what SaaS startups can learn from Billie Eilish

Happy Friday friends! And congratulations on making it through another week. June is right around the corner and so is SaaStock Remote, where the theme this year is adapting, surviving, and thriving. We’re giving away 10 tickets to the playbook faithful, just use the code: THESAASPLAYBOOKCOMP when registering… It’s first come, first serve.

Alright, let’s dive into this week’s Playbook!


🎤 What can SaaS companies learn from an 18-year-old pop star? For one, creating an authentic and recognizable brand. Hear us out here. Billie Eilish amassed a following of over 50 million in just four years by breaking out of the cookie-cutter pop star mold and creating a persona that is unique and disruptive. Think of it in these terms: if your brand is simply adhering to the industry quo, what’s making your audience stop and pay attention? Nothing. Your brand identity needs to extend beyond basic design elements and focus on who you are as a whole. Focus on how you communicate and the style in which your company conveys messages to your audience. 

🛥️ We’re seeing more founders and CEOs hiring a Chief of Staff—they recognize that even the most talented multi-taskers can’t do it all if your number one priority is scaling. So to focus on what matters most, it’s paramount that your company’s ship has a first-mate. While there isn’t a universal definition for the role, the value of having one is that they’re able to fill the gaps that CEOs might miss, from project management to weeding out meetings deemed a time-suck. Something to keep in mind when looking for the right person to fill the role, don’t just think about the stereotypical candidate with exceptional organizational skills and look for someone who can really enhance your leadership style.

💼 Investor meetings can trigger anxiety even within the most confident founder, but you can start off on the right foot by sending a teaser beforehand. We like Mark Suster’s thoughts on what to send out before investor meetings, but the idea applies to board meetings as well. In both cases, you don’t want to give away too much info upfront and make your meeting seem useless, so if you’re pitching, create a teaser deck to get the group’s head in your idea and build excitement. If we’re talking board or shareholder meetings, create a similar overview of the items to cover and key details. That way they can gather their thoughts and even debate internally beforehand, otherwise, that might end up being your meeting! 


🥶The cold email. If you’re like us, you dread sending one almost as much as receiving one. After analyzing over 300K cold emails, Gong noticed that where most were missing the mark was in their CTA. When making initial contact with a prospect, most of us take great care to ensure we are relatable and sound human rather than an automated sales email. But after wading through the virtual niceties, we go straight into asking for a sales meeting. They suggest selling the conversation rather than focusing on a specific meeting time; ask your prospect if they’re interested in continuing the conversation, don’t assume. After all, a meeting is a time investment and we all know how valuable time is.


🛠We caught the latest episode of Blake Bartlett’s BUILD podcast where he talks to David Grow, President and COO at Lucidchart. They take a deep dive into Lucidchart’s shift towards a self-service business model and the resulting new customer journey. David explains why you should think of self-service as a fundamental part of your strategy as opposed to an operational tactic. There are some great bits on how each of his teams play a separate but crucial role in making the change come to life.

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