🔥 pipeline booster

Four signs your outreach is blind activity

Daily Sales Newsletter

September 01, 2025

 

Welcome - this is your daily dose of sharp, tactical sales advice.

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In today’s issue:

  • Aaron Reeves: Replace messages with qualified targeting

  • Mark Roberge: Handle pitch request by meeting schedule

  • Matthew Putnam: Align sellings feature to prospects needs

  • James Bissell: Video message that actually land prospects

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Replace messages with qualified targeting

Aaron Reeves highlights that outbound isn’t complicated. Most reps fail because they’re operating blindly, not because cold outreach itself is broken. Here’s the breakdown:

1. Input = qualified signal

âť– The majority of reps confuse activity with effectiveness.

❖ Sending emails to the wrong people doesn’t create leads.

âś” Target people who show intent, have active projects, or are recently changing

âś” Build prospect lists around signals: hiring opportunities, regulatory pressures

Example: If a VP of Engineering just recently hired 5 new developers, they are more likely to have new onboarding pains worth addressing.

âť– Once lists are built, use channels to get in front of those ICPs.

2. Iteration beats volume

The best reps aren’t just “doing more.”

They’re adapting based on datas given.

➤ Track email performance: open, click, reply, and meetings booked

➤ Track call performance: conversations held, and meeting outcomes

↳ Calibrate messages after every 30–50 touches.

↳ Treat your pipeline like an ongoing experiment

Example: When follow-ups get no response, replace them with similar messages:

“You mentioned compliance eats 10+ hrs/month. Did you solve that yet?”

3. Visibility unlocks results

The silent outbound killer is when nobody knows what’s effective.

– Marketing runs one playbook

– RevOps tracks pipeline stages

– Sales reps just keep guessing

✔ Without visibility, you’re running blind.

✔ You can’t double down on what works.

Knowing vs. thinking scale pipelines differently.

Handle pitch request by meeting schedule

Mark Roberge explains how to respond when prospects says, “Pitch me.” Don’t go instantly to full product dumps. Book meetings and steer back to discovery instead:

Don’t pouce on baits

When a prospect says “pitch me,” you’re tempted to pitch features.

But you don’t know yet what really matters to your potential clients.

âś” Keep it short when called for:

“Most customers use us for [A], [B], or [C]. Which is most relevant to you?”

âś” Pivot back to questions uncovering their interests

Focus on the meeting

Your job is booking next steps, not running a full sales cycle.

  • Offer time slot availability instead of listing too many

  • Confirm time zones and calendar invites on the spot

  • Get leads to accept invites promptly for better rates

Example:

“I’ll send the calendar invite now. Can you check and accept while we’re on the line?”

Add light qualification

Even if meetings are booked, get small nuggets of context:

➤ “What caused you to reach out?”

➤ “What made this relevant now?”

This gives your AE background without slowing things down.

Guard against spam issues

Sending many outbound emails puts you at risk of getting flagged.

Avoid this by:

âś± Warming up domains before scaling outreach

âś± Targeting focused lists of high-value accounts

âś± Skipping attachments in first-touch messages

âś± Mailing custom notes instead of generic blasts

Don’t confuse being asked to “pitch” with permission to oversell.

Leverage by going into discovery and controlling the proper meeting.

Align selling features to customer needs

Matthew Putnam shows why most people fail the classic “Sell me this pen” test: they pitch the pen instead of the person. The move is to run discovery just like in SaaS sales:

Step 1: Understand your customers

Don’t just explain features.

Ask questions for context.

➤ “Do you find yourself using pens more often?”

➤ “What’s your current workflow for [problem]?”

➤ “Who else has been involved in this process?”

Uncover their value perception, and decision drivers.

Step 2: Show problems and objectives

Find friction that really matters most.

  • Smudged ink or cheap-looking pens

  • Lost sales revenue, compliance risks

  • Frustrated teams and isolated datas

No pain or goals= no sales closed.

Step 3: Present solutions as necessity

Connect your features directly to business needs.

❖ Pen: “Quick-dry ink and sleek design, perfect for signing in front of clients.”

❖ SaaS: “Our platform integrates with your CRM, saving reps hours weekly.”

Frame everything around them, not your product.

Step 4: Build urgency around decision

âś± Scarcity for pens might be limited stock.

âś± Urgency revolves around missed outcomes:

“If this isn’t solved this quarter, you’ll miss your Q4 forecast.”

âś± Urgency is business-critical, not artificially made.

Step 5: Close with your prospect

For selling pens, make them experiment with your product.

For SaaS, guide your clients throughout the buying process:

âž” Consensus building

âž” Procurement and legal

âž” Implementation timeline

Help your prospect take the next steps by closing deals.

TO-GO

James Bissell: Video message that actually land prospects

Chris Ritson: Relevant emails outperform high conversions

Brian LaManna: Shorten ramp time with pipeline obsession

Kyle Asay: Never drop your leverage after internal discussions

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QUOTE OF THE DAY

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"Prospecting is an investment in your future pipeline, not today’s quota."

Anthony Iannarino

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