic Executive Communication: Executives often personalize outreach messages drafted by sales representatives to ensure authenticity and impact
• Strategic Outreach: High-level executives are typically asked to reach out to top accounts, as their involvement significantly increases the chances of success

I had a strategic BDR on my podcast who shared his email call-to-action: he asks to get an exec on the call for an executive-level conversation.

Cross-Team Collaboration

Winning enterprise accounts takes more than just sales, it’s a team effort:

• Team Size: Closing one big deal can involve 20–30 people from different teams.
• Collaboration: Sales, marketing (ABM, field), sales engineering, product, architects, and customer success all need to work together.
• Strategic Shift: Enterprise prospecting moves away from individual efforts to coordinated, strategic teamwork.

Strategic Account Selection, and prioritization

Account selection:

Choosing the right accounts is critical. Here’s what works:

• Leadership-Driven: GTM leaders, not individual reps, should decide which accounts to target.
• Data-Driven: Use data to identify accounts that fit your ICP. (More on improving ICP next week.)
• Resource Optimization: Targeting the wrong accounts wastes time, effort, and money, focus only on accounts that fit. And the enterprise team has a higher cost to run.

Here are 2 common mistakes I've seen at early-stage companies with enterprise prospecting:

• Confusing their TAM and ICP: Just because an account could buy doesn’t mean they will.
• Reps picking accounts: Reps shouldn’t waste time deciding who to target—leaders should provide a clear, curated list.

In Enterprise Outbound it's a common mistake to spend efforts and money on the wrong accounts:

Real Examples of Poor and Improved Account Selection

At Chili Piper:

• The Problem: We targeted “Enterprise” accounts with small GTM teams (e.g., 2,000 employees but only 20 reps), which weren’t truly enterprise-scale for our solution.
• The Fix: Narrowed the focus to accounts with 300+ GTM team members, ensuring better ROI for AEs and the business.

At Castordoc:

• The Problem: We wasted time on accounts transitioning from on-prem to data cloud solutions. They had great titles like our ICP but didn’t have the tools or problems we could solve.
• The Fix: Focused only on companies using a modern data stack, reducing the account list from 36k to 3k truly relevant accounts.

Data Point: Companies that excel at account selection see a 68% higher win rate, according to TOPO Research.

Account prioritization

Once you’ve selected the right accounts, prioritize them to focus on those with the highest potential.

Key Criteria:

• Strategic Initiatives: Look for accounts pursuing growth in areas where your solution can help.
• Revenue Potential: Rank accounts by potential deal size and lifetime value.
• Intent Signals: Use tools like Bombora and G2 to spot accounts researching solutions in your space.
• Likelihood to Close: Consider past engagement, existing relationships, or how well your solution fits their needs.
• Demo Requests: Prioritize enterprise accounts already reaching out for demos, they’re halfway there.

Example: Snowflake’s Approach to Account Prioritization

Snowflake uses intent data and analytics to prioritize accounts:

• ABM Intent Data: They leverage Bombora to identify accounts researching relevant topics.
• Scoring Model: Combines email clicks, website visits, and other data for a full view of buyer interest.
• Data Integration: They pull insights from tools like Mutiny, Bombora, RollWorks, and LinkedIn into their platform for deeper analysis.

Bottom Line: Picking and prioritizing the right accounts isn’t just smart, it’s essential for enterprise success.

2: The Account-Based Approach

The big mistake:

From coaching and shadowing sales teams, I’ve seen this pattern over and over: reps limit their prospecting to a single LinkedIn lead.

Most reps use a “prospect-based” strategy: they pick one person at an account, usually from a quick LinkedIn search, and hope for the best. While it feels fast, it leaves a ton of opportunities untapped.

Why this doesn’t work:

• Limited Insight: Focusing on one person means you miss critical pain points and context from the rest of the org.
• Multiple Stakeholders: B2B buying decisions involve a committee, not just one person. Ignoring this complexity can kill deals.
• Missed Opportunities: Accounts are ecosystems with champions, influencers, and budget owners. Reaching out to just one person limits your chances of finding the right entry point.

The Solution: The Account-Based Approach

Btw, this isn’t just for enterprise deals, it works for any segment. When you shift from targeting one prospect to thinking holistically about an entire account, you:

• Uncover more opportunities.
• Personalize your outreach with precision.
• Stand out from the noise.

