AI-assisted personalized outreach, outbound sequences, and sales message drafting

AI made me faster at sales.
That turned out to be the least interesting part.

I work in business development, and I use AI almost every day for:
• Researching accounts
• Preparing for calls
• Writing outreach
• Summarising conversations
• Following up with prospects

Sometimes it gives me something genuinely useful.
Other times, it gives me a perfectly written email that I would never send.

The difference is usually context.

AI on its own doesn’t know:
• Someone from our team spoke to the company six months ago
• What the prospect cared about
• Why the conversation stopped
• What has changed since then
• Whether there’s a genuine reason to reconnect now

But when I started using AI alongside HubSpot and the other tools in my workflow, the picture became much clearer.

AI helps me work faster.
The context helps me decide who is worth contacting, what might matter to them and whether I have something relevant to say.

That distinction matters because my manager, Joshua Mathew, is not measuring success by the number of emails AI helps me produce.

It's more about whether those emails lead to conversations, meetings and qualified opportunities.

That’s why the thinking behind HubSpot’s new Agentic Customer Platform clicked for me.

It isn’t simply about adding another AI tool.
It’s about bringing customer data, business context, people and AI agents together, so the AI working with me knows more than what I typed into a prompt.

I work at HubSpot, so of course I’m biased.

But from my view:
AI without context can make us look busier.
AI with context has a much better chance of making us useful.

Has AI improved actual outcomes for your team yet, or mainly increased output?

Also, with Spider-Man all over my personal feed lately, this meme felt pretty apt.

The more I use AI in sales, the less I worry about it replacing me.
Today I was doing my usual B2B work: looking for new clients, checking companies, updating CRM, writing emails. AI was there for most of it. Research, drafts, summaries, ideas. Things that used to take hours now take minutes.

And I love that. I have absolutely no nostalgia for spending three hours doing something AI can now do in ten minutes. 
After 20+ years in B2B sales, I’ve learned that people come back when they trust you and know they can rely on you. No perfect email or presentation can replace that.
Relationships are still built over a cup of coffee. Or, in Finland, sometimes in the sauna 😅
AI can make me faster, better prepared, and probably more organized than I naturally deserve to be.
But it can’t build 20 years of reputation for me!
And strangely enough, the more AI we have around us, the more I think we start to value something very old-fashioned: a real conversation with another human being.
So no, I’m not afraid of AI replacing me.

And you? Are you worried that AI might replace you one day?.

If I was given a leads list to reach out to I would use AI to write my personalized outreach to each and every one of them and here’s how I would do it.

First I would make sure it knows absolutely everything about me. I would act like I was writing a book about my life and tell it every story I can remember in as much detail as possible.

That’s a heavy lift up front that you won’t ever have to do again that will pay you royalties over time.

Then I would drop this prompt in there. “I am going to drop a list of people into the chat. I want you to thoroughly research each individual to find something in one or all three of the following categories, common people we are connected to, common or similar experiences we’ve shared, common or similar interests we have. Prioritize the search by people, experiences, then interests. If nothing can be found then I want you to search their companies information for recent and relevant content that I can relate to. If nothing can be found there, then I want you to find something recent and relevant in their industry that I can relate to and share with them. Write a quick message for each person based on that frame work that immediately draws the parallels for us and asks for nothing other than a conversation with them.”

Then drop the list into the chat and watch the magic happen.

Everyday review as many of the messages as you have time for. Tweak the messaging to make it perfect for yourself.

Then open up Vidyard and shoot the message in a video.

Drop the video into an email and hit send.

You don’t have to comment on this post for me to send you something.

You don’t have to schedule a call with me to talk about it more.

Follow steps 1-3 and magic, your response rates sky rocket.

I’m giving this away because I’m sick of how bad the sales profession has gotten and just want to be approached like a real human.

Oh, and if I didn’t have a leads list I would make one by searching on LinkedIn for “business leaders in ________ (fill in your local area)”, then do steps 1 through 3.

Business development has never been simpler with these 3 tools combined.

