[Starter Kit] Step 2: Write Problem-First Messaging (That Gets Replies)

W/ 3 AI Prompts + 3 Templates

Your prospects don't care about you or your product.

They care about their broken processes, the 3am fire drills, and the manual work that eats 20 hours a week. When you lead with features, you're speaking a language they don't understand. When you lead with their pain, you're speaking their native tongue. The best cold messages don't sell, they educate on problems prospects didn't know they have or even realize they could solve.

Cold outreach isn't about you, it's about them.

Most outbound messaging fails because sellers pitch solutions

• Feature obsession: You dive straight into capabilities before establishing the pain (congrats, you sound like every other vendor in their inbox)

• Generic Fortune Cookies: You use pain points that could apply to any company ("saving time and money" isn't a pain point, it's a fortune cookie)

• The "All-in-One" Trap: You pitch yourself as a do-everything solution (translation: we do everything poorly instead of one thing exceptionally)

• Ignoring Digital Breadcrumbs: You miss the signals that reveal their actual problems (they just posted 5 DevOps roles but you're pitching cost savings?)

• One-Size-Fits-All Messaging: You forget that different personas care about different problems (the CFO doesn't care about developer experience)

Now that in Step 1 you've built your ICP, identified pain points, created mini-segments, and developed persona sheets, it's time to transform those insights into messaging that gets responses.

In this crucial early stage of outbound, testing is everything. One carefully crafted message that resonates is worth more than a thousand generic pitches.

Missed step 1? Read it here.

Today's menu:

• Part 1: The Kitchen Hierarchy: Who to reach out to first (and why it matters)

• Part 2: Digital Breadcrumbs: Turn account data into relevant messaging

• Part 3: The Buyer Journey Map: Know where they are in their decision process

• Part 4: Channel Adaptation Recipe: How to adapt your messages for email, LinkedIn, and calls

In the upcoming Step 3, we'll explore the technology stack to implement this approach efficiently.

P.S. Today I'm sharing how I'd approach outbound messaging if I were launching it for ElevenLabs, an AI voice platform I've been testing. This isn't what they currently use, it's my process for developing problem-first messaging for a new category by focusing on pain points around traditional voice production.

Let's get cooking!

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Part 1: The Kitchen Hierarchy (Who Gets VIP Treatment)

The foundation of successful outbound isn't crafting the perfect message, it's reaching out to the right people in the right order. In Part 1, we identified your ICP and built your target account list. But before blasting cold emails to everyone on that list, we need to prioritize.

Think of your prospects like diners at different tables in a restaurant. Some get the chef's special attention. Others get the standard menu. Your response rates depend on this hierarchy.

Why?

Because trust matters more than copy.

People (even within your perfect ICP) reply to those they already know 5x more often than to strangers. Starting with your warmest connections gives you the quickest wins and valuable feedback to refine your approach before scaling.

The 8-Table System (Closer Tables = Better Response)

Table 1: Your Personal Network (Response rate: 40-60%)

• Former colleagues, friends, and classmates

• They already trust you

• Message style: "Hey, been working on something perfect for [their pain]"

ElevenLabs Example:

"Hey Sarah, remember when you complained about voice actor costs at Coursera? Finally have a solution worth discussing."

Table 2: Second-Degree Connections (Response rate: 25-40%)

• Friends of friends on LinkedIn

• Mutual connections can vouch for you

• Message style: "Sarah suggested I reach out about [specific challenge]"

ElevenLabs Example:

"Mike mentioned you're struggling with voice consistency across Udemy's language courses. We just solved this for MasterClass."

Table 3: Investor Kitchen (Response rate: 20-35%)

• Your VCs' portfolio companies, and investors' networks

• Built-in credibility

• Message style: "[Investor] mentioned you're dealing with [pain point]"

ElevenLabs Example:

"Andreessen mentioned Duolingo's voice localization costs. We helped Babbel cut theirs by 80%."

Table 4: Happy Customer Referrals (Response rate: 30-45%)

• Your satisfied customers' network

• Social proof built in

• Message style: "Just helped [Customer] solve [exact same problem]"

ElevenLabs Example:

"Just helped Skillshare create consistent voices across 5 languages. They suggested you're facing similar challenges."

Table 5: Second-Chance Diners (Response rate: 15-25%)

• Previously closed-lost deals

• Past conversations that went cold

• Message style: "Things have changed since we last spoke..."

ElevenLabs Example:

"Last year voice cloning wasn't ready for education. Now Coursera uses it for 14 languages. Worth revisiting?"

Table 6: New Management (Response rate: 20-30%)

• Recent exec hires at target companies

• First 90 days = open to new solutions

• Message style: "Congrats on the new role - common challenge in first quarter is..."

ElevenLabs Example:

"Congrats on joining EdX! Most new Content VPs find voice localization is their biggest Q1 bottleneck."

Table 7: Local Kitchen (Response rate: 5-10%)

• Companies in your city/region

• Local connection adds trust

• Message style: "Fellow [City] company dealing with similar growth challenges"

ElevenLabs Example: "Fellow SF edtech company - noticed you're expanding to Spanish markets. Local happy to share how we helped Khan Academy."

