30 Warm Paths Into One Account: How to Pick Three

Marcus is an enterprise AE. He opens his top account in the morning and sees 31 warm paths into it: colleagues, customers, two investors, an advisor, a partner.

It feels like good news. It isn't, yet.

Thirty-one paths is not a plan. If Marcus asks all of them, he burns goodwill across his whole company in a week. If he asks the first one on the list, he's guessing. What he needs is three, in the right order, each pointed at the right person.

Even a very well-covered account usually tops out at 30 to 40 paths across all four networks. Most accounts have far fewer. Either way the job is the same: cut the list down to the few asks most likely to become a meeting.

Here's the method, step by step.

Step 1: Drop the paper paths

Start by removing paths that only exist on paper.

• A shared employer ten years ago, with no evidence the two people ever worked together
• A LinkedIn connection with no messages, meetings or email between them
• A connector who has left your company, or a customer who has churned

These paths look like coverage and behave like cold outreach. Expect this step to remove a big share of the list, and don't feel bad about it.

Step 2: Point every path at a person who matters

A path is only useful if it ends at someone in the buying group. Map the paths that remain to the people they reach, then keep only the paths into people who matter for this deal:

• The economic buyer, who signs
• The champion, or the person most likely to become one
• The technical evaluator, who can kill the deal quietly
• A blocker you need to win over

Paths into people with no role in the decision come off the list, however strong they are. A great relationship with someone in another department is still a great relationship with the wrong person.

Step 3: Score what's left on four questions

For each remaining path, answer four questions. A simple 1 to 3 score per question is enough.

1. How strong is the relationship? Recent, frequent, two-way contact scores high. A friendly hello twice a year scores low. This is what a connector score measures.
2. Is the connection relevant? Did they work together on something close to what you sell? A former colleague from the same security team beats a college roommate.
3. Does the target respect this connector? An investor or former boss usually carries more weight than a peer from a different function.
4. What does the ask cost? If this connector was asked for an intro last week, or is a board member you only want to ask once a quarter, score lower. Protecting connectors from connector fatigue is part of choosing.

Add the scores. Sort the list.

Step 4: Pick three, one per job

Don't take the top three scores. Take the best path for each of three jobs:

• Path 1, the opener: the strongest path into the champion or the person who will take the first meeting.
• Path 2, the multiplier: the strongest path into the economic buyer, held until there's something to talk about.
• Path 3, the backup: the next-best path into the opener's target, through a different connector, ready if Path 1 doesn't land.

Three paths to three people from different networks is usually better than three paths to the same person. It's also how you avoid a single-threaded deal before it starts.

Step 5: Sequence them, don't send them all at once

Ask through Path 1 first. Give it about a week.

If it lands, use what you learn in the first meeting to shape the ask through Path 2. "Your VP of Security mentioned the audit next quarter" is a much better reason for an investor to introduce you to the CFO than "we'd love to connect."

If Path 1 doesn't land, close the loop with that connector and move to Path 3.

Sending all three asks on the same day feels efficient. It isn't. The target hears about you from three people at once, which reads as a campaign, not a referral.

A worked example

Here's what this looks like for a made-up account, Northwind Logistics, after steps 1 and 2 have cut 31 paths down to 7.

• Your VP of Engineering to Northwind's Head of Platform. Worked together for three years, still in touch. Strength 3, relevance 3, respect 3, cost 3. Total 12.
• Customer champion to Northwind's Head of Platform. Met at a conference last year. Strength 2, relevance 3, respect 2, cost 3. Total 10.
• Investor to Northwind's CFO. Sat on a board together. Strength 2, relevance 2, respect 3, cost 2. Total 9.
• Advisor to Northwind's CIO. Former boss. Strength 3, relevance 2, respect 3, cost 2. Total 10.
• Partner AE to Northwind's procurement lead. Closed a deal with them last quarter. Strength 3, relevance 2, respect 2, cost 3. Total 10.
• Your SDR to Northwind's Head of Platform. College friends, rarely in touch. Strength 1, relevance 1, respect 1, cost 3. Total 6.
• Your CFO to Northwind's CFO. Same CFO dinner group, met twice. Strength 1, relevance 2, respect 2, cost 3. Total 8.

The three picks:

• Opener: VP of Engineering to Head of Platform (12).
• Multiplier: advisor to CIO (10), held until after the first meeting. The CIO is the budget owner here, so the advisor's path beats the investor's even though the investor reaches the CFO.
• Backup: customer champion to Head of Platform (10), a different network into the same opener target.

The other four paths stay on the list. They're not wasted. They're next quarter's asks, or the paths to use if the buying group changes.

Doing this with AI

This method is easy to run by hand for one account and painful for fifty. It's also exactly the kind of work an AI agent is good at, as long as a human makes the final call.

If you've connected Boomerang to Claude or ChatGPT through the MCP server, a prompt like this does steps 1 to 4 in one go:

"Find every warm path into Northwind Logistics. Drop paths with no real interaction in the last two years. Map the rest to the buying group in our CRM. Score each on relationship strength, relevance, the connector's standing with the target, and how recently the connector was asked. Recommend an opener, a multiplier and a backup, each through a different connector, and explain why."

Inside Boomerang, Rudy does the same ranking for every target account automatically and drafts the ask for each pick in the connector's voice. Rudy never sends anything. The connector reads the draft and sends it from their own account.