Do it for all the business owners out there. They will thank you.
__________________________________________
If you are in sales or leadership and looking for more ways to drive performance, ♻️ connect with me and let’s 🗣️ talk about it.

I have a Google Sheet that fills up with new leads whenever they come in for our product. I run a separate chat connected to Bright Data for search, Google Sheets, and Gmail. It looks up extra information on each lead, fills in the missing fields, and drafts a personalized email saved directly into Gmail.

Not long ago I’d have done a good chunk of this by hand. Now I hand over most of the clicking to AI. I still read every draft before it goes out and sometimes do adjustments. Nothing sends without me.

If you use Claude from Anthropic, add Apollo as a connector and do real Apollo work without leaving the chat.

In one conversation, you can:
- Find prospects using natural language
- Enrich people or companies
- Create or update contacts
- Draft and send one-off emails
- Create sequences, improve steps, and generate variants
- Add contacts to an existing sequence
- Create and manage tasks
- Analyze your team's performance

My outbound activity is up over 500%. My cold call volume is up over 1,200%. And I haven't added a single hour to my week.

Notion hasn't changed how I sell — but it's completely changed how I spend my time.

The hours I used to spend reading the news, scanning alerts, and trying to turn it all into something I could actually tie to Notion's value and bring into prospect conversations? Most of that happens now while I'm asleep.

In this video I walk through one of the many automated workflows I've built for myself and run every single day.

It scans all 75 accounts in my book of business, surfaces the breaking news and hot topics for specific accounts, and flags the persistent themes showing up across all of them — the shared challenges I can build a real point of view around. Then it takes that POV and automatically drafts targeted cold outreach against it.

All before I wake up.

Since I rolled this out at the start of May, that jump in activity has directly sourced more than $300K in new pipeline — not because I'm working more hours, but because the prep and the POV building are already done before I sit down.

I get to spend my time on the part that actually closes deals — the conversations.

If you're a sales leader and you want to learn how to replicate workflows like this for you or your team, comment "Custom Agent" below and I'll reach out — or just DM me directly.

2 months ago, if you had asked me how long I spend researching prospects and writing personalized outbound emails…

I would’ve said:
“Too long.”

20 to 25 minutes per prospect.

Reading LinkedIn profiles.
Understanding company context.
Finding triggers.
Writing relevant emails.
Figuring out who else in the org to target.
Planning follow-ups.

It was effective.
But painfully manual.

So I built something for myself.

Today, I can generate:

• ICP-calibrated prospect intelligence
• personalized outreach angles
• 5-email sequences
• LinkedIn messaging strategies
• stakeholder mapping
• follow-up paths if someone ghosts
• qualification + scoring

…in under 5 minutes per account.

What used to take me hours now happens before my coffee cools down ☕

And the outcome?

Q1: 146% achieved.

That’s when I realized this wasn’t just a personal workflow hack.

It could help other sales teams too.

So I turned it into:
Impact Prospect Intelligence

An AI-powered prospect scoring + outbound intelligence system calibrated to your exact ICP.

If you want access to the trial version, comment:
IMPACT

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#Sales #B2BSales #OutboundSales #Prospecting #AI #SalesAutomation #RevenueOperations #ImpactProspectIntelligence

The best “AI SDR” ideas aren't about replacing SDRs ‼️ They're about giving great reps better systems. Here are 5 takeaways from Clay's livestream yesterday on the AI-native SDR:

1. Start the day from signals, not a task list.
Johnny DeFazio from Notion talked about reps beginning in an internal app that surfaces account-level signals: product usage, engagement, warmth, and activity. That becomes the source of truth for what to action.

2. Build your own signal layer if you don’t have PLG data.
Nicole McKelvey from Decagon shared how her team hunts for signals like AI initiatives, leadership changes, competitor mentions, website visitors, new hires, champions, and warm paths. The goal is to give reps a real reason to reach out.