Table 8: Cold Prospects (Response rate: 1-5%)

• No connection or relationship

• Requires maximum relevancy

• Message style: Must use multiple digital breadcrumbs

ElevenLabs Example:

"Noticed Udacity has 300+ English courses but only 10 in Spanish. Most platforms see 4x completion rates after voice localization..."

Other options (depending on your stage):

• Website visits if you have a tool to identify them or they have already given you their information. For example, if a prospect is on your newsletter, → every time they go on your website, you can see it. Better than contacting a cold prospect.

• LinkedIn visits or engagement with your company or LinkedIn profiles employees

CRM/MAP data

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Why this matters:

Warm introductions convert 5x better than cold outreach. Yet most teams spend 80% of time on cold prospects.

Fix your serving order, fix your response rates.

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Part 2: Digital Breadcrumbs (Using the Ingredients for Perfect Messaging)

Now that you know WHO to contact in what order, you need to figure out WHAT to say that will actually resonate. This is where your ICP research from Part 1 becomes actionable.

In Step 1, we identified your mini-segments based on shared characteristics. But to craft messages that truly stand out, we need to get even more specific by finding and leveraging those digital breadcrumbs, the trail of signals your prospects leave online.

Every prospect leaves a trail:

• Technology they use

• Content they create

• People they hire

• Problems they mention

• Etc.

These breadcrumbs do more than just help you identify targets.

They become the core ingredients of messages that feel personally crafted and immediately relevant.

In 2025, specific breadcrumb research is the main differentiator in outbound success. Generic messages get ignored, but messages that reference observable business signals cut through the noise.

Types of Digital Breadcrumbs (And What They Reveal)

This list varies by industry, but here are examples for ElevenLabs that you can adapt to your market (based on Step 1):

1. Tech Stack Breadcrumbs 🛠️

• What: Tools visible on their website/job posts

• Reveals: Integration pains, scaling challenges

ElevenLabs Example:

"Noticed you use Articulate Storyline for course creation but manual voice recording. That's usually a 3-week bottleneck."

2. Growth Breadcrumbs 📈

• What: Hiring patterns, funding news, expansion

• Reveals: Scaling pains, process breakdowns

ElevenLabs Example:

"Hiring 5 localization managers suggests you're entering new markets. Voice consistency across languages must be keeping you up at night."

3. Content Breadcrumbs 📝

• What: Course catalog, website content, product pages

• Reveals: Current limitations, missed opportunities

ElevenLabs Example:

"Noticed Masterclass has 180 courses in English but only 20 in Spanish. Classic voice talent bottleneck, we see this all the time."

4. Problem Breadcrumbs 🚨

• What: Support forums, review sites, job descriptions

• Reveals: Active pain points they're trying to fix

ElevenLabs Example:

"Your job posting for 'Voice Talent Coordinator' mentions managing 50+ freelancers. That overhead typically runs $300K+ annually."

5. Timing Breadcrumbs ⏰

• What: Quarterly reports, product launches, fiscal year

• Reveals: When they're most likely to buy

ElevenLabs Example:

"With Q4 approaching and your Spanish expansion announced, voice localization budget is probably top of mind."

Other breadcrumbs:

• ElevenLabs: SaaS company with presence in different markets + 1 person marketing team for DACH, but no video content in German

• B2B Solar Panels: Plants not using solar panels, with large roof sizes visible on Google Maps

The Breadcrumb-to-Message Recipe

Let's apply this to the specific ElevenLabs example:

Step 1: Gather your Ingredients (Find 3-5 breadcrumbs)

Company: [SaaS Company]

Breadcrumb 1: Offices in multiple markets including DACH region (or other market)
Breadcrumb 2: Only one marketing person for entire DACH region (or other market)
Breadcrumb 3: Website and product videos only available in English
Breadcrumb 4: Competitors in the space offer German content (or other language)
Breadcrumb 5: Recently announced DACH expansion initiative (or other market)

Step 2: Choose Your Main Ingredient (Pick the strongest signal)

• Freshest breadcrumb: DACH expansion initiative

• Most relevant pain: One-person marketing team but no German content

• Clearest connection: Resource constraint vs. market expectation

Step 3: Season with Context (Add supporting details)

• Industry benchmark: "Leading SaaS companies see 40% higher conversion with localized content"

• Peer example: "Zendesk increased DACH engagement by 65% after localizing videos"

• Quantified impact: "Solo marketers typically spend 15-20 hours per video on translation/voiceover"

Step 4: Serve While Hot (Time your outreach)

• Within 2 weeks of DACH expansion announcement

• Prior to quarterly planning (Q4 budgeting)

• When the DACH marketing position was recently filled

This highly specific combination of breadcrumbs tells a clear story: They're trying to expand in the German market but have set up their lone DACH marketer for failure by not providing localized content. This creates the perfect context for ElevenLabs' AI voice solution.

💡 AI Prompt: Digital Breadcrumb Hunt & Message Creator

Want to do this quicker?

This prompt does the research and writes for you: