Updated on: 24 January 2025

TL;DR: Chris Orlob's 5-Step SaaS Cold Email Framework

The Framework: A 5-step template used thousands of times that focuses on agitating pain rather than selling outcomes, with each sentence designed to get prospects to read the next one.

Quick Execution with ColdSend:

1. Step 1: Lead with "Looks like you..." (not "I noticed")
2. Step 2: Introduce the goal and conflict every buyer faces
3. Step 3: Spell out the lose-lose sacrifice: "You either get X without Y, or Y without X"
4. Step 4: Share social proof of desired outcome (no product mention)
5. Step 5: Easy CTA: "Up for a chat?" (not "Got 30 minutes?")

Key Results: Helped grow Gong from $200K to $200M ARR and $7.2B valuation. Framework designed specifically for SaaS sales where understanding buyer psychology trumps product features.

How to Copy Chris Orlob's SaaS Cold Email Framework: 5-Step Template Used Thousands of Times

Chris Orlob helped grow Gong from $200K to $200M ARR using proven cold email frameworks. Here's his exact 5-step SaaS template and advanced strategies, plus how to replicate them with ColdSend.

Who Is Chris Orlob?

Chris Orlob is the CEO of pclub.io and one of the most respected voices in B2B SaaS sales. His credentials speak for themselves: he helped grow Gong from $200,000 to $200 million in ARR and a $7.2 billion valuation in less than six years.

Background & Expertise: Former Head of Sales (Growth) at Gong, Chris has analyzed over 3,000 discovery call recordings and trained more than 10,000 SaaS salespeople through his platform pclub.io. His personal income grew from $36,000 to $1,639,000 during his journey—a testament to the frameworks he teaches.

Current Focus: Chris now runs pclub.io, the #1 skill transformation platform for revenue teams, and QuotaSignal. His content consistently attracts tens of thousands of sales professionals seeking to master the nuances of SaaS selling.

Why His Framework Matters: Unlike generic cold email advice, Chris's approach is specifically designed for complex B2B SaaS sales cycles where understanding buyer psychology is more important than product features.

The Revolutionary 5-Step Cold Email Template

Step 1: Lead with a Relevant Observation

The Rule: Use "Looks like you..." instead of "I noticed..."

Why It Works: "Language matters. Don't use the word 'I,' as in 'I noticed...' It's not about you. Sub that out for 'Looks like you...' That keeps the focus on them."

Example Opening:

• ❌ "I noticed you recently raised Series B funding..."
• ✅ "Looks like you recently closed your Series B..."

Step 2: Introduce the Goal and Conflict

The Framework: Every buyer has a desired outcome, but every desired outcome comes with a sacrifice.

Chris's Insight: "This is what makes this email template work. Every buyer is trying to achieve a desired outcome. But every desired outcome comes with a sacrifice. Articulate that."

SaaS Example: "As a VP of Sales scaling from 50 to 200 reps, you know firsthand how difficult it is to maintain deal quality while hitting aggressive growth targets."

Step 3: Spell Out the Pain in the Sacrifice

The Magic Formula: "It's a lose-lose. You either get X without Y, or Y without X."

Purpose: "Capture the pain your buyer feels from that 'conflict/sacrifice' better than they can themselves."

Template: "It's a lose-lose. You either hire fast and let weak performers slip through, or hire slow with rigorous standards but miss your headcount targets."

Step 4: Sell the Desired Outcome with Social Proof

Critical Rule: "Don't say a word about your product. Leave out the 'how.' Simply how you've helped others (that look like them) achieve a desired outcome that matters to them."

Example: "We've helped 47 VPs of Sales in high-growth SaaS companies reduce their sales hiring miss rate from 31% to single digits while hitting 100%+ of headcount targets."

Step 5: Make It Easy to Say "Yes"

The Psychology: "Don't lead with 'Got 30 minutes?' Your buyer: 'No, I don't, dude. I'm on zoom calls from sun up to sun down.' When you bring their limitation top of mind (their time), then that's the lens through which they'll make the decision."

The Solution: "Instead, 'up for a chat?' doesn't make the time investment explicit. Much easier to say yes to."

Perfect CTAs:

• "Up for a chat?"
• "Worth a conversation?"
• "Interested in hearing how?"

The Psychology Behind the Framework

Why 99% of Salespeople Get Cold Email Wrong

The Misconception: "99% of AEs and SDRs believe the secret to cold email is to sharpen the message and desired outcome. They're wrong."

The Reality: Chris explains that cold email isn't about outcomes, benefits, or positioning—it's about describing your buyer's problem so well it feels like you're "peering into their soul."

