Why Our Best Rep Was Also Our Best Writer: Teaching Sales Teams to Write Their Way to Higher Bookings

How one experiment with newsletters reshaped sales performance and created a 40% lift in demo bookings.

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A Founder’s Lesson From the Sales Floor

When I first asked one of our most promising sales reps to draft a customer newsletter, he looked at me like I had confused him with marketing. But I insisted. Weeks later, the rep who had always been a strong closer became the author of messages that filled our calendar with qualified demo requests. Writing didn’t replace selling—it sharpened it.

According to Harvard Business Review, effective communication is the single most important predictor of sales success. Writing, often overlooked, is the most scalable form of that communication.

The 40% Lift That Changed Everything

After three months of experimenting with rep-written newsletters, demo bookings rose by 40%. The reason was simple: prospects trusted the authentic, human writing from someone actually on the sales team. As McKinsey notes, buyers increasingly value salespeople who communicate with authority and empathy—not just canned scripts.

A Gartner study found that 43% of B2B buyers prefer self-directed learning and content before speaking to sales. If your reps can write content that feels useful—not promotional—they become the bridge between content and conversion.

Writing Prompts That Double as Discovery

We created weekly writing prompts for our reps:

• “If you had to explain our solution to a 10-year-old, what would you write?”

• “What’s one pain point you hear repeatedly this week?”

• “Draft an email that answers the top three objections you got today.”

These prompts weren’t just for writing practice—they sharpened reps’ ability to spot patterns in buyer needs, a skill Forrester calls essential for modern selling.

A “Rewrite Before You Send” Checklist

Reps also adopted a simple checklist before sending any written message:

1. Is it clear who this is for?

2. Does it address a real problem the buyer faces?

3. Can one sentence be cut without losing meaning?

4. Does it sound human, not automated?

As Seth Godin puts it, “People don’t buy goods and services. They buy relations, stories, and magic.” A rewrite is often where the story actually emerges.

Templates That Actually Book Meetings

Instead of long product pitches, reps used short, written templates:

• Follow-up after a demo → A three-line recap + one helpful link + a single call to action.

• Re-engagement → “I thought of you when I saw this trend report. Worth a chat?”

• Newsletter intro → A quick personal take on an industry stat before linking to a resource.

Templates gave structure, but reps still personalized every message. HubSpot data shows that personalized follow-ups can increase reply rates by over 25%.

Why It Matters for Sales Leaders

If you’re a sales leader, the message is clear: writing is no longer a marketing skill alone. It’s a sales multiplier. Training reps to write better is training them to think better. And better thinking leads to better bookings.

Or as Daniel Pink reminds us, “We are all in sales now.” Teaching reps to write is teaching them to sell in a medium buyers increasingly prefer.

Just launched your new business and need resources to ace direct marketing at lower costs with higher ROI?

Check out Salesfully’s course, Mastering Sales Fundamentals for Long-Term Success, designed to help you attract new customers efficiently and affordably.

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