Everyone is talking about AI in sales right now.

So am I.

I’m a big believer in it. We’re building an AI GTM company at Pitstop, and I use AI every day in my own work.

But today I posted a job advert for a Revenue Associate to support me in founder-led sales.

That is not a contradiction.

It is because I think AI will augment salespeople far more than it will eliminate the need for good ones.

AI is already incredibly useful. It can help with research, preparation, summarising calls, drafting follow-up, reducing admin, and generally making sales execution faster and cleaner.

That matters.

But there is still a big difference between supporting execution and owning judgment.

Good sales support is not just about getting tasks done.

It is knowing what matters in a live deal.
It is spotting weak signals early.
It is helping decide where founder time should actually go.
It is maintaining momentum across real conversations, not just generating more activity.

That is why, even as someone building in AI, I wanted to open a role for a person to work alongside me.

I doubt I’m the only one who sees it this way. Even frontier AI companies like Anthropic are actively hiring account executives, sales development, customer success, and sales leadership roles.

That tells you something.

The future of sales is not AI or people. It is AI making good salespeople better.

And it is probably increasing the value of the people with the best judgment, discipline, and commercial instinct.

AI can raise productivity.

I still think great people are the edge.

Curious whether others are seeing the same thing.

Richie Choudhary Thomas Copeman Steve Davies

🤖 i'm using AI every single day as a head of sales 🤖

not to replace me or my judgment

but to make it sharper ✏️

and i'm trying to figure out how to learn AI faster and use AI better


here are 3 ways i used AI last week:

1️⃣ coaching reps

before every 1:1, i ask AI to pull the key moments from my rep's recent calls

AI surfaces the patterns

i show up to the 1:1 with specific drills to run with each rep based on what they specifically need to work on

AI is making me a more confident, effective, and well-prepared manager




2️⃣ new hire onboarding programs

i built comprehensive 10-day onboarding programs with AI as my co-architect to help reduce ramp time for new SDRs and AEs that join our team

and not just "hey make me a training plan"

i fed it learning theory frameworks + our Notion instance (with our ICP, our sales motion, our product) and i asked it to build a program that actually transfers skills, not just knowledge

i'll report back with feedback from our upcoming new team members



3️⃣ Granola takes better notes than me then drafts emails to send to prospects

normally, i hate AI email drafts and i end up spending more time editing the AI draft than i would just drafting the email from scratch myself.........

not anymore

fast and valuable follow-up emails sent FAST







the common thread????

AI isn't doing my job

it's making sure i'm doing my job at the highest level possible

******************************************************

i'm starting a new series on this

AI + the modern sales leader

where i share exactly how i'm using AI to build, coach, and scale in real time (because i want to consume more content like this so figured you might too!)

selfishly, trying to get to 10K followers too. think talking about AI can get me there? no idea, but we'll see.

🤖 follow along 🤖

AI in sales is one of those things where once you use it, you can't really go back.

And I am not talking about it replacing humans.

I am talking about the efficiency gains.. Not just getting faster, but also producing better outputs.

I love to frame using AI as a way to "make my outside the box ideas & thinking come to life" in a more meaningful way.. With AI being there to question me & challenge how I am thinking about certain scenarios.

It's fun stuff.

One of my favorite recent use cases is call prep and creating exec summaries for clients.

Being able to stitch together unique data sources into one cohesive story in minutes is a huge unlock.

More to come.. Anthony Intelligence (AI)

Spent the last few weeks thinking about this because I keep seeing posts about AI killing sales and clientfacing roles.

Quick background, Senior AM at a high-ticket consulting firm. 3 years in the role. Work with clients from earlystage to 2 mil + businesses.

Here's my honest take after using AI heavily in my workflow :)

AI is great at tasks. It is terrible at humans.

And account management, at its core, is a human job. Specifically

Clients don't pay for information, they pay for accountability. AI can generate a strategy. It cannot call you out when you're avoiding executing it and That's what I do.

Reading a client's real state ,not what they say, but what they mean . is a skill built over hundreds of conversations. No model has sat through what I've sat through.

