Generic AI-written outreach gets ignored. “I noticed your company is doing great things...” - delete. Prospects can smell templated emails instantly.
The fix is not avoiding AI - it is using AI differently. Instead of generating emails, use AI to research deeply and craft personalization hooks. The result: emails that feel handwritten because the insights ARE personal.
Write a cold email to a VP of Sales about our CRM software.
Research and write a personalized cold email using this context: PROSPECT INFO: - Name: Sarah Chen, VP Sales at TechFlow (Series B, 80 employees) - Recent news: They just announced 40% YoY growth - LinkedIn: Posted about hiring 5 new SDRs last week - Company focus: Mid-market SaaS companies MY CONTEXT: - We help sales teams reduce ramp time for new hires by 50% - Our sweet spot: fast-growing teams adding SDRs quickly - Social proof: Similar company Acme reduced ramp from 90 to 45 days WRITE AN EMAIL THAT: 1. Opens with a specific observation about their growth/hiring 2. Connects their situation to a challenge we solve 3. Offers one piece of value (not a demo request) 4. Ends with a low-friction ask CONSTRAINTS: - Under 100 words - No buzzwords or "hope this finds you well" - Sound like a peer, not a salesperson
Research Phase
Great outreach starts with great research. Use AI to find signals that matter.
Research this prospect for cold outreach personalization: PROSPECT: - Name: [NAME] - Title: [TITLE] - Company: [COMPANY] - LinkedIn URL: [URL if available] FIND: 1. COMPANY SIGNALS - Recent funding, growth, or hiring announcements - New product launches or pivots - Leadership changes - Industry challenges they might face 2. PERSONAL SIGNALS - Recent LinkedIn posts or articles - Speaking engagements or podcasts - Career moves or promotions - Shared connections or interests 3. PAIN INDICATORS - Job postings that suggest challenges - Reviews (Glassdoor, G2) revealing issues - Tech stack that suggests opportunities - Competitor wins/losses OUTPUT: Top 3 personalization hooks I can use, ranked by relevance and specificity.
Pro Tip
Personalization Hooks
Not all personalization is equal. Here is the hierarchy from weakest to strongest:
Weak: Company-level generic
“I noticed TechFlow is in the SaaS space...” - Everyone knows this. Zero effort shown.
Medium: Recent company news
“Congrats on the Series B...” - Shows you did research, but same hook everyone uses.
Strong: Personal + relevant insight
“Your post about SDR ramp time resonated - we saw the same thing at [Company]...” - Shows you read their content AND connected it to your value.
Insight
Email Structure
The RHVA framework: Research-backed Hook, Value connection, and low-friction Ask.
Research
Hook
Value
Ask
Write a cold email using the RHVA framework: RESEARCH (what I learned): [Paste your research findings here] HOOK (personalization angle): [The specific observation you are leading with] VALUE CONNECTION: - Problem they likely have: [based on research] - How we help: [one sentence, no features] - Proof point: [similar company result] ASK (low-friction): [What is the smallest next step? Question, resource, quick chat] CONSTRAINTS: - Under 100 words (excluding subject line) - First line must grab attention - No "I" as the first word - No "hope you're well" or similar filler - Subject line under 5 words, creates curiosity OUTPUT: Subject line + email body + optional P.S. line
Multi-Touch Sequences
One email rarely works. A sequence of 4-6 touches, each adding new value, dramatically increases response rates.
Email 1 (Day 1): The Observation
Lead with personalization. Connect to a problem. Soft ask (reply with thoughts).
Email 2 (Day 3): The Value Add
Share something useful - article, benchmark, insight. No ask, just value.
Email 3 (Day 7): The Social Proof
Brief case study of similar company. Specific result. Soft ask.
Email 4 (Day 10): The Different Angle
New hook based on additional research. Different value prop. Direct ask.
Email 5 (Day 14): The Breakup
Acknowledge silence. Offer one last resource. Permission to close the loop.
Warning
Ready-to-Use Templates
Starting points for common scenarios. Always customize with real research.
Subject: Growth creates new problems [NAME], your Series [X] caught my eye. Scaling from [current] to [target] employees means your [TEAM] will face [SPECIFIC CHALLENGE we solve]. We helped [SIMILAR COMPANY] navigate that exact transition - they [SPECIFIC RESULT]. Worth a 10-minute chat to see if it applies? [YOUR NAME]
Subject: re: [topic of their post] [NAME], your post about [TOPIC] hit home. [One sentence agreeing or adding to their point with your own experience] We see this a lot with [THEIR TYPE OF COMPANY]. The ones who solve it fastest usually [INSIGHT CONNECTED TO YOUR VALUE]. Curious how you're approaching it at [COMPANY]? [YOUR NAME]
Subject: Noticed you're using [COMPETITOR] [NAME], I saw [COMPANY] is using [COMPETITOR]. No shade - they're solid for [USE CASE THEY'RE KNOWN FOR]. But teams at [SIMILAR COMPANY SIZE] often hit limits around [SPECIFIC PAIN POINT]. That's where we tend to help. Worth comparing notes? Happy to share how [SIMILAR COMPANY] made the switch. [YOUR NAME]
Next Steps
The framework is simple: research deeply, personalize specifically, ask softly. AskSmarter.ai can guide you through building sequences for your specific ICP.
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