From a Single LinkedIn Post to $2M ARR: The Unconventional Marketing Playbook of Massive

From a Single LinkedIn Post to $2M ARR: The Unconventional Marketing Playbook of Massive

Aug 6, 2025

The Genesis: A Serendipitous Spark on LinkedIn

The story of Massive doesn't begin in a boardroom with spreadsheets and market research. Instead, it started with a casual suggestion from an engineer on Dan's team: "What if we used GPT to automate filling out job applications?" While Dan was initially hesitant, he decided to test the waters by sharing the idea on LinkedIn. The result was nothing short of phenomenal. The post went viral, garnering an astonishing 8 million impressions and 5,000 comments. This overwhelming response was the market validation he needed, a clear signal that he had stumbled upon a significant pain point for job seekers.

The Waitlist Fallacy: A Lesson in Early Monetization

Riding the high of their newfound viral fame, Massive quickly built a waitlist. Within two short months, they had amassed an impressive 40,000 to 50,000 signups. On the surface, this looked like a massive success. However, the conversion rate from the waitlist to paid subscriptions was a sobering 0.5%. This experience led Dan to a crucial realization: waitlists can be a vanity metric, a "useless" indicator of true customer commitment. He now passionately advocates for charging customers from day one, even for a minimal viable product (MVP), as it provides invaluable data and a much clearer picture of your product's market fit.

Read a case study on the pros and cons of waitlists for startups

The Growth Engine: A Trifecta of Modern Marketing

Massive's current growth strategy is a powerful trifecta of paid advertising, user-generated content (UGC), and strategic influencer marketing. Dan's approach is all about rapid experimentation and iteration. He advises fellow founders to test their ideas quickly with a clear and compelling value proposition, rather than getting bogged down in endless cycles of content creation.

Cracking the Code: Content, Audience, and Conversion

Dan's insights into content and audience targeting are particularly illuminating:

  • The Power of Simplicity: In a world saturated with complex marketing messages, simplicity cuts through the noise. Massive's tagline, "Tinder for jobs," was a stroke of genius. It's a simple, relatable, and instantly understandable concept that resonates with their target audience.


  • The Art of the Problem Solution Skit: For Massive, problem-solution skits have proven to be a highly effective format. However, the key to their success lies in precisely targeting the right audience with the right problem.


  • Audience Nuance is Non Negotiable: One of the most critical lessons Massive learned is that not all audiences are created equal. Content aimed at white-collar professionals on LinkedIn resulted in high conversion rates. In contrast, content that went viral among a blue-collar audience on Indeed, while generating millions of views, led to low conversions and negative feedback.


  • The First Few Seconds are Everything: In the fast paced world of social media, you have a fleeting moment to capture your audience's attention. By directly addressing their characteristics and pain points within the first few seconds of a video, you can create an instant connection and stop them from scrolling.

Scaling Pains: Navigating the Challenges of Growth

The journey from a viral post to a multi-million dollar company is not without its challenges. Massive's experience with an 11 million view video that yielded minimal conversions is a stark reminder that views do not always equal conversions. Attracting the wrong audience can be a costly mistake.

Furthermore, while UGC has been a valuable part of their marketing mix, Dan admits that it's a challenging strategy to scale effectively. The intensive management required to consistently produce high converting content can be a significant bottleneck. In contrast, paid advertising offers more reliable data for iteration and scalability.

A Stand for Ethical Marketing

In an industry that is sometimes plagued by "grey hat" and "black hat" tactics, Dan takes a firm stand on ethical marketing. He unequivocally condemns misleading practices such as faking job acceptance videos or manipulating comments, emphasizing that such tactics are not only unethical but also illegal and ultimately detrimental to the industry's reputation.

Dan's parting words for Founders:

Dan's philosophy is a refreshing blend of ambition and pragmatism. He encourages founders to think bigger, to move beyond the "indie hacker" mindset and aim for significant, scalable growth. He believes that a genuine passion for your product and a deep understanding of your users are the most powerful marketing tools at your disposal.

Ultimately, Dan's success with Massive is a testament to the power of relentless execution and a willingness to learn from failure. He attributes the company's revenue growth not to a single magic bullet, but to a series of pricing changes and specific ad strategies that were discovered through persistent experimentation.

Ready to revolutionize your job search?

You can watch the full with Dan here.

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