Jay Schwedelson has tested over 15 million subject lines through SubjectLine.com and sends roughly 6 billion emails a year through his agency. That kind of volume produces something rare in marketing: actual data on what moves open rates, click-throughs, and deliverability — instead of opinions and outdated “best practices.”

On this episode of the Stay Paid podcast, Jay broke down the small tactical moves that produce real lifts in performance — the ones most agents and advisors are sleeping on, and the so-called rules that turn out to be myths from the 1980s.

If your emails aren’t getting the engagement you expect, there’s a strong chance the issue isn’t your offer or your copy. It’s a handful of tactical decisions you’ve probably never thought about.

The Subject Line Is the Only Thing That Matters (Until It Isn’t)

“You write the most amazing email,” Jay says. “You think it’s the greatest copy, the greatest offer. But if you don’t get the email opened, who cares what’s in your email?”

That’s why subject lines deserve more attention than most marketers give them. And the data Jay’s collected on what actually drives opens runs counter to a lot of conventional wisdom.

First, recognize that nobody reads the entire subject line. Recipients scan the first few words, the first few characters — and decide in milliseconds whether to open. That means the start of your subject line is the most valuable real estate in your entire email program.

Two small changes to that opening have a measurable, repeatable impact:

• Start with a number (e.g., “4 hottest listings in your area”) — lifts open rates by approximately 15%
• Capitalize the first word entirely (e.g., “NEW listing on Maple Drive”) — lifts open rates by approximately 20%

These aren’t gimmicks. They work because they break visual monotony in a crowded inbox where every other subject line looks roughly the same.

The Five Subject Line Tactics That Actually Work

Across the 15 million subject lines Jay’s tested, five categories consistently outperform everything else.

1. Curiosity and questions

“Did you hear about the sale in your neighborhood?” “Do you want to know what your home is worth?” Question-based subject lines create an open loop in the reader’s brain — and most of us can’t resist closing the loop. Curiosity is one of the strongest forces in inbox engagement.

2. Urgency and FOMO

“This house won’t last long.” “2 days left.” “Just hit the market today.” Urgency is the single most reliable driver of subject line engagement. The trick is making it specific and real — not manufactured. A real deadline beats a fake one every time.

3. Lifestyle personalization (not name personalization)

First-name personalization — “Hey Jay, check out this listing” — is dead. Recipients see right through it, and Jay calls it “old school garbage.” What works is geographic and lifestyle personalization: dropping in a zip code, neighborhood name, or interest signal that tells the reader you understand who they are.

“Perfect for golf enthusiasts.” “Great community for DIYers.” “Grandparents love this neighborhood.” When you tell someone who they are, they want to engage. Faster than you’d think.

4. The two-word subject line

Try sending an email with a subject line that’s only one or two words long. Forget what those words are for a moment — visually, your email becomes a wall of white space surrounded by everyone else’s cluttered subject lines. It stands out instantly. This is a tactic almost no one uses, which is exactly why it works.

5. The absurdly long subject line

The opposite play also works. Fill the entire subject line bar. Yes, it’ll get cut off. That’s the point. A subject line that’s clearly longer than every other one in the inbox will stop the scroll for the same reason a two-word line does — it breaks the pattern.

“You’re trying to do marketing,” Jay says. “Every time you hit send, ask yourself: what am I doing to have my email stand out and not everybody else’s?”

Don’t Sleep on Emojis (But Use Them Strategically)

Emojis aren’t as novel as they used to be, but here’s the data point most marketers don’t know: less than 5% of all email subject lines use them. That means 95% of your competition is leaving the visual impact of an emoji on the table.

A small house emoji at the start of a real estate subject line still moves the needle. The newer tactic Jay’s seeing perform well is “bookend emojis” — placing the same emoji at the start and end of the subject line. It frames the message visually and stops the scroll.

The Two Body Copy Secrets Most Marketers Sleep On

Once the email is open, two specific tactical moves drive measurable lifts in click-through rate. Most marketers either don’t do them or do them wrong.

Write call-to-action buttons in first person

When you want a recipient to register for an event, what does your button typically say? “Register.” That’s the action you want them to take — it’s a commitment they have to make. It’s not a benefit to them.

