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.

How Zapier used FOMO to hit 50m ARR

Happy Friday folks! We’ve got bigger news than Joe Rogan’s Spotify deal—please welcome the newest member of the SaaS Playbook team, Bern! 

She’s a fellow SaaS enthusiast who will be helping curate our playbook content and help push some other initiatives we’re noodling on (more on that in the coming weeks). Excited to have her on board.


📧 When Alex Lieberman started The Morning Brew, he didn’t expect to build a $13m dollar newsletter. He didn’t even intend to start a business; he was just a student looking to keep up with financial news. But he recognized that industry publications were pretty dull and not designed for he and his peers, so he decided to create more relatable content himself. He went with a variety of grassroots tactics to get it off the ground, like asking for sign-ups at lectures he gave to increase word of mouth. Pretty interesting how Lieberman mostly relied on his own curiosity to create the newsletter—he admits he isn’t a writer or skilled content creator. He just identified a problem and was relentless in solving it; it’s that same the same type of ambition he looks for in hires. 

🐾 While we’re on email marketing, let’s look at the way Vero broke down the nuances of email KPIs. They point out that just looking at campaign centric data, like open rates, CTRs, and conversions on a campaign by campaign basis is helpful, but limited. To really get the full picture, you’ll want to couple those basic metrics with the context about how your audience interacts with your brand. For example, you shouldn’t assume a fresh email subscriber is new to your brand; they could have been quietly admiring your tweets for a while.

As Vero puts it, “Customers don’t interact with or think about your company as separate marketing channels or individual email campaigns. So why would you track email performance in such silos?”

🤝 By amassing over 2,000 integrations in just nine years, Zapier continues to be a quickly growing player in SaaS, hitting 50m ARR just a couple years back. What was their secret sauce? Zapier started with a handful of key integrations to create an MVP, then they played on a simple but powerful principle: FOMO. As more operators caught wind of Zapier, they wondered why their competitors had integrations, and they were left out. By building out a solid partnership strategy, Zapier was able to get partners to build the connectors and even promote them for them.


💵 The cycling in and out of customers is the bane of most SaaS company’s existence. While new customer acquisition is vital, retention is even more important because what’s a leaky bucket worth? The quick and easy way to measure is the appropriately named Quick Ratio. As Ben Murray (The SaaS CFO) explains, the SaaS Quick Ratio measures your directional growth, or to simplify even further, net gains vs. net losses of bookings or subscribers. It’s one of those metrics that most people know but few actually measure on a consistent basis, so here’s your friendly reminder that there’s no better number to give you the heartbeat of your business.


🦎 We tuned into the SaaS Podcast’s most recent episode which features Paul Joyce, founder and CEO of the dashboard tool Geckoboard. It’s an inspiring story, Paul decided to make the leap from his banking job into entrepreneurship and took 4 years to just decide on what idea he wanted to pursue. That led to a dashboards MVP launched on Hacker News which garnered him a couple hundred signups. It wasn’t a ton of traction, but enough to get the feedback needed to iterate and push forward. He ended up using his life’s savings to give his growing idea 5 months of runway, and it paid off—today they have 5,000 customers and are doing over 5m ARR.

sketching your roadmap into reality

Happy Friday, hope everyone had a great week! Some congrats are in order for these 3 SaaS companies that just reached 100m ARR, which made TechCrunch’s list hit the dirty 30 mark. 

Webinar platform ON24 was one of them who might be riding the pandemic wave to an extent, curious to hear if any of you have used or tested it. Another more familiar member of the group was Active Campaign, which can best be described as marketing automation, though we never loved the ambiguity of that term... Free SaaStock ticket to anyone who can actually give us a clear definition.

On to this week’s best practices.


🥒 There’s power in creating a story around your brand (see our thoughts on Donald Miller’s “Building a Storybrand” a couple issues back). DesignPickle took it to another level and sketched out a roadmap for success to quite literally build their growth story and communicate business goals to the team in a memorable way. Their two main goals were to increase ARPU while continuing to drive customer count upwards, and doing both in tandem to ensure they weren’t just extracting revenue from a flat or shrinking install base. We hear the results were good, so you might just see a SaaS Playbook roadmap to success soon...

