Mastering B2B Email Marketing: How to Write Subject Lines That Convert and Click-Through Strategies That Drive Results – A Conversation with Jay Schwedelson

Marketing

Mastering B2B Email Marketing: How to Write Subject Lines That Convert and Click-Through Strategies That Drive Results – A Conversation with Jay Schwedelson

Marketing

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your email open rates, click-through performance, and lead quality without annoying your prospects or wasting time on outdated tactics.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Jay debunked the outdated myth that there are “spam trigger words” like free, save, or discount that tank your deliverability.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.”

Marketing

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)

Marketing

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.”

Bonds

Maximizing Revenue with Surety Bonds and Niche Contractor Insurance Strategies

The middle market commercial insurance landscape is evolving at a rapid pace. Agencies that once relied solely on traditional property and casualty products are now discovering untapped revenue streams by embracing surety bonds and specialty coverages. By understanding how to position niche products—such as drone insurance for contractors—alongside licensing and permit bonds, agencies can capture high-intent leads, accelerate earned premium, and foster deeper client relationships.

In this post, we’ll explore a comprehensive bonding-first growth strategy: from the fundamentals of surety bonds to advanced marketing funnels, partner ecosystems, and actionable implementation checklists. Whether you’re a seasoned producer or a rising agency principal, you’ll walk away with a playbook to maximize revenue, differentiate your brand, and become the go-to resource for contractor clients.

Read More »
agencies

Reclaiming Time and Building Efficiency: How Technology is Reshaping Insurance Servicing and Agencies Growth – A Conversation with Colby Tunick

In the world of independent insurance agencies, servicing existing policies often overshadows the pursuit of new business. It’s estimated that 80% of agency time is spent servicing renewals rather than generating new opportunities. With the average cost of servicing a policy renewal totaling around $135 per policy, agencies are dedicating significant resources simply to maintain the status quo.

This servicing burden presents a major scalability problem. For every thousand policies on the books, agencies are effectively employing two full-time account executives just to keep up. The result is a “tyranny of insurance” where agency growth becomes harder as success increases. This challenge is even more pronounced for agencies focused on the middle market or attempting to backfill their books with small commercial insurance and personal lines.

Scaling a book of business while trapped in administrative quicksand isn’t just inefficient; it’s unsustainable. Agencies need a way to break free if they hope to thrive in today’s competitive and evolving market.

Read More »
Data

Maximizing Middle-Market Workers’ Compensation Success: Data-Driven Prospecting, Compliance Wedges, and Claims Excellence

Middle-mazrket businesses face unique challenges when it comes to managing their workers’ compensation programs. Unlike large enterprises, they often lack dedicated in-house resources for safety, compliance, and claims oversight; yet unlike small businesses, their scale subjects them to more sophisticated regulatory scrutiny and larger potential losses. In this environment, commercial insurance producers who master an integrated approach—combining precise prospecting data, impactful compliance applications, and exceptional claims handling—can both win new accounts and build lasting client relationships.

Read More »
Market

Strategic Market Access for Independent Agencies: Unlocking Growth, Stability, and Profitability

In the most challenging insurance market many of us have ever seen, independent agencies are grappling with a familiar foe: limited carrier access. Whether you’re a former captive agent trying to break into the independent space or a small agency trying to grow your commercial book, the obstacles are real. Direct appointments are hard to come by, especially for shops under $5 million in revenue, and wholesale markets can feel intimidating or like a last resort.

But they don’t have to be. With the right partner, wholesale and brokerage relationships can become a strategic advantage, not just a stopgap. This post explores how agencies can leverage smart market access to grow confidently, preserve profitability, and position themselves for long-term success.

Read More »
Remote

Building High-Performing Remote Insurance Teams: Core Values, Hiring, Onboarding & KPI Strategies

The insurance industry is undergoing a profound transformation as middle-market agencies recognize the benefits and challenges of embracing a fully remote workforce. No longer viewed as a temporary workaround, remote models offer the potential to tap into nationwide and offshore talent pools, reduce overhead, and increase flexibility in an increasingly digital world. Yet, flipping the switch to virtual operations can expose gaps in documentation, dilute corporate culture, and strain traditional oversight mechanisms. In this post, we’ll explore the four pillars essential to building a high-performing remote insurance team—core values, hiring practices, onboarding processes, and KPI strategies—while also delving into best practices for managing domestic versus offshore employees, ensuring data security, leveraging productivity tools, and fostering trust and autonomy.

Read More »
Captive

Captive Insurance Strategies for Middle Market Success: Empowering Independent Agents with Risk Control and Profitability

In today’s hard commercial insurance market, middle market business owners are more open than ever to solutions that give them greater control over their insurance costs. While guaranteed cost programs remain the default option, they often lack the flexibility and long-term savings that high-performing businesses crave. That’s where captive insurance comes in—a powerful but often misunderstood tool that enables clients to turn insurance from a sunk cost into a strategic asset.

Read More »

Responses

Related Articles

Why Most Salespeople Fail: Mastering the Mindset, Process, and Power Dynamics of Professional Selling

The truth about professional sales isn’t flashy, and it certainly isn’t about charisma. If you think selling is about having the “gift of gab,” winging it on calls, or leaning on your likability to win deals, you’re doing it wrong—and that’s why you’re struggling. In this post, we’re breaking down lessons from a brutally honest conversation with Benjamin Dennehy, the UK’s Most Hated Sales Trainer®, about why so many producers in commercial insurance and other industries fall short—and what the top performers do differently.

Killing Commercial Login