We Sent 4,495 AI SDR Emails in 2 Weeks and Got The #1 Response Rate. Here's How (It's Not What You Think)"
"The difference between good and terrible AI outbound isn't the tool — it's whether your AI actually provides value to the recipient."
After less than 30 days with our AI SDR, we became the highest response rate on our AI SDR platform. #1. Here's what actually works — and what doesn't.
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We've all gotten that terrible AI SDR email. You know the one: "Hey [FIRST NAME], I did some research on [COMPANY] and thought you might be interested in [GENERIC PITCH]."
Yeah, that's not what we're talking about here.
In just two weeks, SaaStr's AI SDR sent 4,495 hyper-personalized messages, opened pipeline, booked meetings, and reactivated lapsed accounts — all while outperforming our historical human SDR averages.
But here's the thing: it took a lot more work than just "turning it on."
If you think you're going to flip a switch and watch the magic happen, you're in for disappointment. But if you're willing to put in the effort to train it right, the results can be extraordinary.
The Reality Check: Our Unfair Advantages
Before we dive in, let's be honest about why our results were so strong:
We have a brand. SaaStr has been around since 2012. People know us.
We targeted our existing database. These weren't cold prospects — they were website visitors, past attendees, and folks who had engaged with us before.
We spent two weeks doing basically nothing else (beyond our normal day jobs). 90 minutes in the morning, an hour at night, plus real-time responses throughout the day.
If you don't have a brand and you're planning to blast cold lists, your mileage will vary. A lot.
Top 10 Learnings for Making AI SDRs Actually Work
1. Your AI Has to Add Real Value (Not Just Send Volume)
The difference between good and terrible AI outbound isn't the tool — it's whether your AI actually provides value to the recipient. If your AI is sending "Hey, saw you on our website" messages, you're doing it wrong.
Our AI references specific SaaStr events people attended, congratulates them on new roles it found on LinkedIn, and suggests relevant programs based on their company profile. The bar is: would I have written this email myself?
2. Expect to Spend the Same Time Training AI as You Would a Human
This isn't a "set it and forget it" solution. Plan to spend at least two weeks of intensive training, just like onboarding a new hire. The upside? You can train the AI at 6 AM or 11 PM — it doesn't need traditional work hours.
For the first two months on our website AI, our general chat, we spent 30 minutes every morning auditing conversations, catching errors, and manually writing better responses for the AI to learn from. Now we do it once a week.
3. You Need ALL Your Data (And It's Probably Messier Than You Think)
Your AI needs to be trained on everything: CRM data, marketing automation platforms, website content, past event attendees, sponsorship history — all of it. We trained ours on 20+ million words of SaaStr content.
But here's the reality check: your data probably isn't as clean as you think. We found opportunities that were never logged in Salesforce, missing context from AEs who never used the system properly, and gaps everywhere.
Pro tip: Start with a data cleanup before you even think about AI.
4. Hyper-Segmentation Is Everything
The more you can segment your AI campaigns, the better they'll perform. We ran separate campaigns for:
Lapsed sponsorship accounts
Previous event attendees who haven't returned
Recent website visitors
Cold outbound (this performed worst, as expected)
The website visitor campaign was hit-or-miss. The reactivation campaigns? Those were money.
5. Human-in-the-Loop Isn't Optional — It's Required
The AI alone is not enough. Period. You need humans actively involved in the process, not just reviewing outputs once a week.
When prospects responded to our AI, I had to respond instantly — and at the same quality level as the AI. The expectation is that you're always "on" because the AI created that impression of responsiveness.
6. Don't Expect It to Replace Everything
This is additive to your existing sales and marketing efforts, not a replacement. We still send personal emails, we still do marketing air cover, we still have human SDRs. The AI just lets us touch way more accounts at a personalized level.
Think of it as 3-6 combined touchpoints, not a single magic solution.
7. Go Way Beyond Just Outbound
If your AI is booking meetings for you (and it should be), you better know everything it knows when you get on that call. We developed what we call "The Four C's" for pre-call research:
Chat: What did they discuss with our AI?
Claude/ChatGPT: Full company research and "why should they buy from us?" analysis
CRM: What's our history with them?
Cluely (or similar): Real-time intelligence during the call
Come to every call with a working theory about why they're interested, not a generic discovery process.
8. Create Dynamic, Customized Follow-up Materials
Stop sending generic sales decks. AI can create fully customized proposals and presentations in minutes based on your specific conversation. I use tools like Gamma and Genspark to create tailored booth options, pricing proposals, and company-specific case studies.
The prospects love it. Who wouldn't want a custom deck that actually addresses what you just discussed?
9. It's More Work, Not Less — But Higher Quality Output
Here's the uncomfortable truth: doing AI right is more work than not using AI at all. You get 10x better output, but it requires "S-tier human orchestration" to get top-tier results.
You can't just hand this off to junior ops folks or agencies. It requires someone who knows your business deeply and can provide high-quality training and oversight. Every single day, and maybe, all day long.
10. Audit Everything Daily (At Least Initially)
Spend 30-45 minutes every single day reading a sample of what your AI sent. When you find something wrong, don't just fix it — teach the AI why it was wrong and what to do instead.
After 60 days of daily improvements, you'll have something you're proud of. But you can't skip this step.
The Tools We Use (Since Everyone Asks)
AI SDR Platform: Artisan, Qualified, Amplemarket, etc.
Data Enrichment: Lusha, Seamless, ZoomInfo, Apollo
Presentation Generation: Gamma, Genspark
Call Intelligence: Claude and Perplexity ahead of time, Cluely for real-time research
Training Data: 20+ million words of SaaStr content, 10+ years of CRM data and marketing automation data
What Doesn't Work
Bad AI Email Example: "Hey SaaStr team, how's it going? I did a bit of research and thought you might be familiar with [COMPANY NAME]. We help companies like yours with [GENERIC BENEFIT]."
Good AI Email Example: "Hi [NAME], saw you attended SaaStr London last year and just noticed your move to [NEW COMPANY] — congrats! Given [COMPANY]'s focus on [SPECIFIC AREA], thought you might be interested in our 2025 London program, especially our new VC track..."
See the difference? Specific, relevant, valuable
The Bottom Line
AI SDRs can work incredibly well, but only if you're willing to invest the time to train them properly. This isn't about replacing humans — it's about augmenting what humans can do with hyper-personalization at scale.
The companies that figure this out first will have a massive advantage. The ones that just turn it on and walk away will wonder why they're getting the same terrible response rates they always have.
Pick your platform, commit to the training, and prepare to spend more time on orchestration than you expect. But if you do it right, you'll be sending thousands of emails that sound like you actually wrote them.
What We're Looking to Do Next
We're literally onboarding two more AI sales tools this week. The outbound piece is working, but we want to go deeper across the entire sales cycle.
We're still hunting for a really good AI marketing tool — if you know of one that actually works (not just another content generator), hit us up.
We're also hiring someone specifically to manage our AI operations. A human :) This is becoming a full-time role and frankly, we need someone whose entire job is orchestrating these systems. If you know someone good at both AI and revenue operations, send them our way.
The goal is to have AI touching every part of our sales and marketing funnel by the end of the year, but doing it right — with proper training, human oversight, and real value creation.