Switch to first-person framing and click-through rates jump by approximately 20%. Instead of “Register,” write “I want in” or “Save my spot.” Instead of “Download,” write “Send it my way” or “I need that!”

Nobody consciously thinks “this button is amazing” — but in that millisecond of decision-making, first-person language makes the reader feel slightly more invested in the action. Twenty percent more invested, on average.

Add a P.S. line with a link

Nobody reads your email all the way through. They read the headline, scan a bit, maybe glance at a bullet — and then their eyes go straight to the bottom. If you don’t have a P.S. line at the bottom of your email with a link to your offer, you’re leaving roughly 15% additional click-throughs on the table.

Every email you send should end with a P.S., and that P.S. should restate your core call-to-action with a link. It’s free real estate.

How Long Should the Body of Your Email Be?

It depends entirely on who you’re emailing.

• Brand new contacts: Less than 75 words. They don’t know you. They don’t care yet. Long copy gets deleted.
• Existing clients or engaged prospects: 150–200 words is the sweet spot. They’ve bought into you, so they’ll read more — but don’t push it.

The Frequency Myth That’s Quietly Killing Your Deliverability

If you’ve ever cut back on email frequency because “we’re sending too much,” Jay says you’ve probably made things worse — and you might not even realize it.

Modern email deliverability is engagement-based. Receiving infrastructure (Gmail, Outlook, etc.) decides whether your emails go to the inbox or the spam folder largely based on how often your messages get opened and clicked. The less frequently you send, the less engagement data the system has — and the easier it becomes to land in spam.

“If you’re not sending out at least a weekly email, you have no shot of staying in the inbox,” Jay says. “You’re not going to generate enough engagement with your recipients to look like you’re an ongoing active sender.” (For agents wondering how to maintain that cadence without feeling spammy, our guide to combining mail, email, and social into one follow-up sequence shows how the channels reinforce each other.)

More good news: spam trigger words are largely a myth. The idea that the word “free” or “$$” sends you to the spam folder is outdated by decades. You don’t go to spam because of words. You go to spam because of low engagement.

Unsubscribes Are Good — Spam Complaints Are Bad

Many businesses cut back on email frequency the moment unsubscribes spike. Jay argues that’s exactly backwards.

Unsubscribes don’t hurt your deliverability — they help it. More than 95% of people who unsubscribe haven’t opened or clicked one of your emails in the past six months anyway. They were dead weight on your list, dragging your engagement metrics down. Letting them go improves your sender reputation, not the other way around.

What you actually want to monitor are spam complaints. Those are the metric that hurts deliverability. If your spam complaint rate is climbing, that’s a real signal something’s off — either your audience didn’t opt in cleanly, or your content isn’t matching the expectation you set when they subscribed.

The Most Important Email You’ll Ever Send (Especially in Service Businesses)

For real estate agents, financial advisors, insurance professionals, and other service-based businesses, Jay shared the single highest-leverage email in your entire program: the very first one you send to a new contact.

Here’s why it matters so much. When you send a first email to someone new, your sending infrastructure and their receiving infrastructure are essentially having a private conversation. If the recipient opens, clicks, or engages, the receiving system flags you as a sender they care about — and your future emails are roughly 85% more likely to land in their inbox going forward. If they don’t engage, you’re flagged as low-priority and start sliding toward the junk folder before you’ve even built the relationship.

The mistake almost every service business makes: they treat the first email as an immediate sales pitch. New listing. New product. New offer. The recipient deletes it. The infrastructure logs the non-engagement. Every email you ever send to that person from that point forward fights an uphill battle.

Instead, that first email should establish you as a thought leader and a useful resource — not a sales pitch. Share something genuinely valuable: “I did some research in your area and home values are up 30% over last year. Here’s an article about a renovation trend boosting prices.” Ungated. No form. Pure value. (We dig into why this approach builds trust faster in how educational content moves you from agent to advisor.)

The point isn’t to convert on the first send. The point is to lay infrastructure groundwork so every email afterward has a fighting chance.

