Stop Sabotaging Your Pitch: 5 Email Hygiene Mistakes Founders and Sales Reps Make

These small errors kill your credibility

Whether you’re a sales rep pitching a retailer, a founder pitching an investor, or a supplier pitching a distributor—too often, your message is killed by bad email hygiene.

Here are 5 things you probably aren’t considering when you hit send on that deck or portfolio:

• File Size: Keep attachments under 5-10MB. Your 45MB deck is bouncing off their corporate firewall. Use compression or a secure link (like a Google Drive/Dropbox view-only link) instead. 💾

• File Name: Avoid names that only abide by your internal logic like “Deck_FINAL_v3_NEW.pdf.” Use descriptive names like “BrandName_PitchDeck_Nov2025.pdf.” This makes their filing and search easier. 📂

• The Ask: Never attach a document without an ultra-specific reason. The email body must contain your 1-2 line thesis before they open the file.¹ 🗣️

• Format: Send documents as a PDF. Never a PowerPoint (.ppt) or an Excel (.xlsx). Assume they don’t have the software, fonts, or are using a phone. 📱

• Tracking: Send a link (not an attachment) via a service like DocSend that allows tracking. Knowing when they open it is your best follow-up signal. 👣

Your delivery is part of your brand. Treat your email as seriously as your liquid quality.

1. For more on business writing, check out The Pyramid Principle: Logic in Writing and Thinking by Barbara Minto. Minto’s method teaches the presentation of the conclusion first, followed by the supporting arguments. This ensures that even if the recipient only reads the first two lines of your email, they grasp the main point immediately—the essence of pitching in under two minutes.

For more on email hygiene, Anne Janzer’s marvelously succinct 33 Ways Not to Screw Up Your Business Emails is a great place to start.