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Last week, I was at a meetup with some of the sharpest SDR leaders in NYC
Everyone was buzzing about AI. Every leader had a tool. Every team had a plan.
Then someone asked a curveball of a question:
“How do we use AI to help SDRs grow into AEs?”
You could feel the pause. Not because people weren’t using AI — but because almost no one was thinking about it that way.
That question stuck with me.
Later that evening, I couldn’t let it go.
So I started digging. Connecting dots. Testing ideas.
Into frontline AI coaching strategies.
Into new research from Winning by Design.
Into how the top go-to-market teams are using AI not just to replace reps but to develop them.
And the answer?
It’s not that we don’t have the tools. We do.
It’s that we’re not using them to teach the skills that matter when you’re no longer setting meetings but closing them.
So, What Makes a Great AE(Account Executive)?
Most SDRs get promoted because they booked a lot of meetings.
But then they struggle.
Because closing is a different game.
You go from:
Talking 70 percent → Listening 70 percent
Scheduling meetings → Diagnosing pain
Following scripts → Navigating uncertainty
Great AEs:
Think on their feet in the moment
Know how to trade and negotiate
Can hold a room with senior stakeholders
Ask smarter questions that shift conversations
These are coachable skills.
And AI can help reps build them before they ever make the jump.
So How Do You Actually Do It?
Here’s a practical approach based on the WbD Report on AI Coaching and what we’ve tested at Blue:
1. Run a 30-Day Impact Sprint
Pick one AE-level skill: e.g., handling price objections or asking critical event questions
Deliver 1 training session (live or async)
Use an AI coach to simulate 10+ reps of that scenario
Track practice, progression, and give feedback weekly
Review call recordings and transcripts for improvement
WbD found that a single coaching sprint improved question-based selling by 3X and increased ARR per rep by 16%.
2. Use AI Roleplays for “Low At-Bat” Skills
Reps rarely get real-world exposure to deal negotiation or exec reviews
Use AI to create high-stakes roleplay environments they can practice daily
Tools like Blue or Second Nature can simulate lifelike deal conversations and give real-time feedback
3. Coach Before, During, After
Before: Generate prep questions and dry runs based on CRM
During: Use light nudges (e.g., reminders on blocker questions)
After: Analyze recordings for missed signals, filler words, or missed CTAs
Bonus: You don’t need to promote SDRs to train them like AEs.
Train them like AEs now.
The best will rise faster.
The rest will still get better at discovery.
One Last Thought
If you're still treating coaching like a weekly “check-in” — you're behind.
Coaching in 2025 is on-demand, scenario-based, and driven by data.
And it’s not just about helping SDRs hit quota. It’s about helping them level up.
We’ve got the tools.
Now let’s use them before your best reps leave to close elsewhere.
Want the full Winning by Design report?
Download it here and send it to your enablement team.
Let’s make AI coaching the norm and not the perk.
That’s it for this week. See you next!
When you're ready, here’s how we can help you grow:
1. Join the SDR Leader Launchpad (Starts August 2025)
India’s first upskilling program built just for SDR Leaders — not recycled AE tactics.
Designed in collaboration with Sam Griffard, one of the Top 25 SDR Leaders globally (2023 & 2024).
Sam brings:
Two formal degrees in sales
14+ years across SDR, AE, Enablement, and Consulting
Frameworks backed by psychology, data, and real-world results
Together, we’ve built the program we wish existed when we were coming up — focused on coaching, culture, and creating the next generation of SDR legends.
Only 2 cohorts this year — first kicks off in June.
2. Hire SDRs from Us
We’re India’s #1 choice for SDR hiring — with recent hires placed at:
Chargebee • Birdeye • Zluri • Whatfix • Salesforce • Zoom • Rippling • Quizizz • Alaan • LambdaTest • VWO • Netradyne • Epicor • Sogolytics • ConvertCart
Looking to scale your team with job-ready SDRs?
Try our hiring engine: GetMeAnSDR.com
3. Try Blue — Your AI Sales Coach
Get instant feedback on your cold emails and cold calls.
Built for reps who want to improve without waiting for a manager’s calendar.
Sign up and get 25 free credits: getblue.ai
Or just browse our free content and upcoming courses:
👉 learn.schoolofsdr.com