✍️ We generally think of SEO as a long term marketing strategy – set it up now and you’ll start to see better results way down the line. Shane Barker used his own website as an SEO test subject to prove that there actually are some changes you can make that will increase organic traffic in the short term. The one which we all should start doing (if you haven’t already) is long-form content. It seems counterintuitive as our attention spans grow shorter, but through a series of content testing, Barker found that developing lengthier articles had the greatest impact on his rankings. He also found that a keyword density of 1-1.5% was the optimal amount to noticed by a search engine while not overdoing it.


🕰️ While much of the world has slowed over the past couple months, sales reps and anyone in a business development related role have trudged on. We liked these insights from David Priemer on how they can sell more by losing faster. The key ideas here to remember:

  • Limit time the spent on lost deals, cut your losses and move on to the next one

  • Hyper-focus efforts on highly engaged prospects, they are your best chance to close

  • Streamline your discovery process, Premier found that the deals they lost had a 3x higher discovery phase length than wins

Moral of the story: In a time where each sale matters, shifting your strategy slightly and cutting out the fat early on in the sales process can yield worthy results.


📜 Whether or not you know it, your company’s content doesn’t just come from your marketers. It’s any material that you share with your audience, from the product blogs the CS team publishes, to the email sales reps send, to the decks management assembles. So really, and as Ann Handley’s bestseller is titled, Everybody Writes, and should strive to improve their abilities! The book details her own strategy for content creation, including how those of us who are “adult-onset writers” can be better writing planners and in turn, produce better content. Highly suggest it as a way to get the whole team on board and excited to contribute.

gritty tactics that SaaS co’s can use to scale

COVID-19 related layoffs continue to surge and tech is one of the many industries that have been hit hard. A number of our companies are still looking to hire right now so if you or anyone you know is looking for a new opportunity and open to moving down south, give us a shout. There are a few open recs on this page and if none of those are a fit, we’re happy to sift through the network to see if anyone we know might be interested. 

Thanks, and enjoy the weekend!  


💎 Content has been getting lots of attention over the past weeks because it’s a low cost, high return strategy if done right, but our fixation on content seems to go in and out of fashion quite frequently. We stumbled upon a 1996 essay by Bill Gates discussing the role of content in the success of companies as the internet gains traction. He had a great point, but as shiny new channels like paid and social ads arose, they stole our attention. One new subset of content you know we’re bullish on is community content, which adds some flair to one of the oldest genres of marketing. Just look at the early success of UGC, where marketers are able to utilize organic content posted by their customers—it converts at a significantly higher rate and is even cheaper to produce because you’re not the one making it!

🤖 When David Cancel founded website chat software Drift, chat was already a crowded industry, making their meteoric growth all the more impressive. They claim their GTM centered on building “6-star content” (basically really good reads) is what spurred their growth. SEO tool SpyFu did an analysis of Drift’s content to see if that was, in fact, their secret sauce. They found that the Drift blog’s bounce rate was a ridiculously low 26% (the average is 41-55%), which is pretty solid proof their high keyword rankings led to engaged web visitors. Relatively self-centered topics like product, branded, and case study account for 36% of Drift’s most popular posts (pic below), so don’t think that all of your best work will be broad top-of-funnel content. 

🐙 Social scheduling tool MeetEdgar took a much different approach than a hyper-growth startup like Drift, starting as an agency and even moving to info courses before selling through a SaaS model. This case study looks at more granular tactics they used to grow over time, including the use of low commitment CTAs. Nearly all the CTAs you see on SaaS sites are “Start Your Free Trial” or “Book A Demo”—MeetEdgar instead asked web visitors if they wanted to double their traffic (because who doesn’t), and used “Get Your Invitation” as the call to action. While the process is probably the exact same as signing up for a free trial, it sounds less burdensome and led to an insane 10% conversion rate from web visitors. 

📈 Last week (and plenty of times before), we discussed the importance of tracking metrics during these unique times, and luckily there are a few platforms that are doing just that at an aggregate level. Hubspot recently released a cautious notice that they have seen some positive signs over the last week with more customers closing sales in the final week of April than they have since the middle of March. Some more high-level positive indicators they saw were increasing web traffic and higher email open rates. Of course, this doesn’t mean the effects of COVID-19 are over, but it is refreshing to see signs that a recovery will be possible.


