The Wingman Blog

Practical advice on sales systems, delegation, and growing past founder-led sales β€” written for agency owners and service founders.

All Posts Sales Systems Hiring & Training Bootstrapped Tools Founder Stories Scripts & Playbooks
πŸ’° Bootstrapped Tools

The $18 Sales Stack: A Step-by-Step Guide

Most founders think they need a $200/month CRM and a fancy tool stack to close deals. They don't. Here's the lean setup that gets results without the bloat.

February 17, 2025 Β· 7 min read Β· Read the article β†’

More articles

πŸ”„ Sales Systems

How to Fix a Stagnant Sales Process

The gap between founder-led sales and a scalable operation is one of the hardest transitions. Here's how to spot the warning signs and reset.

Nov 20, 2024 Β· Read β†’

🎯 Sales Systems

The Top 3 Sales Mistakes Agency Founders Make

Sales should be a structured, repeatable process β€” not a constant grind. Check if you're making one of these three mistakes.

Nov 20, 2024 Β· Read β†’

🎯 Sales Systems

Why Your Sales Process Only Works When You're On the Call

The most common reason founder-led sales doesn't scale β€” and what to do about it.

Jan 28, 2025 Β· Read β†’

πŸ“ž Scripts & Playbooks

The 5 Objections Every Agency Owner Hears β€” and How to Handle Them

Word-for-word responses to the pushbacks that are costing you deals right now.

Jan 14, 2025 Β· Read β†’

πŸ§‘β€πŸ’Ό Hiring & Training

How to Know When You're Actually Ready to Hire a Sales Rep

Hiring too early kills close rates. Here are the signals that tell you it's the right time.

Dec 10, 2024 Β· Read β†’

πŸ—ΊοΈ Sales Systems

How to Build a Sales Process Map in an Afternoon

A simple framework for documenting your sales process before handing it off.

Nov 22, 2024 Β· Read β†’

πŸ’¬ Scripts & Playbooks

Discovery Call Scripts That Actually Convert (With Templates)

The exact structure we use with clients to run discovery calls that close at 40%+.

Nov 5, 2024 Β· Read β†’

πŸ“ˆ Founder Stories

How One Agency Owner Went From 100% of Sales to 20% in 90 Days

A behind-the-scenes look at how we helped one founder finally step back from the sales floor.

Oct 18, 2024 Β· Read β†’

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