Day 18 of 28 · AI Challenge
Sales and Outreach with AI
⏱ 7 min
📊 Beginner
Cold outreach has a terrible reputation — and honestly, most of it deserves that reputation. Generic "I hope this email finds you well" messages get deleted in seconds. The average cold email response rate is around 1-3%.
But personalized, well-researched outreach? That's a different story. Response rates of 15-25% are achievable when every email shows you've done your homework. The problem was always time — researching each prospect and writing a custom email took 20-30 minutes per person.
AI changes the math entirely. Today you'll learn to do that same research and personalization in 2-3 minutes per prospect.
The research-first approach
Bad cold outreach starts with what you want to sell. Good cold outreach starts with what they need to hear.
Before you write a single word, AI can research a prospect in seconds:
Company research — What does the company do? Recent news? Funding rounds? New product launches? Hiring patterns that signal growth or pain points?
Individual research — What has this person posted on LinkedIn? What topics do they care about? Did they recently get promoted, speak at an event, or publish an article?
Connection points — What do you have in common? Mutual connections, shared industries, similar challenges?
This research is what separates a 1% response rate from a 20% response rate. And AI does it in a fraction of the time.
Knowledge Check
Why does personalized outreach get dramatically higher response rates than generic emails?
A
Because personalized emails avoid spam filters better
B
Because personalized emails are longer and more detailed
C
Because the recipient can tell you actually researched them and have something relevant to say — it earns their attention
D
Because AI-written emails are always better than human-written ones
When someone sees that you've referenced their recent product launch or a challenge their industry faces, they know this isn't a mass blast. You've earned 10 seconds of attention. That's enough to make your pitch. Generic emails earn zero seconds — straight to trash.
AI-powered prospect research
Let's watch AI do the heavy lifting on prospect research. Say you're a marketing consultant trying to land small e-commerce brands as clients.
I'm reaching out to Sarah Chen, founder of GlowKit Skincare (D2C skincare brand). Before I write my cold email, help me research her:
1. What can we learn from GlowKit's website about their business?
2. What challenges might a D2C skincare brand with 10-50 employees face right now?
3. Find angles I can use to personalize my outreach (I'm a marketing consultant specializing in email marketing and retention)
Here's your research brief:
**GlowKit Skincare — Quick Profile:**
- D2C skincare, likely $1-5M revenue based on team size
- Probably spending heavily on paid acquisition (Facebook/Instagram ads)
- If they're like most D2C brands at this stage, customer acquisition cost is rising
**Pain Points for D2C Skincare Brands (10-50 employees):**
- Rising ad costs (Meta CPMs up 30% since 2023)
- Customer retention — skincare has high repeat potential but most brands don't capitalize on it
- Email list is probably undermonetized (industry average: email drives only 15-20% of revenue for brands this size, should be 30-40%)
- Likely no dedicated email/retention person on a team this small
**Personalization Angles:**
- Reference their specific products or recent launches
- Mention the rising-ad-cost problem (she's definitely feeling it)
- Position email marketing as a way to reduce dependence on paid ads
- If she's posted on LinkedIn about growth challenges, reference that
- Lead with a specific number: "Most skincare brands at your stage leave 20-30% of revenue on the table from email alone"
**Suggested hook:** Don't pitch your services. Instead, offer a free insight: "I looked at your email signup flow and spotted 3 quick wins that could boost your repeat purchase rate."
Want me to draft the cold email now?
↻ Replay conversation
Knowledge Check
In the research above, what makes the suggested hook effective?
A
It's short and easy to read
B
It offers specific, free value upfront instead of immediately pitching services — it shows competence and generosity
C
It mentions the prospect's name multiple times
D
It uses AI-generated buzzwords that sound professional
The hook works because it leads with value, not a sales pitch. "I spotted 3 quick wins" shows you've actually looked at their business. It's specific (not "I can help you grow"). And it's free — there's no risk in replying. This is the outreach formula that gets responses.
Writing the cold email
Now let's turn that research into an actual email. The best cold emails follow a simple formula: hook, relevance, value, ask.