The Four Pillars of Elite Cold Emails

1. They Agitate Pain
"Step 1 in a successful cold email is to describe the PAIN better than the prospect can say it. That's not the same thing as promising an outcome. Cold buyers aren't thinking about outcomes (yet). They're thinking about the thorn in their side."

2. They Create a Compelling Chain of Sentences
"EVERY sentence you write in a cold email has one purpose: To get them to read the NEXT sentence. The only exception to this rule is the last sentence. If a sentence doesn't accomplish this, strike it. Pretend you get $100 for every word you remove. Get ruthless."

3. They Read Like Your Buyer's Journal
"As the buyer scans your email, the way you capture the pain should FEEL like a conversation they already have going on in their head. The 'best of the best' cold emails get this response: 'Damn, that puts words to something I've been struggling to articulate.'"

4. They Have an Easy-to-Say-Yes CTA
"The best cold emails are easy to say yes to. They don't ask for 30 minutes. That's hard to say yes to for any busy exec. They don't ask for time (explicitly). They simply reference the problem, and ask if it's worth having a conversation to explore fixing it."

Advanced Copy Strategies: Writing Like Your Buyer's Journal

The Buyer Psychology Insight

Chris discovered through analyzing thousands of sales conversations that successful cold emails mirror the internal dialogue already happening in the prospect's mind.

The Gold Standard Response: "Damn, that puts words to something I've been struggling to articulate."

Chris's Proven Templates in Action

Template 1: Quota Signal (Sales Hiring)

Hey Kevin,

Looks like you're hiring across the board in your revenue organization. Congrats.

Kevin, as a serial VP of Sales, having grown your company by 765%, you know firsthand how difficult it is to hit aggressive headcount targets without sacrificing your high bar for A+ talent.

It's a lose-lose. You either hire fast, hit your targets but let a few weak sellers sneak through, or hire slow, bring on strong account executives, but miss your hiring targets.

We've helped over 100 VPs of Sales in your industry decrease their miss rate on sales hires from 30% down to single digits.

Is eliminating sales miss hiring for this fiscal year worth a chat?

Template 2: Domo (Business Intelligence)

Hey Rachel,

Looks like Domo and Tableau are in a fierce competitive battle.

Rachel, as a seasoned business intelligence executive, you know firsthand that even though you have a better product, you can't rely on it alone to win competitive deals with Tableau.

Buyers will grind you down on price if your reps don't have bulletproof selling skills to beat Tableau in head-to-head demos.

We've helped BI companies like yours develop the competitive selling skills that win these horse races consistently.

Up for a chat about winning this competitive battle?

The Lose-Lose Formula That Converts

Chris's signature move is articulating the impossible choice every buyer faces:

Structure: "It's a lose-lose. You either [achieve goal A] with [negative consequence], or [achieve goal B] with [different negative consequence]."

Why It Works: This formula captures the exact frustration keeping your prospects up at night—better than they can articulate it themselves.

The 4-Sentence Cold Email Structure

Based on Chris's analysis of top-performing emails, here's his streamlined structure from his pclub.io methodology:

The Framework

Sentence 1: Context and trigger for reaching out
Sentences 2-3: The story (problem + solution narrative with social proof)
Sentence 4: Interest-based CTA
Bonus: P.S. with one-to-one personalization

Example Implementation

Subject: What happens if Ryan or Corinne leaves?

Hi Butler,

Looks like Ambition has been increasing headcount overall, but the engineering team has lost a few members.

With the average eng org experiencing 18% annual attrition, I'd imagine that retention might be top of mind. How are you empowering your managers like Corinne and Ryan to build a world-class engineering culture?

Sue from Apartment List has been leveraging Plato's mentorship community to help reduce attrition from 10% to 1%.

Interested in doing the same?

Best,
Florin

P.S. Congrats on being 1947 days sober today!

Why This Structure Works

Immediate Context: Opens with relevant observation that matters to them
Problem Agitation: Identifies the pain point without being pushy
Social Proof: Shows outcome achievement without explaining the "how"
Soft CTA: Makes it easy to say yes without time commitment

Chris Orlob's Complete Email Template Collection

Based on his 5-step framework, here are Chris's proven email templates for different SaaS scenarios:

Template 1: Sales Team Hiring (VP of Sales)

Subject: Hitting your Q2 hiring targets?

Hi [Name],

Looks like you're aggressively hiring across your revenue organization right now.

As a VP of Sales scaling from [current size] to [target size], you know firsthand how brutal it is to hit aggressive headcount targets without letting weak sellers slip through your screening process.

