Hey — It’s Nico.

Welcome to Behind Tactics 🧠, the Failory newsletter where I share the strategies behind the best startups.

This issue takes 6 mins to read. If you only have one, here’s what you need to know:

• Remote OK has mastered upselling, turning job posts into a revenue-generating machine with smart upgrade options.

• Their upsells, like highlighted listings and custom branding, give companies tools to stand out while boosting revenue.

• Psychology plays a big role: pre-selected options and loss aversion nudge users to spend more without feeling pressured.

• The strategy works because it creates competition among companies to differentiate themselves, especially through exclusive features.

Let’s get into it.

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The Strategy

This week, we’re diving into how Remote OK has turned job postings into a revenue-generating machine. Remote OK isn’t just another job board—it’s a platform built exclusively for remote work. By focusing on this niche, they’ve established themselves as a trusted resource for companies and job seekers looking for remote opportunities.

What really sets them apart, though, is how they’ve monetized their platform. Instead of relying on a flat fee, Remote OK uses a smart upsell strategy, offering companies a range of optional upgrades to enhance their job posts. These include features like highlighted listings, custom branding, and premium placement—all designed to help companies stand out and get noticed by top talent.

Why does this strategy work so well? What makes companies willing to pay hundreds for features that might be free elsewhere? And what can other businesses learn from their approach?

Let’s break it down.

Master of Upsells

Imagine you’re a company looking to hire remote workers. You navigate to Remote OK, ready to post a job, and you’re greeted with this:

Right away, you’re introduced to a banner suggesting a bulk job bundle with discounts. This is the first upsell. It’s a smart first move, targeting companies hiring for multiple roles. Then, as you move to the “Design Your Job Post” section, things really get interesting:

Here, Remote OK presents you with an array of upsell options. Want to add your company logo? Highlight your post in yellow? Stick it to the top of the page for a day, a week, or even a month? They’ve got you covered. The sheer number of options might seem overwhelming, but there’s method to the madness.

Two clever tactics stand out in this upsell strategy. First, nearly every option includes a red rectangle showcasing how many more views your job post could get by purchasing that specific upsell. There is also the counters on the bottom which gets exponentially higher as you click more upsell options. This is a simple yet powerful motivator—it connects the upsells directly to tangible results.

Second, many of these upsells come preselected. This taps into a psychological principle known as “loss aversion.” People hate giving something up more than they enjoy gaining it, and unselecting these options feels like losing an advantage. To add to this, unselecting certain upsells triggers a pop-up window that warns you about what you’re missing. It’s a subtle but effective nudge to reconsider.

And then there’s the $500 upsell to customize your job post in your company’s colors. This might sound outrageous, especially since it’s free on many other platforms, but it’s a genius move. For larger companies, spending $500 is less about functionality and more about standing out. It’s a way to signal their importance and dominance in a crowded marketplace.

The Results

So, Remote OK uses a ton of upsells. But do they work? 

Absolutely. Take a look at Remote OK’s job board, and you’ll notice just how many companies have opted for the $500 color customization upsell. This is proof that their strategy resonates with their audience. Larger companies, especially, seem eager to pay extra to ensure their job posts get noticed.

What’s more, the founder of Remote OK, levelsio, shared a tweet after implementing these upsell changes.

The tweet highlights how the average price paid per job post skyrocketed, directly boosting revenue. This isn’t just about one-off purchases—it’s about increasing the Average Customer Value (ACV). By bundling so many tailored options into the job posting process, Remote OK ensures that each customer contributes more revenue without feeling nickel-and-dimed.

Should I?

Why This Works

• Expands Revenue Opportunities: A flat price caps revenue per customer. Upsells create multiple points where users can choose to spend more, significantly increasing the Average Customer Value (ACV) without requiring additional traffic or users.

• Psychologically Easier to Justify: Small incremental upgrades feel less intimidating than a single high flat fee. Spending $49 to highlight a post feels easier to justify than paying an additional $200 upfront, even if the total ends up higher.

• Customizes the Experience: Upsells allow each customer to tailor their purchase to their specific needs. Instead of forcing everyone into a one-size-fits-all pricing model, companies can choose the features that matter most to them, creating a more personalized experience.

• Encourages Competition and Exclusivity: The upsell model creates a dynamic where companies compete to stand out by investing in features like custom colors or banners. This wouldn’t work in a flat-price model, where everyone gets the same tools. Upsells allow companies to differentiate themselves, fostering exclusivity and signaling their commitment to attracting top talent.

How to Apply It

• Offer Upgrades That Solve Specific Problems: Design upsells that directly address your users’ pain points. For example, Remote OK’s highlighting feature targets companies worried about visibility. Think about the small but impactful improvements your users need, and make those your upsells.

• Tie Upgrades to Measurable Outcomes: Show users what they’ll gain. For instance, Remote OK includes a red box with view estimates for each upsell. This ties the cost of the upgrade to a tangible benefit, making it easier for users to justify the purchase.

• Leverage Loss Aversion: Pre-select valuable upgrades to nudge users into keeping them. Make sure the default options are genuinely useful so users feel they’re losing out if they uncheck them, rather than feeling pressured.

Yes, But

• Risk of Overcomplicating the Process: Offering too many upsells can overwhelm users and lead to decision fatigue. If the process feels cluttered or confusing, customers may abandon their purchase altogether, especially in industries where simplicity is key.

• Potential for "Upsell Paralysis”: Some customers might feel pressured to pay for extras they didn’t initially want, creating resentment or decision regret. This could lead to lower satisfaction or reduced repeat usage.

• Dependency on High-Tier Customers: Upsell-heavy strategies often lean on a small percentage of high-spending users. If these big players shift to competitors or experience budget cuts, it could disproportionately affect revenue.

Keep Learning

Others Playing It

Vistaprint, a popular online platform for custom printing services, excels at upselling by offering customers tailored options to enhance their products. For instance, when ordering business cards, customers can upgrade to thicker paper, premium paper stock, embossed gloss finishes, or rounded corners.

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Cheers,

Nico