Account-based messaging means focusing on the needs and challenges of the whole organization, not just one person. Yes, it takes more research and strategy, but it pays off.

Your “Recipe” for the Account-Based Approach

• Account Research
• Build Your “Point of View” (POV)
• Map Out Key Stakeholders
• Craft Tailored Messages for Different Levels
• Top-Down vs. Bottom-Up Approaches
• More Channels, More Touchpoints

Step-by-Step “Recipe” to Implement the Account-Based Approach

1. Account Research:

To win with enterprise accounts, you need to go deep. Understand their business model, goals, leadership, and tech stack. For public companies, dig into 10-Ks, earnings calls, and press releases to uncover growth strategies, initiatives, competitor insights, and financial details.

Real-Life Example: Deep Research in Action

Mark Roberge (Ex-CRO at Hubspost) shared on a podcast how top Enterprise AEs operate:

• They spend two months researching public company accounts before reaching out.
• They buy the prospect’s product, use the app, and create detailed reports.
• They send those reports to marketing execs, which helps them book meetings and close deals faster.

How Much Time Should You Spend?

Some SDR teams spend 2–3 hours per day on account research. Others dedicate Mondays to researching all accounts for the week.

The Goal of Account Research:

Find the strategic initiatives driving the account.

Examples of Strategic Initiatives:

• International expansion.
• Plans to go public (e.g., “I saw you’re preparing for an IPO…”).
• Press releases or 10-K details like product or market decline, or industry trends.
• New executive hires with relevant skills.

What to Look For:

• # of Employees and Potential Users: Size of their data or relevant teams.
• Revenue Model: How do they make money?
• Leadership Team: Who makes the decisions?
• Competitors & Similar Customers: Are they similar to accounts you’ve already won?
• Company History with You: Any prior interaction with your company?
• Tech Stack: What tools do they use? Can your product integrate with them?

The more you know, the better you can tailor your messaging. Take the time to understand their pain points, goals, and decision-making processes. It’s not just research, it’s your competitive edge.

Public Companies: How to Use 10-Ks, Annual Reports, and Earnings Calls

Public companies are required to share tons of useful info, if you know where to look. Here’s how to make the most of 10-K reports, annual reports, and earnings calls to stand out when prospecting:

• 10-K Reports & Annual Reports: Show the company’s financial health, growth strategies, competitors, business structure, and risks.
• Earnings Calls: Highlight recent performance and future priorities.

How to Find a 10-K

1. Go to Google and search for: Investor page [Company Name].

2. Navigate to the Financials or SEC Filings section.

3 Look for Annual Filings and download the 10-K as a PDF.

Focus on These 4 Key Sections (Skip the Rest):

1. Business Section:

• The company’s story: what they do, their industry, and how their business is structured.
• Essential for understanding the account before reaching out.

2. Risk Factors:

• Challenges and threats the company is trying to avoid.
• A great spot to identify problems your solution can help solve.

3. Management’s Discussion & Analysis (MD&A):

• The execs’ game plan: goals, competitors, expansion plans, and big investments.
• This is your gold mine for insight.

4. Financial Statements:

• Money in, money out, and overall financial health.
• Gives you an idea of how they’re performing and where they might invest.

Speed It Up with Keyword Searches

Don’t read all 100+ pages—use Ctrl/Command + F to search for specific terms.

• General keywords: risk, initiative, strategy, invest, growth
• Role-specific keywords: For Castor, I’d search for data, tool, cloud, analytics, technology.

Playbook Example:

For a company like Eventbrite, their 10-K report is 114 pages. Instead of wasting hours, focus on the sections and keywords that matter.

In just 15 minutes, you’ll have actionable insights for your account plan, and to craft a relevant outreach message and book meetings with top enterprise accounts.

10-K vs. 10-Q: What’s the Difference?

A 10-K is like a company’s yearly report card—it gives a detailed view of their performance and plans. But since it’s only released once a year, it might not include the latest updates, especially in fast-changing markets.

That’s where the 10-Q comes in. It’s a quarterly update that shows what’s happening right now.

