Day 11 of 20 · AI for Sales
Follow-Up Sequences That Convert
⏱ 5 min
📊 Beginner
Here's a stat that should haunt every salesperson: 80% of sales require at least 5 follow-up touchpoints after the initial contact. But the average rep gives up after just 2. That's not a skill gap — it's a persistence gap. And it means most reps are abandoning deals that were going to close.
The reason is simple: follow-up is tedious. Drafting another email, leaving another voicemail, sending another LinkedIn message — each one requires thought, time, and emotional energy. After the second attempt with no response, it feels like you're bothering them.
AI removes the friction. Today you'll build multi-touch follow-up sequences that keep deals moving across channels — email, phone, LinkedIn, and value-add content — without being pushy and without eating up your day.
The follow-up math
Let's make the business case for persistence:
After 1 follow-up: 48% of salespeople never follow up. You're already ahead of half the competition.
After 2 follow-ups: 25% stop here. You're now ahead of 73% of reps.
After 3 follow-ups: Another 12% drop off. You're ahead of 85%.
After 5+ follow-ups: This is where 80% of deals close. Only 15% of reps make it here.
The math is clear. The reps who follow up consistently don't necessarily have better products, better pitches, or better territories. They just stay in the game longer than everyone else. AI makes it painless to be one of those reps.
Knowledge Check
Why do most sales reps stop following up after just 2 attempts?
A
Two follow-ups is generally considered sufficient in sales
B
Each follow-up requires time and emotional energy — after two non-responses, it feels like you're bothering the prospect, so reps give up
C
Most prospects explicitly ask reps to stop contacting them
D
Reps are too busy with new leads to follow up on existing ones
The emotional weight of non-response is real. After two emails with no reply, most reps tell themselves "they're not interested" or "I don't want to be annoying." But silence rarely means "no" — it means "I'm busy." The rep who sends follow-up #5 with genuine value often gets the reply that follow-up #2 never could.
The multi-touch sequence
A great follow-up sequence uses multiple channels and provides value at each touchpoint. Here's the framework:
Touchpoint 1 (Day 1) — Email: Recap your conversation, reinforce value, and propose a clear next step. This is your foundation.
Touchpoint 2 (Day 3) — Email: Short and casual. Reference your previous email. Add one new piece of value — a relevant article, a case study, or a data point.
Touchpoint 3 (Day 5) — LinkedIn: Comment on or share one of their posts. If they haven't posted recently, send a brief LinkedIn message. Different channel, different energy.
Touchpoint 4 (Day 7) — Call + Voicemail script: Call and leave a voicemail with a specific reason for the call. AI can draft the script.
Touchpoint 5 (Day 10) — Value-add email: Send something useful that has nothing to do with your product — an industry report, a relevant article, a connection introduction. Show you're thinking about them, not just your quota.
Touchpoint 6 (Day 14) — Breakup email: The "last email from me" that respects their time and often gets the highest response rate.
I had a great demo with Rachel Kim, Head of Marketing at a 200-person fintech company. She loved our analytics platform ($45K/year) but said she needs to "discuss with her team." It's been 24 hours with no reply to my thank-you email.
Build me a 6-touchpoint follow-up sequence across email, LinkedIn, and phone over 14 days. Each touchpoint should provide unique value — not just "checking in."
**Touchpoint 1 — Day 1 (Email) — Already sent** ✓
Your thank-you email. Good.
---
**Touchpoint 2 — Day 3 (Email)**
Subject: Thought this was relevant to your attribution challenge
Hi Rachel — I came across this report on multi-touch attribution for fintech companies [link]. Page 12 has some interesting benchmarks that relate to what you mentioned about proving marketing ROI to your CFO.
No pressure on our conversation — just thought this would be genuinely useful.
Best,
[Name]
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**Touchpoint 3 — Day 5 (LinkedIn)**
Connect with Rachel if you haven't already. Like or comment on her recent post with a thoughtful insight (not "Great post!"). Then send:
"Hi Rachel — enjoyed your post on [topic]. Separately, I put together a quick one-pager on how our platform would map to the attribution gaps you mentioned. Happy to share if it would help your internal conversations. No rush either way."
---
**Touchpoint 4 — Day 7 (Phone + Voicemail)**
"Hey Rachel, it's [Name] from [Company]. Quick call — I realized after our demo that I didn't show you the custom dashboard builder, which is actually what most marketing leaders use daily. Takes 2 minutes to show you. I'll shoot you a quick email with a screenshot. Talk soon."
