Generating Your First Customer Conversations as a Founder: A Guide to Doing Outbound Right
I’m a big believer in delegation and automation - but only when it comes to things that don’t directly impact company priorities. Stuff below the line. Admin. Legal. Ops. The kind of work you can offload so you can stay focused on what actually moves the needle - and on the things only you can do.
But speaking to customers? Listening to them? Driving pipeline?
That’s not below the line. That’s your job.
Especially at the start, when not a lot is figured out: your messaging, your ICP, even the actual shape of the product. Founder-led sales isn’t just about getting meetings. It’s how you find your hypotheses, test them, and refine what you’re building.
The myth of scalable outbound
High volume, automated outbound can work - but only after you’ve figured out what works. When you’ve got product-market fit. When your ICP is clear. When you know the messaging converts. Only then does automation make sense - because you’re scaling a process you’ve already proven drives ROI.
But automation won’t find that process for you. Spray-and-pray outbound doesn’t get you insight - it gets you nowhere.
In the early days, what you actually need is clarity. And the best way to get clarity is through specificity.
Focus sharpens everything
When I’m doing outbound, I don’t start by writing a message. I start by asking: who, specifically, do I want to speak to - and why?
When I’ve done that properly, the message usually writes itself. I know what I want to say, why this person matters, and what I’m hoping to learn. I go into it with a hypothesis, and every reply helps me sharpen that.
Sometimes that means spending 30-minutes crafting a single message. And honestly, that’s what it takes. Because I’m not looking to get 50 meetings from scaling at a 0.5% conversion. I’m trying to get that one conversation that helps me move the company forward.
If I set my sights on someone I believe is worth talking to - I find a way to get the meeting. Whether it’s through the perfect message, a warm intro, or just being a bit relentless.
Early Autoplay: how I got my first calls
When I first had the idea for Autoplay, there were three products that inspired it - because I’d used them, and experienced the exact problem I was trying to solve.
They were big companies. Public SaaS companies. But I knew who I needed to speak to. I spent real time writing each message. I told the story of why I was reaching out, the struggles I had as a user, and what I was building.
Every single one of them replied and met with me.
I don’t say that to flex. I say it because the messages were honest. I actually cared about the conversation, and I wrote something that made it obvious.
When I write a cold message, I ask myself:
“Would it be rude for them not to reply?”
That’s my bar. If the message doesn’t meet it, I don’t send it yet.
Why most outbound gets ignored
Most outbound messages feel like ads. We scroll past them like we drive past billboards. They’re not for us, they're for everyone (who might look a little like us at best).
But when a message is clearly for me, and it’s obvious that a real human spent time writing it on the other side - I actually pause, and show my attention back.
I’ve seen this firsthand. Back when I was selling Encord, I had the lowest outbound activity on the team. But I consistently had the highest-value pipeline. I reached out with intent and purpose. Over 50% of my messages replied, 80% of those conversations turned into opportunities, and more than 50% of those closed.
Same process I use now.
The structure I always follow
Whether it’s a customer I want to learn from or a buyer I want to pitch, my messages all follow the same structure:
Story – Why I’m reaching out to you, specifically, and why now
Signal – Something I’ve learned or observed that signals a pain point or fit
Solution – What we’re building and why it’s relevant
CTA – A clear, honest reason to meet
Here’s an example of a real message I sent in the early days of Autoplay (minus the name and company):
Hi John Doe,
Hope you don’t mind the cold note - I actually worked with the XYZ team at my first company, Celebrating.Live, to plan your virtual holiday party during the pandemic. Your team was awesome to work with, so I imagine there’s a lot to look forward to now that you’ve joined post-acquisition.
I just founded a new (and completely different) company, inspired partly by my experience as an XYZ customer back then. I remember your sales and CS teams were real power users of the platform, but translating their knowledge into our own workflows wasn’t easy. If I’m being completely honest – I struggled early on to learn the best way to use the product…
I’m now building Autoplay to guide users in real-time based on their specific intent or goal, so they don’t have to rely on hand-holding or help centres to figure things out.
Since your team is owning the implementation of AI to improve the user experience, I’d love to hear what’s been working (or not), and share a bit about what we’re building. We’re still early, refining our MVP – so feedback at this stage really shapes the direction of where we’re going..
Best,
Sam
Why did this message work?
Because it’s not trying to sell. It’s trying to connect. It’s a real story. It has context, meaning, and timing. It invites a conversation, not a pitch.
And that’s the whole point of founder-led sales. Not to scale - but to learn. To get sharper. To build something that works, one honest conversation at a time.
Where Tools Do Help
Most tools that promise to “automate” outbound just push you toward the wrong game: more volume, less learning. But there’s another category that can actually help - the ones that strip out the admin so you can focus on the part that matters.
Lately, I’ve been using a tool called Sendegg. It doesn’t try to replace the hard part (writing a message worth replying to). Instead, it quietly clears the busywork - the copy-paste from LinkedIn to CRM, the endless updating of stages, the forgotten notes.
It’s not magic. But when those little frictions disappear, I get to spend my energy on the conversations that count. And that’s the only part of outbound that really moves the needle.
My Sendegg workflow (step-by-step)
Pick a lane
Define the micro-ICP and one hypothesis (who/why/what I want to learn).LinkedIn search
Open LinkedIn quick search for my ICPOne-click capture
Save search results to Sendegg as a listAI narrow down
AI will narrow down further based on the ICP criteria I gave it (e.g. "currently a PM at a B2B saas AI startup")Autocomplete the context
Sendegg enriches the record (work email, company info, useful signals) so I’m not hunting around.Slot the stage
Drop them into the right stage (e.g., “Targeted → Drafting”). Keep stages truthful.Write the note, not an ad
Draft the 4-part message (Story → Signal → Solution → CTA). Templates only for scaffolding.Send from a campaign or 1:1
If it’s a small batch with the same hypothesis, I use a lightweight campaign. If it’s truly bespoke, I send 1:1.Set the nudge
Create a follow-up in 3–5 days (new info, not “just bumping”). Sendegg tracks who’s due.Let replies move the deal
When someone replies, the contact auto-advances to “Engaged → Discovery.” No manual stage shuffling.Capture the learning
After the call, I add quick notes (pain, language they used, next step). Tag by signal (ICP fit, friction, timing).Advance or archive
Move to “Opportunity,” “Later,” or “No fit.” Dead-honest pipeline beats fantasy pipeline.Rinse with intent
Use Discover to surface the next best matches for the same hypothesis. Repeat with focus.
What Sendegg is doing behind the scenes
LinkedIn → Pipeline, instantly: Captures the profile and creates a contact/deal in the right place without opening another tool.
AI narrow-down: Filters your connections/search results to surface only the ones that match your ICP, so you’re not cluttering the pipeline with noise.
Auto-enrichment: Pulls email + company details so outreach is ready fast.
Stage automation: Replies and sends update stages so the pipeline stays accurate.
Campaigns tied to pipeline: Simple email sequences connect directly to contacts/stages - no CSV juggling.
Templates + variables: Speeds up the repeatable bits while keeping the message human.
Discover view: Surfaces high-fit people so you’re not scrolling endlessly.
Single activity trail: Messages, notes, and status changes live together - you can pick up tomorrow without re-contextualizing.