06: Outbound Sales = Signal × Message × Momentum (here’s the system)

👋 Hey, welcome back to Pipeline Pursuits - the weekly dispatch for founders, marketers, and operators building GTM systems that don’t break under pressure. If you're piecing together outbound, content, and ops without a clear strategy, this is your cheat code.

Each issue, I share one system, teardown, or workflow designed to help you

• Start better conversations

• Capture more intent

• Build a pipeline that compounds over time

📋 In the next 2–3 minutes, you’ll get:

• A dead-simple outbound sales framework that works

• The stack I use (and I’d use again if I had to start from scratch

• The real metrics that matter

• Playbooks, resource drops ❤️‍🔥 

You’ve probably rewritten the same cold email 10 different ways.

Tried every variation of “quick question.”
Rejigged the CTA.
Slid the signal up or down the message like it’s Jenga.

Still nothing.

The truth is, sometimes, it’s not your writing. It’s not even your offer. You’re sending without a signal. Without structure. Without any rhythm that respects how real people, not job titles, decide what’s worth their time.

Here’s what I use: Signal × Message × Momentum

This is the foundation of outbound sales that doesn’t make your prospects roll their eyes. I’ll break down each part, not just so you can copy-paste a framework, but so you can actually think through where your own outbound is breaking down. Strategy + execution, together. Let’s go.

🔍 “Why Now” - Signals

Signals are my “why now.” It’s the difference between me showing up like I’ve been paying attention, or if I blasted out a generic pitch.

Story time:
Vanta’s sales team uses Clay to surface signal-rich accounts. But they’re not just pulling a list of companies that raised funding and calling it a day.

They’re tracking:

• Job boards for CISO and security role hires

• RSS feeds for funding and compliance news

• Website changes like SOC 2 badges or updated security pages

• Indicators like tech stack tools, competitor mentions, and security-related job posts

The moment a rep claims an account in Salesforce, Clay auto-researches everything and flows it in like this:

That kind of signal-led outbound lets you speak to what your buyer is likely feeling, not just doing. And when you lead with that level of context, you’re already miles ahead of the generic noise.

So when I build outbound, I look for signals like:

• A fresh funding round

• A new role is posted in a critical team

• A website update tied to a known challenge (compliance, hiring, product)

• Tech stack shifts

• A pain-point post from a decision-maker

Signals let me stop guessing. They help me show up with context, timing, and a reason.

Signals Swipe File
If you're ever stuck on what kind of signal to look for, this resource by Common Room breaks down dozens of intent-driven triggers you can use to personalize outreach without starting from scratch.

🧠 Peep the list here. Not sponsored, just something I use in my own outbound.

✍️ “Why this matters?” - Message

This is where most cold email strategies die.

If signal is your 'why now', message is your 'why this matters'. It’s what turns a data point into a real moment of connection.

Let’s go back to Vanta.

Signals helped them identify who to talk to.
But it was the message that made someone listen.

And because I can’t unsee Outbound through the lens of Sherlock now (my partner made me watch it and now I’m a fully converted fan 😎 ), here’s how it lands -

Imagine Sherlock Holmes crafting your email.

He catches the clues no one else sees.

A job board listing here.
A new SOC 2 badge there.
A CEO's “we’re scaling fast” post on LinkedIn. That’s your signal.

But then Watson reads it. He leans back, squints at the wall of clues, and goes, “Sherlock, you genius. But you do realise people have emotions, right? If you send that, they’ll either ghost you or wonder if it was written by ChatGPT on zero sleep.”

So Watson trims it down. Adds warmth. Poses a clear, human question.

Boom. You’ve got messaging that hits both the brain and the gut.

3 golden rules.

1. Lead with the signal. Show them this email is just for them

2. Keep it short. Nobody’s got time for a dissertation

3. Ask something real. Make the reply easy and obvious

And if you’ve never watched Sherlock, that’s totally fine.

The point is - good outbound doesn’t just show you noticed something. It makes the other person feel like you get it. That’s what opens up the reply.

🎁 If you're trying to pair strong signals with equally sharp copy, this one's worth bookmarking. SDRx put together a ChatGPT prompt pack that helps you visualize and write message copy based on context.

📎 Grab it here

⟳ Momentum

Momentum is what turns cold outreach into actual pipeline generation.

You don’t need to nag. You need to layer context.

• Email 1: Signal

• Email 2: Follow-up with adding more context // highlight the problem

• Email 3: Light nudge or LinkedIn ping

• Email 4: (Optional) Part ways or value-forward share

Keep it a 10-14-day cadence to avoid overwhelming the prospect.

🥰 Tip: If your follow-ups feel flat, drop a quick async video in step two. Show your face, mention the signal, and keep it light.

That’s where Wistia shines. Their platform makes it easy to record and share 60-second videos that feel personal, not polished. They pulled insights from 2.7M hours of content and turned it into a report.

I partnered with Wistia to bring this to Pipeline Pursuits because it’s genuinely useful. Especially if you’re trying to use video to move pipeline, not just fill a content calendar.

Wistia analyzed millions of videos so you don’t have to

Wistia, a leading video marketing platform for businesses, just released their fifth annual State of Video Report! The report, based on insights from over 14 million videos, and 100,000 businesses, brings you the latest video tips, trends, and insights. Download a copy to…

• See how your videos perform against industry benchmarks

• Learn which kinds of videos get the most engagement so you can make more of them

• Find out how to scale your video strategy for less $$ with AI

Plus, it’s actually fun to read. How many reports can you say that about?

Get your free copy

🛠 Tech stack I use

Here’s what I run when I have to build a clean outbound system for my clients -

• Clay - outbound sales ecosystem

• Instantly - email sending provider. Connect all accounts

• Loom - async videos that feel personal

• Notion/Google Sheets - to track replies + patterns

• Zapier - glue it all together

Simple. Effective. Easy to manage solo.

Your list-building tools can differ according to your ICP.
Example - for Robin AI, we used Preqin instead of Apollo or LinkedIn. It’s a good database of private equity companies.

If you're sorting through tools or just want a second opinion on your stack, reply to this email. Happy to jam and share ideas.

Now, track the following…

Track the following -

• Open Rate - above 50%

• CTRs - between 3% to 5%

• Reply rate - 3% is good

• Positive replies - 30% of reply rate

• Objections - tagged by theme

• Time to reply - under 6 hours

Outbound sales gets easier the more you treat it like a feedback loop. You’re not measuring to punish you’re measuring to tune.

That said, don’t obsess. And please don’t hound your SDRs if things dip for a week. Unless your CMO made a LinkedIn post about "accountability culture" this morning. 😆 In that case, maybe just forward them this instead.

If something’s off, it usually means the system needs tuning.

I’ll break down exactly how I run outbound audits (and drop a template) every 15 days.

Read about it in the next issue. Subscribe if you’re not on the list.

✉️ Until next time

If this issue gave you a helpful nudge, do me a quick favor. Reply to this email or click one of the links above. It helps keep the deliverability gods happy and ensures this newsletter keeps landing in your inbox (not the Promotions tab).

Always down to jam on systems, workflows, and what’s working in the field, lmk.

See you next week ❤️‍🔥
Siya