AiSDR Product Spotlight #38: GPT-5 for Outreach is Here

Ever dreamed of traveling back in time? 

Don’t bother. Just recall the times when generic outreach was considered perfectly fine: 

• A name 
• A title
• A value prop
• Call to action… (maybe?)

Worked like a clock that only works some of the time.  

Yikes. 

Thankfully, this is 2025, and we have generative AI and advanced LLMs. 

Today’s prospects see hundreds of messages a week. Most get ignored. 

The ones that break through are the ones that show they actually know you. They reflect what you’re working on, your challenges, and your priorities, while offering a solution that solves your pains. 

Because when it comes to personalization, context is king. 

And that’s where generative AI changed everything. Instead of writing every message by hand, reps can feed in context and let a model craft outreach for them.

Cut to… we now bring GPT-5 and GPT-5 Thinking into AiSDR.

🧠🎯 GPT-5 personalization is live 

Simply put, you can now use GPT-5 and GPT-5 Thinking to build more context-driven, sharper personas and outreach. 

Early models had their limits. They worked with short prompts, lost context in longer conversations, and left room for error. 

Each newer generation of LLM improved on the last by fixing gaps and expanding capabilities. And that journey now brings us to GPT-5 and GPT-5 Thinking.

What’s changed with GPT-5 models?

Previously, AiSDR’s live AI personalization used OpenAI o3 to scan each lead’s digital fingerprint and surface three product-specific insights. It worked behind the scenes to make messages feel more relevant without extra effort.

GPT-5 and GPT-5 Thinking take that foundation further by pulling in more context and selecting insights with better timing and a tighter connection to your product.

This brings personalization closer to human-level relevance than ever before.

How it works

You can select GPT-5 and GPT-5 Thinking as the generation model while building or editing any AiSDR campaign.

This gives your outreach deeper context and a more natural flow, so messages feel closer to how a human would write them.

Every other part of campaign setup stays the same.

Why it’s cool

Deeper context: GPT-5 can process longer briefs, product docs, and full conversation histories without losing track. This helps every draft reflect the bigger picture.

Sharper personalization: With GPT-5 Thinking, live AI now highlights timely company moves or role changes that matter to your lead, then ties them directly to your product’s value.

GPT-5 in action

Imagine a prospect just stepped into a new leadership role. 

Here’s an email AiSDR sent just recently:

Notice how the outreach ties a recent local event (Milwaukee Art Museum’s app) to the lead’s industry focus (360VR and immersive formats), then naturally connects to the product’s positioning?

That’s GPT-5 Thinking hard at work.

It goes beyond surface-level signals and crafts a message that feels like it was written by someone following the same news as your lead.

The result? 

Outreach that carries more weight and gets a higher chance of a real reply.

🤫 Next week’s sneak peek

The summer may be wrapping up, but there seems to be no shortage of updates 😉 Stay tuned!