Gmail Tabs Aren’t the Enemy You Think They Are

Plenty of marketers panic when their emails land in Gmail’s promotions tab instead of the primary inbox. Stop panicking. The data tells a different story:

• Less than 25% of Gmail users have tabs enabled in the first place
• Of those who do, about 50% check the promotions tab every single day

Jay’s analogy is perfect: “When you click on the promotions tab, you’re not there by accident. You’re not lost. You’re there intentionally.” It’s not the junk folder. It’s more like the mall — people who land there are in buying mode, research mode, comparing-options mode. That’s exactly the headspace you want your audience in when they see your offer.

Buying Email Lists: The Truth Nobody Says Out Loud

Conventional wisdom says you should never, ever buy an email list. The reality, according to Jay: every major brand on the planet buys lists, even if they swear up and down that they don’t.

If you’re going to buy or import a list, here’s the non-negotiable step almost no one takes: run it through a list validation service before you hit send. Tools like ZeroBounce, NeverBounce, or Webbula will eliminate roughly 95% of the dangerous addresses on a typical list — spam traps, habitual complainers, dead inboxes that drag down your sender reputation.

It costs almost nothing to run, and it can be the difference between a successful first send and torching your sender reputation for months. Jay recommends running this not just on imported lists, but also annually on your entire database to keep the list clean over time.

Stop Comparing Yourself to Industry Averages

“Industry averages drive me crazy,” Jay says. “Different brand, different database, different timing, different offer, different everything. It’s like — what are we comparing?”

Instead of trying to beat some vague “30% open rate is the industry average” benchmark, beat yourself. Bucket your emails by category — newsletters, transactional emails, onboarding sequences, offer-based emails — and benchmark each category against its own historical performance.

Last quarter your newsletter had a 32% open rate. What are you doing to push that to 35% this quarter? That’s a useful, actionable benchmark. “Are we above industry average?” is not.

FAQ: Email Marketing for Agents and Advisors

Should I use AI to write my email subject lines?

Jay says AI is great as an editor, terrible as an idea starter. The problem with starting from AI: it generates the same generic output for everyone, creating “a tidal wave of generic garbage.” Use AI to enhance copy you’ve already drafted — make it more urgent, add FOMO, tighten — but don’t let it generate from scratch. (Related: why AI can’t fake your voice and how to keep your marketing recognizably human.)

How often should I email my list?

At minimum, weekly. Less than that and you risk slipping out of inbox placement entirely because your overall engagement signals to receiving infrastructure look weak.

Will spam trigger words like “free” send my email to the junk folder?

No. Spam trigger word filtering is largely a myth from the 1980s and 90s. You go to spam because of low engagement, not because of word choices.

Is it bad if my emails go to the Gmail promotions tab?

Not really. Less than 25% of Gmail users have tabs enabled, and the ones who do treat the promotions tab as their dedicated shopping/research space. There’s no significant performance penalty for landing there.

How do I segment my list if I don’t have a lot of data on my contacts?

Use click-based segmentation. Tag your email links so you can capture what each contact is interested in based on what they click. Over time, you build rich segments without ever asking your audience to fill out a form.

What’s the easiest tactical change I can make to my next email?

Two options: capitalize the first word of your subject line, or start it with a number. Either change tends to lift open rates by 15–20% with zero additional effort.

Take Action: Pick One Tactic and Test It This Week

The difference between marketers who consistently grow their lists and the ones who plateau isn’t access to better tools. It’s the willingness to test small tactical changes, measure the lift, and stack the wins. Pick one of the tactics above — capitalized first word, first-person CTA, P.S. line, two-word subject line — and run it on your next send. See what happens.

Want more from Jay? Watch the full Stay Paid episode on YouTube, rate your next subject line free at SubjectLine.com, or subscribe to Do This, NOT That: Marketing Tips with Jay Schwedelson for more tactical breakdowns.

If you want to make every email you send more valuable, our guide to repurposing content across email, social, and print shows how to turn one strong piece of content into a month of touchpoints — without burning out your creative time.

And if writing weekly emails feels like one more thing on a plate that’s already full, ReminderMedia’s Digital Marketing Platform handles the hardest part for you — done-for-you digital magazines, local events newsletters, and branded posts sent automatically to your database every month. It gives you the consistent send cadence that protects your deliverability and the high-quality content that earns the open. Because the best subject line in the world only works if there’s something worth sending behind it.