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Recently, a tech founder reached out after his SaaS company hit a growth plateau.

His business was doing $540K in revenue from inbound and referrals, but new leads were slowing down and he needed more predictable pipeline.

So he wanted to try outbound sales, something he had zero experience with.

THE CHALLENGE:

We jumped on a call and I heard a classic founder's dilemma:

I asked my typical questions around hiring plans, growth targets, and who would be responsible for the outreach - but instead of suggesting they build a comprehensive playbook and process, I recommended a different approach.

Me: "try outbound yourself for two weeks.”

Them: (skeptically) "I don't have time for that."

Me: "that's why it works, the time constraint will force you to be strategic.”

So we launched a 14-day sprint. It worked well, so we expanded to 30 days.

Here's the foundation of the playbook:

THE 30-DAY OUTBOUND FOUNDATION:

1. Reverse Prospecting Method

What is it: A blueprint that uses existing customers to find new prospects

1. Identify Common Traits: Find the hidden patterns in your customer base:

   • Who funded them?

   • When did they buy?

   • What risks drove urgency?

   • Which exact problems got solved?

   • Who are their competitors?

2. Build Your Target List: Target these high-conversion segments:

   • VC portfolio companies

   • Direct competitors

   • Mutual connections

   • Leadership connection points

3. Personalize Based on Connections: turn cold to warm by referencing shared investors, similar challenges, or mutual connections.

Quick win: use a tool like ZoomInfo to help automate this process.

2. The 10 Account Rule

What it is: A hyper-focused approach that rejects volume in favor of quality.

1. Hunt for Buying Signals: 

   • Fresh funding rounds

   • Leadership shake-ups

   • Expansion announcements

   • Hiring spikes

   • Competitor moves

2. Decode at Three Levels: 

   • Company DNA

   • Department friction

   • Decision-maker priorities

3. Create Your Messaging: more on this below.

Quick win: copy and paste this prompt into GPT to help with your outreach.

3. Use “Problem Based” Messaging

What it is: Messaging that speaks to pain, not features.

How to use it (email framework):

1. Sentence 1: reference a common challenge related to persona

2. Sentence 2: responsibilities/obstacles that often get in the way

3. Sentence 3: simple phrasing of what you do / how you help

4. Sentence 4: desired outcome you can help them achieve

5. Sentence 5: casual call to action

Quick win: use a template the like these or the one below.

Want Help with Outbound?

Not every founder has the time for DIY outbound, even for 30 days.

If implementing this framework feels overwhelming, I can help in two ways:

Option 1: Outbound Audit & Strategy
I'll assess your current approach and build a custom outbound playbook for your specific market. You'll get my exact templates, research framework, and execution checklist tailored to your business.

Option 2: Results-Only Outbound
Got the strategy and looking for a team to execute for you? I can connect you with a fractional BD agency who work on a performance basis. You only pay for results.

Until next Thursday,

TSG

P.S. I reply to all emails.