Example: Eventbrite

• Their 10-K came out on 2/27/2024, outlining their big-picture plans.
• Their 10-Q, released on 11/07/2024, shows what’s currently happening.

You can see what they planned and how they’re actually performing today.

How to Prospect Private Companies

No 10-K? No problem. Use press releases, funding announcements, or leadership interviews to gather insights. But here’s a pro tip: a public competitor’s 10-K can be a goldmine.

A competitor’s 10-K reveals challenges, priorities, and strategies in the same market. Let’s be real, every company wants to outdo their competitors.

Here's how to do it:

1. Search for ”(Private Company Name) competitors” on Google or Perplexity.
2. Choose a couple of public competitors from the results.
3. Download their 10-K reports (these are often on the investor relations page of their website).
4. Look for key sections like “Risk Factors,” “Market Trends,” and “Strategic Initiatives.”

Now, use this insight to create a tailored outreach message. Here’s a template:

I noticed [Competitor] is expanding in the EMEA market and heavily investing in data tools. 

They also flagged concerns about [specific challenges, e.g., data security or scaling operations].

How are you approaching these trends?        

Use AI Tools to save time:

AI tools like Perplexity or ChatGPT can speed up enterprise account research. Why? Enterprise accounts have too much data online, it’s easy to get lost. AI helps you focus on the right information.

The biggest mistake with AI for research:

Most reps ask a basic question (like the one below) and stop there.

The Result?

You’ll get general info, like how the business is doing, but it’s often irrelevant to your solution or Point of View. You need to dig deeper to find actionable insights.

How to Get Better Results with AI:

Use specific prompts to guide your research (I share all the prompts in the section at the bottom). For example:

• Ask for details on their strategic goals.
• Look for challenges they’re facing that align with your solution.
• Identify key stakeholders and their priorities.

With tools like Perplexity, you can quickly get the relevant insights you need tailored to your outreach.

Here are a few examples of one company that I used to work at Castordoc, and one of my accounts was Evenbrite.

P.S. Looking for the prompts? I’ve shared them at the end of this newsletter.

Account plan for Eventbrite (Perplexity)

Earning calls for Eventbrite (Perplexity)

10k/10Q for Eventbrite (Perplexity)

Individual research results for the Head of data at Eventbrite

2. Build Your “Point of View” (POV):

Your POV is your take on what the account is trying to achieve and how you can help them get there. It’s the foundation of your outreach and one of the most underrated steps.

How to Build Your POV

1. Based on Your Research:

• What strategic moves are they making?
• What goals are they trying to reach?
• What challenges are holding them back?

2. Connect the Dots:

• How can your product help them hit their goals faster or more cost-effectively?
• How can you solve their problems?
• What’s the compelling reason to act now?
• Which customer success story can you share to build credibility?

Use AI tools to help analyze account data and refine your POV faster.

3. Map Out Key Stakeholders:

Figure out who’s involved in the decision-making process and what they care about.

Here’s who to focus on:

• Above the Line (C-level Execs, VPs): The decision-makers who control the budget. For above-the-line prospects, I like using their website to map out the C-level team. It’s often faster than digging through LinkedIn.
• Below the Line (Directors, Managers): Influencers who shape decisions and understand the team’s needs.
• End-Users (Individual Contributors): The people who’ll use your product and can share real-world pain points.

Each group cares about different things, tailor your messaging accordingly.

4. Craft Tailored Messages for Different Levels:

Your messaging should align with the priorities of each stakeholder. Here’s how to tailor it:

Above the Line (ATL): C-Level Execs and VPs

Focus On:

• Strategic initiatives
• Long-term vision
• Business impact and ROI

Example for a Chief Data Officer:

• Improve decision-making processes.
• Build trust in data across the organization.
• Transform the data team into a profit center, not a cost center.
• Drive data democratization.

C-level execs care about the big picture, how you’ll help them achieve long-term goals and make a real impact on the business.

Below the Line (BTL): Directors, Managers, and End-Users

Focus On:

• Day-to-day operations.
• Practical solutions.
• Efficiency and productivity gains.

Examples for Data Roles:

Data Engineering Manager:

• Speed up hiring with a central hub for KPI definitions and datasets.
• Boost team productivity by cutting data search times from hours to minutes.

