127: A New Marketing Strategy Inspired by Olive & June
Feeling like your sales or emails have gone a little stale? In this episode, Heather talks about the experiments she’s running this season to breathe new life into her business. She’s ditching the copy-and-paste sales strategies, and questioning everything from why her emails land in the promotions tab to whether hitting “duplicate” is secretly tanking deliverability. Inspired by one of her favorite brands, Olive & June, she’s trying out a fresh new strategy and inviting you to follow along! This season is all about trying new things, learning as you go, and proving that growth comes from experimenting, reflecting, and refining!
Key Takeaways:
- (02:30) Why Thanksgiving products get less attention and how she’s planning her seasonal sale
- (06:30) Repeating sales year after year; why business emails are landing in promotions
- (12:40) The Olive & June marketing strategy
- (14:55) How a “free gift with purchase” can boost value without lowering prices
Episodes Mentioned:
#121: Inside Heather’s High-Converting Funnel
#126: How to Plan the Rest of 2025 and Finish the Year Strong
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Trying New Marketing Strategies: New Approaches to Pricing, Gifting, and Email Marketing
If you’re a teacher building an online business, you’ve almost certainly seen it: the endless scroll of business gurus promising secret systems and sure-fire formulas. The reality for most of us isn’t so straightforward.
We’re “in the trenches”—experimenting, learning, and, most importantly, sharing what’s actually working (and what isn’t).
This episode is a candid, behind-the-scenes look at innovative strategies you can use in your own teacher business, with a special focus on fresh approaches to email marketing and campaign creativity.
Embracing Change: Why Routine Can Stall Growth
Like many business owners, Heather found herself repeating past successes year after year: “for most of my products, the first time I sold them…they did well, so I thought if I could just repeat that over and over, I’ll be just fine.”
But in the digital world, especially with inbox algorithms constantly shifting, what worked last year might not cut it this year.
If you’re using the same sales emails or barely tweaking old messaging, watch out—your emails will likely land in Gmail’s “Promotions” tab, out of sight (and out of mind) for most subscribers.
This is a reminder that innovation is essential, both to keep things interesting for your audience and to outsmart ever-smarter tech filters.
Inbox Visibility: The Hidden Power of New Broadcasts
One of the most valuable insights from Heather’s journey is about email deliverability. She explains how hitting “duplicate” on old emails—even when you edit the content—can signal to algorithms that it’s the “same old, same old.”
Her experimentation? Start each campaign by hitting “new broadcast” and writing from scratch, even if it’s just rewording older content. Change up subject lines, shuffle your emoji placement, or swap out keywords.
Yes, it’s extra work. But it may make all the difference for where your email lands. And with most teacher audiences using Gmail, every little bit counts when trying to break through that Promotions filter and into the main inbox.
Pro tip: Heather subscribes to her own lists on several email accounts (including her personal and business inboxes) to monitor exactly where her campaigns land. Consider doing the same so you know what your subscribers actually see!
Looking Beyond Discounts: The Free Gift with Purchase Strategy
If you’re tired of endlessly lowering your prices to entice buyers, you’re not alone.
Heather admits, “we can discount all day long and it’s a slippery slope; the price can always go lower.” Instead, she urges teacher business owners to try value-adding strategies inspired by successful brands outside of the education niche.
Take Olive & June, a nail polish business that’s mastered marketing not just with discounts, but with gifts. Their “free gift with purchase”—often an exclusive item—creates urgency and excitement without cheapening their product.
For her Thanksgiving activity pack, Heather borrowed this approach, offering a “friends” themed digital activity pack (which cost her nothing to distribute) as a free bonus. The goal? Raise the perceived value without racing to the bottom on price.
Digital products make this particularly powerful. Unlike physical businesses, your “gift” is virtually free to provide—meaning happy customers and healthy margins.
Lessons in Iteration: Testing, Tracking, and Tweaking for Success
Perhaps the central message is this: don’t give up on a new strategy if it doesn’t work perfectly the first time.
Heather is candid—she’s waiting to see if her free gift increases conversions, and plans to test it again for Black Friday with a fresh bonus item.
Shifts in your tactics, from how you send emails to what extras you provide, can take time to show results.
The key is tracking outcomes, reflecting, and adjusting until you find that sweet spot.
Building a teacher business online is a journey—one best fueled by experimentation, reflection, and a bit of courage to try what others aren’t.
Whether tweaking your email tactics, tracking deliverability, or adding irresistible value instead of discounts, the opportunities are endless.
Ready to start your own teacher biz? Grab the free Teacher Biz Starter Guide and take the first step toward a business that brings both freedom and fulfillment.