When things go sideways (and they always do), clients don't open ChatGPT. They call their AM. Ownership and trust are human things.

My actual workflow >> AI handles prep, research, templates, summaries. I handle judgment, relationships, escalations, and the hard conversations.

Net result: I have more bandwidth for what actually moves the needle.

The role isn't dying. It's being filtered. Average AMs who coast on coordination will struggle. AMs who bring real judgment and use AI as a force multiplier? More valuable than ever.

Anyone else in client success finding this to be true???

I used to waste hours writing cold messages, rewriting follow-ups, or thinking of ways to re-engage dead leads.

Now?
I use AI — but not in the generic "ask ChatGPT for help" kind of way.
I built a Lead Gen Prompt Library with 15+ proven prompts that are actually designed for sales professionals.

What it does:
✅ Generates high-converting cold emails
✅ Writes personalized follow-ups in seconds
✅ Handles objections with pre-trained responses
✅ Scores leads based on input data
✅ Helps with reactivating past contacts

Basically, it took all the repetitive stuff off my plate — and gave me better results.

🔗 I made the prompt library free to download here → <https://bizhack.rs/free-prompt-library-for-lead-generation-professionals/> fill it out and get instant access, no hidden stuff....

Perfect if you:

Work in sales, consulting, or lead gen

Want to get better at AI without spending hours learning prompt engineering

Are tired of generic results and want real, useful outputs

Hope it helps someone! Happy to answer any questions or share how I use it inside my workflow.

I've been using AI tools more seriously over the last few quarters.

And something unexpected is happening.

The more I use them, the more I notice what they can't do.

They can research a prospect in seconds. Summarise a call. Draft a follow-up. Build a pipeline report.

Genuinely impressive.

But here's what I keep coming back to:

The moment a conversation gets uncomfortable — a budget freeze, a political landmine, a relationship that's gone cold — the AI does not know what to do next.

That stuff lives in the grey zone.

And the grey zone is where enterprise deals are actually won or lost.

I'm still figuring out exactly how AI changes the job. I don't think anyone has fully worked that out yet.

But my instinct after 21 years?

The fundamentals don't get replaced. They get amplified.
Trust. Curiosity. Reading a room. Knowing when to push and when to go quiet.

If anything, AI might be the thing that finally makes us take those skills seriously again.

Curious what others are seeing — especially those of you deeper into AI-assisted selling. What's surprised you most?

#Sales #AI #EnterpriseSales #B2BSales

I'm Head of Sales at an 18-person startup.

And I'm going 100% AI native.

I do the normal stuff:
→ Run demos, close deals, follow up on proposals
→ Build playbooks and outreach strategy
→ Sit between product and customers - nothing gets lost in translation

But there's an AI stack running behind me that does the rest.

1. Allo (AI Phone System) (our own AI receptionist + phone system)
→ Handles every inbound call when I'm busy or asleep
→ Qualifies leads, answers product questions, books demos on my calendar
→ Last week a prospect called at 11pm. AI picked up, captured their team size, CRM setup, and which phone system they were migrating from. Booked a demo for Wednesday morning. I woke up to a fully logged summary in Attio

2. Claap (call intelligence)
→ Records and analyzes every sales call
→ Sends me a weekly report: why we won, why we lost, biggest objections
→ Monday morning before I plan my week. Like having a rev ops analyst I never hired

3. Claude (research, analysis and deal intelligence)
→ Connected to Claap, I can ask anything about any deal at any time without opening my CRM
→ Claap records the call. Claude tells me what to do next, and how to prep for the one after.
→ Our investors sent a list of 400 portfolio companies to prospect into. Claude broke them all down by fit and prioritized by ICP match. Would have taken me days. Took about 20 minutes

4. Wispr Flow (voice to text)
→ I think out loud. It captures everything. Nothing lives in my head anymore.
→ Crazy high accuracy and is saving me so much time.

5. Shortwave (AI email)
→ With custom prompts and AI memories, I can draft an email in seconds
→ Ironic because I sell a phone product and genuinely prefer calling people

That's 5 tools running behind one person.

I'm not technical.
I can't write code.
But I use AI to scale revenue every single day.