Data Engineer:

• Reduce manual work for impact analysis.
• Get projects done faster with a single tool for datasets and context.
• Spend less time on tedious documentation.

BTL and end-users care about solving their daily challenges and getting work done faster and easier.

Make sure your message speaks directly to the person’s role and priorities: big picture for ATL, practical wins for BTL.

5. Top-Down vs. Bottom-Up Approaches:

When reaching out to enterprise accounts, you can take two paths:

• Top-Down Approach
• Bottom-Up Approach

Top-Down Approach

Start at the top with VP/C-level execs and work your way down if they don’t respond.

Why it works: It’s quick and can get you referrals directly to the right person.

Bottom-Up Approach

Start with individual contributors (end-users), then use their insights to move up to managers, directors, and finally execs.

Why it works: It takes longer but gives you insider knowledge, better-quality opportunities and you might build champions at the same time.

How to Implement the Bottom-Up Approach

Learned this from KD (Kevin Dorsey):

Step 1: Start with End-Users

Your goal here is simple: find out if the problem you solve actually exists. End-users often reveal “hidden” pain points that don’t show up on the surface.

• Building relationships with end-users creates mutual connections with decision-makers.
• Instead of 0 mutual connections, decision-makers will see you already have 30+.
• It’s easier to get responses from end-users since they’re more accessible.

Example Template (from KD):

Subject Line: Quick Question

“Hey [Name], I was thinking of reaching out to [VP Name] but didn’t want to waste their time. Do you all even have/do/work with [problem/solution]?”        

Here’s a real example used by Florin Tatulea:

Hi {{first_name}},

I was going to reach out to [VP Name], but I wanted to get my facts straight first. Most HR teams I speak with run 1–2 comp/merit review cycles per year.

How is your team managing those cycles? Are they still done manually in spreadsheets?

We’ve built a system to help manage salary bands, cut comp cycle time by 80%, and give managers better data to make fair and informed decisions.

Think this could help?        

Step 2: Move to Middle Managers

Once you’ve gathered insights from end-users, use this to reach out to managers or senior managers.

Why This Works:

• Managers often know if there’s a problem and whether they’re trying to fix it.
• This is where you connect the dots between what you’ve learned and potential solutions.

Example Template (from KD):

Subject Line: Spoke with [End-User Name]

“Hi [Manager Name],

I spoke with [End-User Name] and learned your team is experiencing [specific issue].

Most [role-specific leaders] I work with deal with [common pain point] and often solve it by [solution]. Have you thought about exploring options to [specific benefit]?        

Real examples from Florin Tatulea:

Subject Line: Spoke with Lisa

Hi [James],

Lisa mentioned you’re already using salary benchmark surveys (e.g., Radford/Pearl Meyer) and have pay bands set up internally.

Most TR leaders I talk to juggle multiple systems for benchmarking, bands, comp reviews, and total rewards communication. Have you considered unifying these workflows to get better data and save costs?

Let me know if this is worth exploring as you plan for 2024.

Best,        

Step 3: Reach the Execs

With insights from managers, it’s time to approach directors, VPs, or C-level executives.

Why This Works:

• You’ve already done your homework, so you can show them what’s happening in their team.
• This positions you as someone who understands their challenges and can provide real solutions.

Here’s his template:

Hi [Exec Name],

I’ve spoken with [Manager A], [Manager B], and [Manager C]. It seems there’s no routing tool in place, which means leads aren’t going to the right people.

You’re handling 500 leads a month. Even with a conservative 10% lift in conversions by routing leads to your best reps, you could add [$X million] in pipeline.

Can I show you how easy this switch could be?        

By starting at the bottom and working your way up, you gather valuable insights and build credibility at each level. By the time you reach the execs, you’re not just another cold email, you’re someone who knows their team and their challenges.

Real-World Feedback about the bottom-up approach

A CRO shared:

Another story from a VP at Snowflake:

Why Use Both Approaches?

• Top-Down is faster and helps you get referrals.
• Bottom-Up gives you rich insights and helps you craft more targeted messaging.

Generally, top enterprise teams, use the Top-Down approach first, then Bottom-up if top-down doesn’t work.