3. Replace hundreds of sequences with one smart shell.
Rob Cook from Clay described moving from maintaining endless persona/use-case sequences to one shell sequence where AI stacks signals, selects proof points, surfaces pain, and personalizes the message. Humans still review, but the system does the heavy lifting.

4. Teach the workflow manually before automating it.
Rob also said Clay has reps do the job manually before leaning on automation. That one stuck with me. If you can’t do the job well yourself, you probably can’t prompt or automate it well either.

5. Fix data before obsessing over messaging.
Nicole McKelvey put it well: garbage in, garbage out. Better targeting and cleaner data make every downstream workflow better.

The big takeaway: The AI-native SDR isn’t a bot.

It’s a rep with better context, better signal prioritization, better prep, and tighter feedback loops with GTM engineering and ops.

Thank you Davide Grieco for hosting a great session 🔥

#GTMEngineering #SalesDevelopment #AI #OutboundSales

Most salespeople are terrified of AI. I’m not.

AI is not killing great salespeople.

It’s exposing transactional ones.

And after 25+ years carrying a quota at the highest levels for AT&T, Verizon, T-Mobile, and Microsoft I believe most people are misunderstanding what’s actually happening right now.

For years, average sellers survived because information itself created leverage.

Customers needed us to:
• Explain products
• Gather information
• Compare vendors
• Translate complexity
• Summarize capabilities
• Coordinate resources

AI is rapidly erasing that advantage.

And honestly?

Good.

Because the best salespeople were never valuable because they had information.

They were valuable because they understood PEOPLE.

According to McKinsey, generative AI could automate up to 60–70% of the activities employees spend time doing today.

Gartner predicts AI agents will soon handle a massive percentage of routine B2B sales interactions.

And Salesforce research shows most buyers now prefer self-service research before ever talking to a salesperson.

That reality terrifies many people in sales.

It doesn’t terrify me at all.

Because once information becomes commoditized…

Trust becomes the differentiator.

AI can summarize a meeting.

But it cannot sit across from an exhausted executive wondering whether this decision could impact their career.

AI can write an email.

But it cannot genuinely understand pressure, politics, fear, burnout, uncertainty, ego, or ambition inside an organization.

AI can automate outreach.

But it cannot earn trust over years of consistency.

That is still profoundly human work.

And ironically, AI is forcing sales back toward what it was always supposed to be:

Human.

The people who are going to dominate this next era are the ones who can:
• Build trust at scale
• Create emotional safety
• Navigate ambiguity
• Understand organizational politics
• Stay calm under pressure
• Connect dots others miss
• Build ecosystems of relationships that survive change
• Make customers feel seen and understood

That’s the future.

I use AI every single day.

Religiously.

It helps me:
• Research organizations in minutes instead of hours
• Understand executive priorities
• Personalize messaging at scale
• Frame strategic meeting hypotheses
• Identify whitespace opportunities
• Analyze negotiation dynamics
• Build better outreach faster

What once took teams days now happens in minutes.

Technology amplifies the person using it.

If the seller lacks empathy, curiosity, discipline, strategic thinking, emotional intelligence, or authentic care for people…

AI simply scales mediocrity faster.

Do you think AI will commoditize salespeople or force the profession to evolve into something far more valuable?

For my entire playbook, check out "Moneyball Sales"
📘 Paperback: https://lnkd.in/gHunVM8R
📱 Kindle: https://lnkd.in/g-3N52Hu
🎧 Audible: https://lnkd.in/gdY6nHkw

All proceeds go to The Michael J. Fox Foundation for Parkinson's Research

Post 224 - Its been a while! In a good way life has been too busy in the real world and in the work world to post on LinkedIn. That said, its a Wednesday so lets see if I can get this rolling again.

AI is a great tool to be able to generate sales copy that is better than the mass emails I get. That said, AI is best utilized as a tool, not to do your job. You still need to be competent. Classic sales outreach strategy says to add personal details. This person went for an easy detail that AI can pick up.

That said, from the structure of the email they went from personal detail to canned message about their solution. You need to commit to personalization, you can't pay lip service to it. Another post on lip service on Friday.