It's a lose-lose. You either hire fast and hit your targets but compromise on quality, or hire slow with rigorous standards but miss your hiring deadlines and quota goals.

We've helped 47 VPs of Sales decrease their miss-rate on sales hires from 30% down to single digits while meeting their hiring timeline targets.

Worth a quick chat about eliminating hiring misses this quarter?

Best,
[Your name]

Template 2: Product Marketing (SaaS Competitive Battle)

Subject: The Tableau problem

Hi [Name],

Looks like [Company] and Tableau are going head-to-head in several enterprise deals this quarter.

As a product marketing leader, you know that even though your product has superior capabilities, you can't rely on features alone to win competitive deals against incumbent solutions.

It's a lose-lose. You either win deals by competing on price (destroying margins), or you maintain pricing but lose deals to competitors with better competitive positioning.

We've helped product marketing teams at companies like Looker and Sisense develop competitive battle cards that increase win rates against Tableau by 40%.

Up for a chat about winning more competitive deals this quarter?

Best,
[Your name]

Template 3: Customer Success (Churn Prevention)

Subject: Your renewal rates

Hi [Name],

Looks like [Company] has been expanding rapidly - saw the Series C announcement. Congrats.

As Head of Customer Success during hypergrowth, you know that maintaining renewal rates becomes exponentially harder as you add customers faster than you can scale your CS team.

It's a lose-lose. You either assign CSMs to too many accounts (leading to churn), or you hire more CSMs faster than you can properly train them (also leading to churn).

We've helped CS teams at companies like Gainsight and ChurnZero maintain 95%+ renewal rates even during 3x growth phases.

Worth exploring how to scale CS without sacrificing renewal rates?

Best,
[Your name]

Template 4: Engineering Leadership (Technical Debt)

Subject: Feature velocity vs. technical debt

Hi [Name],

Looks like [Company] has been shipping features at an incredible pace based on your recent product announcements.

As an engineering leader, you're constantly balancing feature velocity to meet business demands with the need to address technical debt before it becomes unmanageable.

It's a lose-lose. You either prioritize new features to hit product deadlines but accumulate technical debt, or you focus on refactoring and infrastructure but miss critical product milestones.

We've helped engineering teams at companies like Stripe and Datadog maintain rapid feature velocity while reducing technical debt by 60%.

Interested in discussing how to balance both priorities effectively?

Best,
[Your name]

Template 5: Security/Compliance (Growth vs. Security)

Subject: SOC 2 compliance timeline

Hi [Name],

Looks like [Company] is preparing for SOC 2 compliance based on your recent security job postings.

As a security leader at a fast-growing SaaS company, you know the challenge of implementing robust security controls without slowing down your development teams' velocity.

It's a lose-lose. You either implement strict security measures that slow product development, or you maintain development speed but risk failing compliance audits.

We've helped security teams at companies like Slack and Zoom achieve SOC 2 compliance 40% faster while maintaining developer productivity.

Worth discussing an approach that doesn't sacrifice development velocity?

Best,
[Your name]

Subject Line Variations for Testing

- [Company] vs [Competitor] deals
- Your Q[X] hiring targets  
- The [pain point] problem
- [Specific metric] improvement
- [Department] scaling challenges
- [Current situation] update

Follow-up Sequence Templates

Follow-up #1 (3 days later):

Subject: Re: [Original subject]

Hi [Name],

Circling back on my note about [specific pain point].

Just helped [Similar Company] solve this exact challenge - they increased [specific metric] by [percentage] in [timeframe].

Still relevant for [Company]?

Best,
[Your name]

Follow-up #2 (1 week later):

Subject: [Industry] trend affecting [Company]

Hi [Name],

Saw this [Industry Report/News] about [relevant trend] affecting [their industry/company type].

Given [Company]'s focus on [specific area], curious how this is impacting your [relevant department/initiative]?

Worth a brief conversation about navigating these industry changes?

Best,
[Your name]

Personal Touch: P.S. shows you've done your homework

ColdSend Implementation for Chris's Framework

Why ColdSend Enables Chris's Strategy

Immediate Deployment: Chris's framework requires rapid testing and iteration. ColdSend's no-warmup infrastructure means you can start testing variations immediately instead of waiting 2-3 weeks.

Quality Focus Over Quantity: Chris emphasizes knowing your buyer deeply. ColdSend's flat-rate pricing lets you focus on crafting perfect emails rather than worrying about per-email costs.

Testing Infrastructure: "The hard part of this template? Knowing your buyer enough to make the 'fill in the blanks' resonate." ColdSend provides the infrastructure to test multiple buyer persona variations simultaneously.