6. More Channels, More Touchpoints:

For bigger deals (higher ACV and LTV), you can go beyond emails, LinkedIn, and cold calls. With higher value targets, you can afford a more resource-heavy approach.

Here are some extra channels to try:

• In-Office Visits
• Trade Shows
• Conferences
• Gifts
• Personalized Websites: Tailored to the industry, account, or even individual prospects.

Examples of personalized websites

1. Industry-Level Personalization

Example: Snowflake

In this outbound example, Snowflake personalizes content at the industry level with two simple touches:

• Headline: Tailored to common industry pain points.
• Image: Aligned with the industry.

Personalization doesn’t need to be complicated. The key is showing you understand your prospect’s goals and challenges.

Why it works: Snowflake’s account-level personalized pages have a meeting rate 4x higher than non-personalized pages.

2. Account-Level Personalization

Example: Snowflake

Adding a company name is step one, but great personalization goes beyond that. Snowflake’s approach includes:

A personalized note from a sales rep highlighting:

• Why this matters to the account.
• Why they should care.
• What’s in it for them.

A curated block of relevant content (e.g., blogs, eBooks, reports). Think Netflix: the content isn’t created for one person, but it’s curated to match their interests.

Example: Mutiny

Mutiny builds microsites tailored for target accounts, showcasing content and messaging specific to each account’s challenges.

• They map CRM and account data to dynamically create these sites at scale (no manual work for each page).
• Microsites feel bespoke, saving time and resources while delivering hyper-relevant experiences.
• Prospects are sent these personalized URLs in cold outreach.

3. Prospect-Level Personalization

Snowflake creates pages focused on individual prospects, supported by one-to-one targeted ads and personalized mail. These pages include:

• Headlines: Addressing specific pain points.
• Subhead Copy: Agitating the prospect’s unique challenges.
• Occasionally, the person’s name (but not always).

Pro Tip: Avoid being creepy. It’s like buying flowers for someone who loves blue roses instead of saying, “I know you love blue roses.” Subtle, thoughtful personalization wins.

Using Account Plans

In enterprise sales, account plans aren’t “one size fits all.” You don’t need them for every account, but for strategic accounts, they’re a must. Whether they’re existing customers or prospects, your plan should include:

• White Space Analysis: Where are the opportunities?
• Specific Details: Tailored strategies for each account.

But what’s an account plan or what’s the definition of “Account planning”?

What’s an Account Plan?

It’s a living, breathing document that keeps your team on the same page about an account. It includes details on the account’s strategy, challenges, decision-makers, and the actions you’ll take to win and grow the business.

Gartner’s Definition:

“Account planning is the process of mapping out important details about a new prospect or existing customer, including information about their decision-making process, the companies you're competing with to close them and the overall strategy to win them over, retain and grow them.”

Pillars of a Great Account Plan:

1. Account Research:

Links, 10-K reports, website info, org charts, previous meeting notes, and assets that reveal what’s happening under the hood.

2. Prospect Research:

Key stakeholders, their roles, and what matters most to them.

3. Your Point of View:

Based on the research, form hypotheses about where you can help. What initiatives are they pushing? Where do you fit?

4. Action Items:

Concrete next steps—reaching out, scheduling a demo, sending collateral, or attending their upcoming conference.

I’ve added a template for you at the end of the newsletter.

3: Framework: Cold Outreach That Gets Results

Do the Math

This framework cuts through the noise by showing a deep, personalized understanding of the prospect’s business, something most generic emails miss.

I’ve used this at Castor myself, and I’ll show you 3 ways I’ve applied it.

The framework follows this structure:

1. What You Know About Them: Personalize based on specific insights about their business or role.
2. How You Help: Clearly explain how your solution ties to their needs.
3. Do the Math: Show the potential impact (e.g., ROI, time saved, revenue generated).
4. Call to Action: End with a simple, direct next step.

Here’s an example email following this approach:

Want the full playbook? The rest of this playbook goes deeper into exact templates, AI prompts, and tools I’ve used (along with other Enterprise GTM teams) to book meetings with execs at top enterprise accounts.

What you’ll get as a Subscriber:

• Real cold email examples that actually worked.
• Enterprise prospecting benchmarks.
• AI research prompts to save time and get results.
• Downloadable account plans and tracking templates.

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