Here's what worked and what didn't when marketing SaaS like Oh Dear

Where we're at in the scene

Oh Dear is the underdog in the website monitoring software space. We’re small fries in a market dominated by big, well-funded competitors. Yet somehow, Freek and Mattias managed to build a solid user base and created a profitable SaaS business. But where do you go from there? What was the eventual marketing strategy? We thought it would be cool to share with you guys our approach for Oh Dear, our lessons learned, and the strategies that helped us grow.

Started from the bottom, now we're here

After launching Oh Dear, the boys were able to get some solid traction going thanks to their personal network. Both Freek and Mattias are well-known in the Laravel community, each running their own successful businesses—the cron.weekly newsletter (Mattias) and Spatie (Freek). Their developer-focused blogs and community presence helped spread the word about Oh Dear organically.

Thanks to word-of-mouth and strong community engagement, we scaled to about 2,000 users without spending much on marketing.

But they knew they had to expand their audience beyond their own network. This is when Brandimpact entered the picture, a teeny tiny marketing agency from Ghent, Belgium, to help the boys start experimenting and build a robust, overarching marketing strategy. Below is an overview of what we did to better market Oh Dear throughout 2024.

Phase 1: Getting the ball rolling

The Brandimpact gang got work doing the following:

• Customer interviews to better understand Oh Dear's ideal users
• Competitor analysis & keyword research to refine our positioning
• A strategy workshop to set the priorities for the next six months

The goals? Increasing awareness, improving conversion rates, and exploring less obvious acquisition channels. Initially, we kept the personal networks of Freek and Mattias out of the picture, to see how independently the marketing efforts could run.

Since all of this was still very experimental, we limited our monthly media budget to approximately $5.000 per month for PPC (pay-per-click) advertising.

What worked

1. Google Search Ads (With Limitations)

Google Ads helped generate some free trial sign-ups, but at a pretty high acquisition cost. Since many competitors are obviously bidding on the same keywords (“website monitoring software”, “uptime monitoring software”), we were often outspent. While it brought in leads, it wasn’t sustainable for a bootstrapped SaaS like ours.

2. CRO (Conversion Rate Optimization)

We improved our website and trial experience by:

• Creating and adding a product video to the homepage
• Making our copy more engaging and clear for our target audience
• Extending the free trial from 7 to 30 days
• Collecting and adding more customer testimonials

Here's the video we ended up with, by the way. This was actually a lot of fun to do:

3. Reddit Ads — Better than expected

We didn’t expect much from Reddit Ads to be perfectly honest, but given our target audience we figured it was worth a shot. But as it turned out, Reddit ended up being one of the best-performing paid channels for us in terms of acquiring new trial sign-ups. We tested three different campaigns on Reddit:

• A feature-based carousel ad
• A product video featuring Mattias & Freek with a fun hook
• A series of memes using popular formats

Though we will say the quality of the traffic might be debatable—lots of clicks but not much else.

What didn’t work

1. LinkedIn ads – Too expensive

We targeted CTOs and developers, but the cost per click was too high. LinkedIn might work for enterprise SaaS, but for our niche, it wasn’t worth the investment.

2. Meta & YouTube ads – No significant impact

We briefly tested Facebook (Meta) Ads and YouTube Ads, but they didn’t generate enough quality leads. Developers don’t typically discover technical tools through these platforms.

3. Twitter ads – Garbage clicks

Arguably the worst advertising services among social media platforms. Lots of reach and clicks but absolutely abysmal quality. We're suspecting many among them were just bots.

Phase 2: Tuning our strategy

All in all, we were driving traffic but conversions weren't exactly growing in a similar fashion, so we turned our attention to re-activating our audience, leveraging SaaS aggregators and content marketing.

1. Affiliate marketing – Activating our user base

We already had an affiliate program offering 25% commission per sale, but few affiliates were actively promoting us. To improve this, we:

• Reached out to existing customers
• Created a press kit with ready-to-use content
• Updated the affiliate landing page on the website
• Optimized our affiliate onboarding emails

2. SaaS review platforms – Leveraging G2 & Capterra

Like most people, developers tend to trust their peers, so we focused on building a strong presence on platforms like G2 and Capterra. It's kind of an SEO effort as well, since these platforms work similary to Google in terms of ranking search results.

• We added review badges to our site
• We launched campaigns to encourage users to leave reviews
• We paid for a Capterra CPC campaign (~€40 per free trial)

Results? So far, Capterra (Gartner) has been our best-performing paid "channel" for free trial sign-ups.

3. SEO & content marketing – Playing the long game

We invested in SEO-driven content, but competing for high-intent keywords (like “uptime monitoring software”) remains tough. To improve our rankings, we're:

• Publishing SEO-optimized blog posts (see our blog)
• Focusing on getting backlinks from SaaS review sites
• Reaching out to tech blogs that review monitoring tools

Example outreach targets:

• Middleware.io's blog on website monitoring tools
• PCMag’s Best Website Monitoring Services

4. Direct outreach with gifting – Taking things offline

We’re currently planning a gifting campaign targeting digital agencies in Belgium. The idea is to send over a little care package—as in, a couple of Belgian beers—to a series of target accounts. Custom packaging, a personalized message, nothing too sales-y either. Freek and Mattias were actually at a bar drinking said beer when the idea for Oh Dear first came up, so it's a fun little tie-in to the product.

Final Thoughts: What We Learned About Marketing a SaaS

1. Personal networks & word-of-mouth are powerful, especially in the developer community.
2. Paid ads (safe for Reddit & Capterra) weren’t particularly effective.
3. SEO & review platforms can drive sustainable growth.
4. Don't be afraid to try something you're not familiar with. Trust is key, though.
5. There's no silver bullet, every audience is different.

Our marketing strategy is always evolving, and we’ll keep refining our approach as we learn. Keep you posted!