Most startups are leaving money on the table. Every month, leads sign up for your product, register for your webinar, or show intent—and you're sending them the same generic welcome email everyone else sends.
Jacob Bowman, Founder and CEO of OutboundLeads, recently presented a demo that flips this approach on its head. His demo showed how to automatically research every inbound lead and craft hyper-personalized messages that prove you actually understand who they are and why they signed up.
The Problem: Generic Messages Don't Convert
Jacob opened with a simple question to the room: "How many of you each and every single month are getting some type of inbound lead or sign-up to a webinar or any other type of trigger that you're not capitalizing on?"
The answer? Most founders are sitting on untapped opportunity. When someone shows interest in your product, they're giving you permission to reach out—but most companies waste that moment with cookie-cutter automation that treats every lead the same.
The Solution: Automated Deep Research at Scale
Jacob walked through a live workflow that combines Clay and Twain to transform how you respond to sign-ups. Here's how it works:
Step 1: Capture and Enrich Sign-Up Data
When someone signs up, their information flows into Clay through a webhook or API. The system immediately:
- Validates their first and last name
- Looks up their information in HubSpot
- Determines if they're using a professional or personal email
- Runs a waterfall enrichment to find their LinkedIn URL
This foundation gives you the basic data you need to understand who's showing interest in your product.
Step 2: Twain's Deep Research Engine
This is where the magic happens. Twain's newly launched sequence enrichment feature (which had been live for just 24 hours at the time of the presentation) automatically researches each sign-up. Jacob demonstrated using Nick from HeyReach as an example.
What makes Twain different? It doesn't just scrape LinkedIn. The platform:
- Pulls insights from multiple sources including YouTube videos, podcasts, and public content
- Extracts transcripts and understands context
- Provides citations with direct links to source material
- Delivers 2-7 unique insights per prospect in seconds
As Jacob noted, "I don't have to sit there and do manual research. I don't have to sit there and look on Google where this person is and what they're talking about. Twain's doing everything for me, and it's within the matter of seconds."
Step 3: AI-Generated Personalized Sequences
Twain doesn't just research—it writes. The platform automatically generates personalized message sequences based on its findings. Jacob shared an example message sent to Nick that demonstrated the level of personalization possible:
The message referenced specific details about HeyReach's product setup, their user-driven roadmap approach, and even made predictions about their tech stack—all verified as accurate by Nick in the room. The message ended with a relevant video showing exactly how Twain's deep research feature works.
Jacob posed the question: "I'm sure everyone here signs up for all sorts of different softwares all the time. You're probably getting extremely generic messages that are very irrelevant to you. So just out of curiosity, if someone signed up for Twain and received this message, how intrigued would you be?"
The room full of smiles said it all.
Real Results: Booking Meetings with the NBA and Apple
Jacob shared two standout results from using this approach:
NBA During Playoff Season: OutboundLeads sent a 100% Twain-generated email on behalf of a client on June 4, 2025—right in the middle of the NBA's busiest time of year. They booked a meeting and put the NBA in their client's pipeline.
Apple: An outbound message to someone at Apple was so well-researched and personalized that it got forwarded to the actual decision-maker, who replied and booked a meeting. That client is now in active negotiations with Apple.
The Apple example is particularly telling. The initial message was so relevant that an internal forward happened—the ultimate sign that your outreach cut through the noise.
Pushing Insights Back to HubSpot
The workflow doesn't end with the message. All the research and insights Twain generates automatically sync back to HubSpot. This means when a demo gets booked or a lead gets passed to sales, your team shows up to the call with full context—completely automated.
Jacob emphasized the impact: "Your sales reps and yourself can actually show up with context on the call, and all of this has been completely automated for you."
Why This Approach Works
Before tools like Twain, agencies like OutboundLeads had to cobble together workflows using Claude, ChatGPT, and Perplexity. Jacob's team sends over 500,000 emails monthly for 15 clients, and quality control was nearly impossible to scale.
The key insight: When someone signs up for your product, they should immediately see what your product can do. Don't just tell them about features—show them you understand their world, their pain points, and why they're exploring your solution in the first place.
The Bottom Line
Every inbound lead is an opportunity to make a real connection. The difference between a generic drip campaign and a personalized sequence built on actual research can mean the difference between a churned trial user and a customer who sees immediate value.
With the right automation stack, you can deliver that white-glove experience at scale—without adding headcount or sacrificing quality.
AI Disclaimer: AI helped us summarize the key points from these videos, and our editorial team reviewed everything to make sure it's clear and correct.