Then send the email with the screenshot immediately after.
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**Touchpoint 5 — Day 10 (Value-add email)**
Subject: Intro to someone you should know
"Hi Rachel — this isn't about our platform. I was talking with [Name], Head of Marketing at [similar fintech company], and your challenges are remarkably similar. Would you be open to a quick intro? I think you'd both get a lot from a 15-minute chat.
Either way, I'm here if your team has questions about what we showed you."
---
**Touchpoint 6 — Day 14 (Breakup email)**
Subject: Should I close your file?
"Hi Rachel — I don't want to be the rep who clutters your inbox, so this will be my last follow-up unless I hear from you.
If the timing isn't right, no hard feelings at all. If something changes down the road, you know where to find me.
One last thought: the attribution gaps you described are costing your team roughly $15K/month in misallocated spend (based on the numbers you shared). If that's still a priority this quarter, I'd love to help. If not, I genuinely wish you and the team well.
Cheers,
[Name]"
---
Key principles: Every touchpoint adds value. No "just checking in." Channel variety keeps it fresh. The breakup email creates gentle urgency without pressure.
↻ Replay conversation
Knowledge Check
Why does the follow-up sequence use multiple channels instead of just email?
A
Prospects only check one channel at a time
B
Different channels reach people in different contexts — a LinkedIn message feels different from an email, and a voicemail adds a personal touch that text can't replicate
C
Using multiple channels makes you seem more professional
D
Email spam filters require you to use other channels
Rachel might delete your email while processing 50 others, but notice your thoughtful LinkedIn comment while scrolling during lunch. A voicemail with your actual voice creates a human connection that text can't. Multi-channel follow-up isn't about frequency — it's about meeting the prospect where they are, in the right context.
Timing strategies that work
When you send matters almost as much as what you send. Here are timing principles backed by response data:
Tuesday through Thursday are the highest-response days for B2B email. Monday inboxes are flooded, Friday minds are already on the weekend.
8-10 AM and 4-6 PM are the best windows. Early morning catches people planning their day. Late afternoon catches people winding down and clearing their inbox.
Never send at the top of the hour. Emails sent at 9:07 or 10:23 get higher open rates than those sent at 9:00 or 10:00 — they don't get buried in the flood of scheduled sends.
Space your touchpoints unevenly. Days 1, 3, 5, 7, 10, 14 feels natural. Days 1, 2, 3, 4, 5, 6 feels like stalking.
Ask AI to adjust your sequence timing based on these principles: "Rewrite my follow-up sequence with optimal send times for a [VP-level / Director-level] B2B prospect in the [EST / PST] time zone."
The multi-touch follow-up timeline — varied channels, increasing value, respectful spacing. Persistence without pushiness.
Scaling without losing the personal touch
The real power comes when you systematise this across your entire pipeline. If you're managing 30 active deals, that's potentially 180 follow-up touchpoints over the next two weeks. No human can write 180 personalised messages from scratch.
Here's the system: Build one master follow-up template for each deal stage (post-demo, post-proposal, post-negotiation). Then use AI to personalise each template for the specific prospect, referencing their name, company, pain points, and conversation details.
"Using this follow-up template, personalise it for [prospect name] at [company]. Reference their specific concern about [pain point] and our proposed solution of [solution]. Keep it under 100 words."
You stay strategic — deciding who to follow up with and when. AI handles the writing. Your pipeline moves faster, and every prospect feels like they're your only deal.
Knowledge Check
What's the best approach for managing follow-ups across 30+ active deals?
A
Only follow up with the top 5 deals and let the rest go
B
Build master templates for each deal stage and use AI to personalise each one for the specific prospect's situation — systematic but personal
C
Send the same follow-up email to everyone at the same time
D
Hire an assistant to handle all follow-ups
The system works because it separates strategy from execution. You decide the strategy — who to contact, when, and which channel. AI handles the execution — writing personalised messages that reference each prospect's specific situation. This scales your personal touch across your entire pipeline instead of forcing you to choose between quality and coverage.
💰
Day 11 Complete
"The difference between reps who hit quota and reps who miss it isn't talent — it's the follow-up touchpoints that 85% of salespeople never send."
Tomorrow — Day 12
Competitive Battlecards with AI
Tomorrow you'll build competitive battlecards that arm you with everything you need when a prospect mentions a competitor.