ColdSend Setup for Chris's Framework

Basic Configuration:

• Plan: Starter Plan ($50/month) for 100 inboxes, 10K emails
• Volume: 100-200 emails per day for quality testing
• A/B Testing: 5-10 variations per buyer persona
• Follow-up: Single follow-up after 7 days maximum

Advanced Implementation:

• Inbox Segmentation: Different inboxes for different buyer personas
• Message Variants: Test Chris's 5-step framework against traditional approaches
• Reply Detection: Use smart categorization to identify interested prospects vs. negative replies

Performance Expectations

Chris's Benchmarks from SaaS Campaigns:

• Open Rates: 25-35% for personalized, relevant observations
• Reply Rates: 8-15% for well-crafted pain agitation
• Meeting Conversion: 60-70% of positive replies convert to meetings
• Quality Indicator: Responses like "This resonates" or "How did you know?"

ColdSend Advantages:

• Deliverability: High inbox placement maintains message integrity
• Speed to Market: Test framework variations within hours
• Cost Efficiency: Focus budget on research and personalization, not infrastructure

Subject Line Mastery: Less Is More

Chris's Subject Line Philosophy

From his comprehensive cold email guide: "The aim of the subject line is to get the recipient to open the email... Keep the subject line brief."

Subject Line Categories That Work:

1. Personalized Approach

• "Quick question about [Company Name]"
• "[Mutual Connection] suggested I reach out"
• "Thoughts on [Industry Trend]?"

2. Curiosity and Intrigue

• "This caught my attention"
• "Quick question"
• "Thought you'd find this interesting"

3. Direct Problem Reference

• "Scaling challenges at [Company]?"
• "[Industry] hiring in 2025"
• "Your [Department] growth"

What NOT to Do

Avoid These Subject Line Mistakes:

• Generic sales language ("Partnership opportunity")
• Overly clever wordplay that confuses
• ALL CAPS or excessive punctuation
• Misleading promises ("Your requested information")

Chris's Rule: "Include the benefit of opening the email" but keep it subtle and relevant to their specific situation.

Scaling with Testing and Optimization

Chris's Testing Methodology

The A/B Testing Framework:

1. Subject Line Testing: 3-5 variations per campaign
2. Opening Line Testing: "Looks like you..." vs. other approaches
3. Pain Articulation Testing: Different lose-lose scenarios
4. CTA Testing: "Up for a chat?" vs. other soft asks
5. Personalization Depth: Basic vs. deep research variations

Sample Size Requirements: Chris recommends at least 100 emails per variation before making decisions—manageable with ColdSend's infrastructure.

Advanced Personalization Strategies

The Research Hierarchy:

1. LinkedIn Activity: Recent posts, job changes, company news
2. Company Triggers: Funding, hiring, expansion, partnerships
3. Industry Events: Conferences, regulatory changes, market shifts
4. Personal Details: Education, interests, mutual connections

Chris's Personalization Rule: "Monitor your prospect's LinkedIn to find out one of their interests. Keep tabs on newsworthy events that may have affected a prospect or one of their competitors."

Performance Optimization

Key Metrics to Track:

• Open Rate by Subject Line Type: Identify highest-performing approaches
• Reply Sentiment: Positive vs. negative response ratios
• Meeting Conversion Rate: Percentage of replies that convert to calls
• Time to Response: How quickly prospects engage

Optimization Cycle: Test → Analyze → Refine → Scale winning variations

The Bottom Line: SaaS Cold Email Mastery

Chris Orlob's 5-step cold email framework helped grow Gong from $200K to $200M ARR because it operates on psychological principles rather than traditional sales tactics.

The Framework Works Because:

• Pain-First Approach: Addresses the "thorn in their side" before discussing solutions
• Buyer-Centric Language: "Looks like you..." keeps focus on their world, not yours
• Journal-Like Authenticity: Captures internal dialogue better than they can articulate
• Easy Commitment: "Up for a chat?" removes time pressure from decision-making

ColdSend Enables This Strategy by providing immediate deployment, high deliverability, and cost-effective testing infrastructure—letting you focus on Chris's sophisticated psychology instead of technical setup.

Implementation Requirements:

• Deep buyer research to make personalization resonate
• Willingness to test and iterate on pain articulation
• Focus on conversation quality over email quantity
• Patience to perfect the "lose-lose" problem framing

Ready to implement Chris Orlob's SaaS cold email framework? Try ColdSend and see how our infrastructure supports the sophisticated, research-heavy approach that drives real SaaS results.

Want to discuss implementing this framework for your specific SaaS market? Book a demo for personalized cold email strategy development.