Mastering B2B Email Marketing: How to Write Subject Lines That Convert and Click-Through Strategies That Drive Results – A Conversation with Jay Schwedelson
Mastering B2B Email Marketing: How to Write Subject Lines That Convert and Click-Through Strategies That Drive Results – A Conversation with Jay Schwedelson
If you’re in commercial insurance sales or B2B marketing, chances are you’ve dabbled in email outreach. And if you’re like most, you’ve probably concluded that email doesn’t work anymore. But what if the problem isn’t the channel—it’s the way you’re using it?
In a recent episode of the Power Producers Podcast, I sat down with Jay Schwedelson—founder of SubjectLine.com and CEO of Outcome Media—to break down what’s working in email marketing today. With 6 billion emails sent annually through his agency, Jay doesn’t just talk trends—he builds pipelines with them.
This post dives deep into the actionable strategies Jay shared that you can use to dramatically boost your email open rates, click-through performance, and lead quality without annoying your prospects or wasting time on outdated tactics.
Why Email Marketing is Still Your Most Powerful Sales Tool
Despite the rise of social media, SEO, and video, email remains the most controllable, direct line of communication between you and your prospects. As Jay put it:
“Your email database is the most important asset in your company. It’s the only thing you truly control.”
Unlike social media platforms that throttle reach with algorithms or paid ads that depend on daily spend, email lets you control when and how your message is delivered. It’s the foundation of surround-sound marketing, where you’re staying top-of-mind through multiple touchpoints—social, search, and email—all working in concert.
For commercial insurance producers, especially those writing middle market accounts, this is your long game: deliver value consistently, so that when a prospect is in-market, your name is already in their brain.
The Subject Line Is Your First Close: How to Get the Open
Let’s be blunt—if your subject line doesn’t land, the rest of your email doesn’t matter. Most B2B buyers are doing a “social scroll” through their inboxes. You’ve got milliseconds to earn their attention.
Jay debunked the outdated myth that there are “spam trigger words” like free, save, or discount that tank your deliverability.
“The reason you’re in spam isn’t your subject line. It’s engagement. You can use emojis, caps, brackets—whatever works to catch attention.”
Tactical subject line tips:
- Start with a number: Ex: “7 Ways to Cut Commercial Auto Premiums”
- Use ALL CAPS for your first word or two: Ex: “NEW Risk Trends in Hospitality”
- Use brackets: Ex: “[Free Guide] Workers’ Comp Mod Explained”
- Industry/job function personalization: Ex: “For Property Managers in Tampa”
- Use curiosity & questions: Ex: “What’s Driving 2025 Rate Increases?”
- Company name trick: Ex: “Is [CompanyName] Paying Too Much for Insurance?”
Want to test how your subject line stacks up? Use SubjectLine.com, a free tool Jay built that analyzes over 15 million tested lines.
Clicks Are King: Writing Body Copy That Converts
Once you win the open, it’s time to keep them reading and clicking.
Email structure that works:
- 75 words or less for cold outreach
- 150 words max for warm prospects or clients
- Never more than 4 lines of text per block
- Use bullet points and white space
- Include 1 clear CTA button
- Always include a P.S. with a link
“Email is a chain: delivery → open → headline → click → landing page. Break one link, and the rest falls apart.”
Pro Tip: First-person CTA buttons convert better
Instead of:
- “Register Now”
Try:
- “Save My Spot”
- “I Want In”
- “Download My Copy”
These subtle shifts in language create a sense of ownership and action for the reader.
Frequency vs. Relevancy: Getting the Email Cadence Right
A common fear among producers is emailing too often. But Jay argues the real issue is not emailing enough.
“If you’re not sending at least five emails per month, you’re hurting your inbox placement. You need engagement to stay visible.”
Key points:
- More frequent email = higher engagement = better deliverability
- Unsubscribes are not bad—they’re signs you’re reaching the right people (and refining your list)
- Spam complaints (not unsubscribes) are what actually hurt you
- Don’t fear the promotions tab—it’s part of the inbox and is often checked by people ready to buy
The takeaway? Send relevant content often and consistently. That’s how you stay in the game—and in the inbox.
Campaign Tactics That Build Authority (and Pipeline)
Great email marketing isn’t about spamming your list with requests to “book a call.” It’s about thought leadership and value-first marketing.
What you should be sending:
- Weekly insights: “3 Things Contractors Need to Know This Week”
- Industry news: “Breaking: New Legislation Affecting Property Managers”
- Educational content: “How to Avoid Mod Audit Surprises in 2025”
- Offers with urgency: “This Ebook Expires in 3 Days”
“If you let content live on your website forever, people feel no urgency. Take it down temporarily to create FOMO.”
Rename your webinars to things like:
- “Insider Session”
- “Live Risk Panel”
- “Executive Briefing”
Those terms perform better than “webinar,” which Jay calls a “stained word” that signals boredom and low value.
Performance Metrics That Actually Matter
So how do you know if your emails are working?
Open rates
Yes, they’re inflated (thanks, Apple Mail privacy), but they’re still directionally useful.
“If A/B testing shows Subject Line A gets a 35% open rate and B gets 22%, A wins. Even if the real numbers are off.”
Click-through rates
Also suffer from bot interference but are useful for measuring relative performance.
Jay’s Pro Tip: The 2 AM Bot Test
- Send an email at 2 AM
- Check open/click activity in the first 30 minutes
- Anyone engaging then? Likely bots
- Use this to baseline your false opens/clicks
Stop chasing industry benchmarks
Instead, benchmark your own sends by category:
- Newsletters
- Event invites
- Cold outreach
- Promotional offers
Your goal: improve vs. your past self, not vs. generic industry stats.
Final Thoughts: The Future of Email Marketing for Commercial Insurance Producers
If you’re a producer writing middle market commercial insurance accounts, there’s a golden opportunity in front of you. Most of your competitors are either not using email at all—or using it poorly.
This gives you the chance to stand out, build authority, and create demand before your prospects are ready to buy.
Start by:
- Testing your subject lines
- Structuring your body copy for skimmability
- Writing in first person
- Sending more frequent, value-first emails
- Creating urgency with content expiration
- Benchmarking yourself, not others
And remember:
“When you send more, more things happen.”
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