What am I missing!

A year ago, account planning took me 3 days. Slide decks meant starting from scratch. And I was drowning in post-call admin.

Here's what my workflow looks like now with #ai — Anthropic specifically:

1. *Account plans in minutes* I feed Claude the company's latest earnings call, LinkedIn intel, and recent news. Claude already knows what General Assembly does best and has learned when we win. It outputs a full account plan — pain points, buying triggers, stakeholder priorities, and a recommended approach. What used to take 3 days now takes 30 minutes.

2. *Slide decks built from our own winning proposals* I've built a repository of our best proposals and pitch decks. Now I prompt Claude to pull the most relevant slides, adapt the messaging for the new prospect, and structure a first draft. I start from 70% done, not zero.

3. *Never miss a thing from a call* Granola has changed my life. Truly. It captures everything and gives me structured notes and action items the moment the call ends. especially because I am usually back to back calls and drowning in lists of to-do's — ultimate clutch when I can't record via Outreach.

4. *Stakeholder maps that actually drive strategy* Before any major deal, I use AI to build a full stakeholder map with a recommended engagement approach for each person. I can see the landscape of an account before I ever step into a call... pretty Natalie (Corporate Natalie) to meet a new stakeholder and say: omg it's like i'm meeting my favorite influencer since I've already researched everything about you 😭

For everything else, there's Krysten Conner and Nate Nasralla. Their tips and thought leadership power 80% of my deal strategy... and I've been a top 3 enterprise seller at GA for the last 4 years 🙂

#ai is making us faster — but Krysten and Nate keep us human, and that's the real reason we win. Now onto, #agents . Excited to automate SDR work in 2026+

#EnterpriseSales #AIinSales #SalesProductivity #GeneralAssembly #Claude #Anthropic

Ps. if you're obsessed with fascia or MotoGP Sports Entertainment Group... let me know 😂⬇️

Here’s every way I currently use AI in sales:

- Find “lookalike” accounts for deals we’ve recently won so I can prospect best-fit accounts (thank you Kyle Asay)

- Find the best exec-level problems to hypothesize in my cold outreach and discovery (thank you Jen Allen-Knuth)

- Draft my cold emails within extremely specific guidance and a messaging matrix - I always edit before sending (thank you Jason Bay)

- Consolidate prior convos into high-level problem statements to recap at top of calls (thank you Nick Cegelski)

- Build one-page business cases (thank you Nate Nasralla)

That’s it. There is a lot of manual work involved still. AI produces almost nothing that is customer-ready on the first go.

I’m not anti-AI

But I am anti-always-talking-about-ai-every-second-of-every-day

I use AI in every part of my sales process.

Tried almost everything out there, narrowed it down to three tools: Claude Code, Claude Cowork, and Lindy. If I'm building something from scratch, Supabase and Vercel too.

Here's exactly how I use them:

1/ Account + call prep

→ Account maps, strategic business objectives, exec behavior, investor behavior, team dynamics, recent intel. I have a full picture before every single call.

2/ During + after the call

→ Call recording pushes deal info to CRM. Champion follow-up and nudge reminders. Action items, collateral, case studies, business case drafts → AI gives me the v1, then I use it as a thought partner and collator for the final version.

3/ Deal management

→ CRM updates as deals move through stages. At-risk deal flags. Forecasting based on actual signals (emails, texts, call transcripts, usage).

4/ Reporting + dashboards

→ Pipeline visibility. Summon through Slack, text → instant reports, dashboards, insights.

5/ Coaching

→ After every single call I get coaching sent to my phone. Voice note or text. End of the week, a synthesized coaching summary. Patterns, strengths, where to sharpen, what best practice am I lacking, goals and accountability.

6/ Prospect intelligence

→ ICP refinement. What pain points resonate, what messaging lands, deal blockers, competitive intel, etc. After enough calls, AI starts showing me patterns I wouldn't catch on my own. Which personas convert fastest, what objections show up at which stage, where deals actually die.

I think most sales leaders are overwhelmed right now with when and how to use AI. There's too much noise. This is what's actually working for me.

What am I missing - what have GTM folks found most valuable?