The Origin of Brands approaches branding the same way Charles Darwin approached evolution, using the “Tree of Life” as a metaphor for itssubject’s evolution. Take computers for example. The first were mainframes but further down their “branches” we find newer categories like personal laptops and workstations, which were inspired by competition between brands fighting for survival. The book encourages marketers to diverge from branches on the tree rather than converge different categories into one. Directly competing with a dominant player in your space is unlikely to work—just look at the established brands who tried to take on IBM’s mainframes and failed. The winners were the ones who advanced the world of computing into new areas were able to own those new categories. 

who's up for a sales and marketing brainstorm?

We just grabbed our tickets for SaaStock Remote on June 10-11 so mark it on your calendar now! As always they have an awesome speaker lineup including some of the best in SaaS, and this time around there will be virtual networking and exhibition sessions to at least make it feel like you’re getting out of the house. 

You can use the discount code in the pic below for 20% off your tickets, hope to see you there!


🏠 Since our recent crisis, work from home rules have been more flexible than a sales rep’s discount at the end of month. Document search tool FYI dove into the data to see exactly how the trend has evolved—from 2016 to 2018, the number of job posts on LinkedIn mentioning “work flexibility” rose 78% and “flexible work” became a major consideration for over 75% of the workforce. Technical roles had already started to skew towards remote, so sales and marketing are the departments seeing the biggest increase in remote work as of late. FYI reported that 90% of employees who test remote work don’t want to go back to on site, a stat we’re assuming was taken pre-pandemic, because we can’t be the only ones itching to get back to the office.

💳 We finally had a chance to check out all of SaaStr’s talks from their virtual conference and thought Profitwell’s Patrick Campbell killed it with this 20 minute presentation. Given that growth is hard to come by during a pandemic, the focus was on retaining existing customers. Some good news shared was that while B2B SaaS has stopped growing at an aggregate level, it hasn’t started shrinking like B2C. He recommended looking at payment failures, which seem to take a backseat to active churn despite accounting for 30-40% of total churn. We were surprised to hear that 80% of customers don’t even know their payment failed—to make sure customers are aware, enable payment retries rather than sending a warning email. And if all else fails, consider offering a discount or deferral of payments to avoid losing them altogether.

🚦 It seems like every marketing email that lands in our inbox is telling us exactly how we will get through COVID-19. So we found it refreshing to read Coatue partner Caryn Marooney’s brainstorm ideas on how to conduct sales and marketing right now. She caveats that the list isn’t a playbook, which makes sense because no one has a playbook for something we’ve only dealt with for a couple months. Her suggestion to conduct micro experiments seems like a smart way to test ideas in an unstable environment, and goes hand in hand with another one of her suggestions: finding new ways to fill the funnel. Video could be a great choice here as YouTube viewership hours are skyrocketing.


😡 Commission structures vary by sector and business priority, but this list covers some essentials that are good to keep in mind when creating a new plan. This may sound obvious but it’s probably the most common thing people get wrong: make the plan simple and understandable. If you overcomplicate commissions, your reps might not understand them, and will end up disappointed when their take home isn’t what they thought it would be. The list also recommends higher sales commissions for annual plans versus monthly to reflect the higher revenue and stability they afford. And AE’s will hate to hear this, but we agree they shouldn’t be paid for renewals unless they’re owning the support activities (which typically the CS manager does).   


🎶 In What You Do Is Who You Are, Ben Horowitz covers the nuances in creating an awesome work culture, calling upon examples from Genghis Khan to Amazon. As the title suggests, the key to creating your culture is through the actions you take as a leader. Just writing out a few core values on your website isn’t what is going to influence your team—they need to see that you live and breathe them! Horowitz acknowledges that most company cultures will differ, but that the two virtues every good company should embody are loyalty and trust. That starts being upfront and transparent with your team, and being able to give them the bad news when it’s needed. If you don’t, tough situations will continue to get worse.

Loading more posts…