Using the GlowKit research, write a cold email to Sarah Chen. Keep it under 120 words. My name is Alex, I'm a retention marketing consultant. My angle: I help D2C brands increase email revenue from 15% to 35%+ of total revenue.
**Subject: Quick thought on GlowKit's email revenue**
---
Hi Sarah,
I was looking at GlowKit's post-purchase flow and noticed you're probably leaving significant email revenue on the table — most D2C skincare brands at your stage drive 15-20% of revenue from email when it should be closer to 35-40%.
For a brand with your repeat-purchase potential (skincare customers buy 3-4x per year on average), that gap could mean an extra $15-30K per month you're not capturing.
I put together 3 specific changes to your email flows that could close that gap. Happy to share — no strings attached.
Worth a quick look?
Alex
---
**Word count: 107**
Key elements:
- Specific to her business (not a template)
- Leads with insight, not a pitch
- Concrete numbers ($15-30K/month)
- Low-friction ask ("worth a quick look?" not "book a 30-min call")
Now create 3 follow-up emails for days 3, 7, and 14 if she doesn't reply.
**Follow-up 1 (Day 3) — Subject: Re: Quick thought on GlowKit's email revenue**
Hi Sarah — just bumping this up. I know inboxes are chaotic.
The 3 email flow changes I mentioned are specific to skincare brands with your product lineup. One of them takes about 15 minutes to implement and typically adds 8-12% to repeat purchase rates.
Want me to send them over?
Alex
---
**Follow-up 2 (Day 7) — Subject: $15K question for GlowKit**
Hey Sarah,
I recently helped a D2C brand similar to GlowKit add $18K/month in email revenue by fixing three flows: welcome series, post-purchase, and win-back.
If that kind of result would move the needle for GlowKit, I'd love to share what I found looking at your setup. If the timing is off, no worries at all — just let me know.
Alex
---
**Follow-up 3 (Day 14) — Subject: Last one from me**
Hi Sarah — I'll keep this brief since this is my last follow-up.
If email retention is on GlowKit's radar for this quarter, I'd love to chat. If not, no hard feelings — I'm a big fan of what you're building.
Either way, cheers to the growth.
Alex
↻ Replay conversation
Knowledge Check
Why does the follow-up sequence decrease in pressure over time?
A
Because the prospect has already seen the pitch, so repeating it would be redundant
B
Because respectful persistence shows confidence — the final "last one from me" email respects their time and often gets the highest response rate
C
Because each email has fewer words
D
Because email algorithms favor shorter messages
The "breakup email" (last follow-up) often gets the highest response rate because it creates gentle urgency and shows respect. People who meant to reply but got busy will often respond when they realize they're about to lose the opportunity. Respectful persistence works — aggressive persistence doesn't.
Personalization at scale
The magic happens when you systematize this. Here's how to send 20 personalized cold emails per day in under an hour:
Step 1: Build a prospect list of 20 companies (LinkedIn Sales Navigator, industry directories, or manual research). Save names, companies, and one notable detail per person.
Step 2: Batch your research. Paste all 20 into AI: "For each prospect, identify their likely pain point and one specific personalization angle."
Step 3: Generate emails using your proven template as a base, with AI customizing the hook and value proposition for each prospect.
Step 4: Spend 30 seconds reviewing each email. Fix anything that feels off. Hit send.
20 prospects x $5,000 average deal value x 15% response rate x 25% close rate = $3,750 in pipeline per day of outreach. That's the math that makes this worth your time.
Final Check
What's the most important part of scaling cold outreach with AI?
A
Automating the entire process so it runs without any human involvement
B
Sending as many emails as possible — volume is everything
C
Using AI to write emails so you never have to review them
D
Using AI for research and drafting while you review every email for quality — scale without sacrificing personalization
AI handles the time-consuming parts — research, drafting, follow-up sequences — but you stay in the loop to ensure quality. Every email should pass the "would I be embarrassed if this prospect showed it to someone?" test. Scale the process, not the carelessness.
🎯
Day 18 Complete
"The best salespeople don't send more emails. They send better emails. AI lets you do both."
Tomorrow — Day 19
Financial Analysis Made Easy
Tomorrow you'll make AI crunch the numbers — budgets, forecasts, and profit analysis.