Issue #31: Writing Subject Lines That Get Opens, New Picture-in-Picture Feature HubSpot Academy, and the HubSpot Cacheflow Announcement

76.33.

This number has lived rent-free in my head for years. It’s the average lifespan of an American male.

It’s the number that inspires me to obsessively cross things off my bucket list.

So, when my favorite band (who also happens to be some of my best friends) invited me to hop on the bus with them to hang out for a 10-day tour, I said, “Heck yes!”

Last week, I watched them play to sold-out crowds in New York City, Providence, Toronto, and Montreal and had one of the best weeks of my life.

Forgive me for getting existential, but life is short. Do fun things with the people you love. Hop on the bus!

In today’s issue of WIN-Bound Weekly, we’ll cover:

• 10 proven strategies for subject lines that actually get opened—spoiler alert: ditch the clickbait!
• HubSpot’s brand-new Picture-in-Picture mode for Academy training videos. If you’re a multitasker, you’ll love this feature.
• HubSpot’s latest acquisition of Cacheflow and what it means for your sales process—think faster quotes, smoother invoicing, and even better revenue management.

Let’s get into it!

10 Proven Strategies for Writing Subject Lines That Get Opened (and Why You Should Ditch the Clickbait)

It’s first thing in the morning and you’ve just sat down at your desk.?

You take the first sip of the Vanilla Sweet Cream Cold Brew you picked up on your way into the office, pull up your inbox, and see an email with the subject line “Re: This week’s meeting”

You don’t recognize the sender and open it to investigate. It turns out to be a sales email, not a real reply.

We have to do better, people - you’re ruining my Cold Brew time, but more importantly you’re ruining your sending reputation in the long term.

Especially when all you have to do to write amazing subject lines is to use these 10 key categories and be inspired by these 20 examples.

Good Marketing Subject Lines:

Create Curiosity - Use intrigue to make your reader want to know more.

Examples:

• Tea Collection: “Are You Ready To Spring It On?”
• Apartment Therapy: “Why You Should Keep Your Clothes in the Freezer.”

Use Personalization - Use the recipient’s name or reference something relevant to them.

Examples:

• LinkedIn: “Tony, people are looking at your LinkedIn profile”
• Vail Resorts: “Come Back This Winter With an Exclusive Deal, Tony”

Highlight Promotions - Capture attention by not only highlighting your offer but also what the reader stands to lose if they don’t open the email.

Examples:

• Thrive Market: “Limited time only: Extra 25% off + FREE gift”
• LL Bean: “Last Day All Slippers 20% off”

Make You Laugh - Nobody on the planet does this better than Jay Schwedelson on GURU Media Hub . Take note, and don’t be afraid to make them laugh.

• Dollar Shave Club: “Open up and say wowie zowie!”
• Brooks Brothers: “Up to 40% off trousers & sport coats. It’s a tailor-made sale.”

Address Pain Points - Address a problem that your audience faces and then offer a solution.

Examples:

• Domino’s: “No address? No problem. Now Domino’s can deliver to over 150,000 Domino’s Hotspots.”
• Vidyard: “Engaging your prospects can be hard. Video makes it easy.”

Re-Engage Readers - Find creative ways to re-spark the reader’s interest.

• Marriott Rewards: “We’ve missed you, Tony! Please come back!”
• The Danger Booth: “Something new (and virtual!) from The Danger Booth...”

Use Emojis - Emojis not only create contrast in the inbox, but they also yield higher open rates.

Examples:

• ClassPass: “Go from ?? to ?? for just $4”
• Hotjar: “Customize your visitor feedback experience ?? ?? ??”

Provide Social Proof - Social proof is the idea that people will adapt their behavior according to what other people are doing.

Examples:

• Patagonia: “Top reviewed styles from customers like you”
• HelloFresh: “Pssst... your friends are cooking up a storm!”

Oh, and of course I can’t forget about my sales peeps. We can do better than a fake reply subject line, try these instead.

Good Sales Subject Lines:

Address a Problem: Work on creating problem-based sales subject lines from various phases in the buyer’s journey that made us want to learn more.

Examples:

• Shopify: “New Guide: How to grow retail during COVID-19”
• WordStream: “5 Tips to Navigate the Sunsetting of Modified Broad Match”

Follow-Up: A lot of sales is about following up after a prospect takes a certain action on your website or signs up for your offer.

Examples:

• GoDaddy: “It's time to upgrade your website.”
• Calendly: “How are you liking Calendly?”

When all else fails, don’t guess - test! Check out tools like this AI Subject Line Tester to help you quickly improve your ideas.

New from HubSpot: Picture-in-Picture for HubSpot Academy

I’m a huge fan of the HubSpot Academy, and so is my team.?

We have a fierce competition raging in the office to see who can rack up the most HubSpot certifications by the end of the year.

Why? Because HubSpot certifications are incredibly valuable. Not only do they teach us how to use HubSpot better, they provide practical lessons on how to do our jobs better as sales, marketing, and customer service folks.

And now, HubSpot has made the HubSpot Academy even better in a recent update.

The Announcement: HubSpot’s New Picture-in-Picture (PiP) Feature for Academy Content

In PiP mode, you can watch Academy courses, lessons, and tutorials in a small, resizable window that stays on top of your screen while you work. No more switching tabs or losing focus—you can now learn while actively using HubSpot.

This means you can follow along in your own HubSpot portal for hands-on learning.

Why HubSpot Users Are Excited:

• A Treat for the Hardcore Multitaskers: If you’re a walk and chew gum kind of person like me, you’ll be able to multitask during your HubSpot Academy lessons.?
• A New Way to Stay Focused: Keep the Academy content visible without having to toggle between screens.
• Customizable View: Resize and move the PiP window wherever it’s most convenient on your screen.
• Beat Your Coworkers In Your Friendly HubSpot Certification Competition: OK, maybe I’m the only one excited about this one.

The best part is this new feature is available across all HubSpot hubs and tiers!

HubSpot’s Acquisition of Cacheflow: What Marketers Need to Know

HubSpot has just announced its acquisition of Cacheflow, a company that specializes in subscription billing and CPQ (Configure, Price, Quote) software.?

This move will have a big impact on HubSpot’s Commerce Hub, by bringing more automation to revenue management and helping businesses shorten the sales cycle.

Why is this important?

Cacheflow’s software will allow HubSpot users to:

• Streamline the quote-to-cash process: This will make it easier for businesses to manage quotes, close deals, and speed up revenue collection.
• Access subscription billing tools: Enabling seamless management of recurring payments and subscription revenue.
• Optimize complex pricing models: Simplifying the process for businesses with more complex pricing and configuration needs.

All within the HubSpot platform!

Why HubSpot Users Are Excited

HubSpot users can look forward to:

• A Smoother Buying Experience: Cacheflow’s CPQ tools allow for faster and more accurate quoting and invoicing, reducing friction in the sales process.
• On a Unified Platform: HubSpot users will now have customer, sales, and payment data all in one system, making it easier to track transactions and renewals.
• Improved Upsell and Renewal Capabilities: Businesses can now leverage better tools to upsell and manage renewals, maximizing revenue opportunities.

What’s next?

Stay tuned here on the newsletter for more updates as Cacheflow’s features become available within HubSpot!