The Top 20 SaaStr Posts of 2020

Some years politely knock on the door. 2020 kicked it in, dragged a standing desk into the living room, and told SaaS founders to figure it out before lunch. That is exactly why The Top 20 SaaStr Posts of 2020 still feels so relevant. These posts were not just popular blog entries tossed into the internet confetti cannon. They captured what software leaders, investors, operators, and slightly sleep-deprived founders were obsessing over in real time: cloud growth, fundraising, pricing, leadership hires, customer retention, the Bay Area debate, and the ever-glorious question of who actually makes more money in tech, founders or VCs.

What makes this roundup especially interesting is that it was published during a year when SaaS did not simply survive chaos; in many corners, it accelerated through it. While traditional IT spending faced pressure, cloud businesses kept grabbing budget, remote work changed software adoption almost overnight, and the best SaaS companies started to look less like scrappy software vendors and more like giant, category-defining machines with very expensive logos. In other words, 2020 was the year SaaS stopped asking for permission and started buying a bigger chair.

Below is a fresh, reader-friendly look at the 20 SaaStr posts that stood out in 2020, why people clicked them, and what they reveal about the state of SaaS at the time.

Why These SaaStr Posts Mattered in 2020

The 2020 SaaStr list was not random. It mirrored the exact pressure points SaaS leaders were dealing with. Founders wanted to know whether cloud demand would hold. Revenue teams needed better compensation design. Investors were rethinking risk, bridge rounds, and cold outreach. Operators were asking smarter hiring questions for sales, marketing, and customer success leaders. Even geography became a strategy debate, with the Bay Area suddenly looking less inevitable and more like an expensive group project.

At the same time, the macro backdrop was wild. Digital adoption accelerated at a speed that made even seasoned operators blink twice. Public cloud markets kept expanding. Some software companies posted eye-popping growth, while others signaled caution. That tension is what made the best SaaStr content resonate: it blended optimism with hard-earned operator realism. Not “rah-rah, everything is amazing,” but more like, “Yes, the market is huge, but please read the fine print before you hire the wrong VP.”

The Top 20 SaaStr Posts of 2020, Revisited

1. The Era of the SaaS Decacorn Is Here

This post captured the giant mood swing of 2020: from early panic to full-on amazement at how quickly elite cloud companies surged. The point was simple but powerful. SaaS had entered an era where billion-dollar outcomes were no longer rare trophies. Ten-billion-dollar cloud companies were becoming the new benchmark. It was part celebration, part warning shot: the ceiling for SaaS just moved.

2. How Would a Person Start a Venture Capital Fund?

Nothing says “healthy ecosystem” quite like operators suddenly wondering whether they should become investors. This post drew attention because it peeled back the curtain on venture capital. The glamour is obvious. The grind is less Instagrammable. For founders, it was a useful reminder that raising money and managing money are two very different sports, even if both involve spreadsheets and strong opinions.

3. Atlassian and AWS Say: Maybe Worry a Little Bit

One of the smartest entries on the list, this post balanced the sky-high optimism with a dose of realism. Even in a strong cloud market, leaders still needed to watch slowing segments, cautious guidance, and macro uncertainty. Translation: just because software is having a moment does not mean every dashboard should be covered in victory stickers.

4. A Framework for Your First SaaS Sales Comp Plan

This one remained popular because compensation plans are where strategy gets painfully real. Founders love talking about growth. Sales reps love being paid. A good comp plan is where those two dreams either shake hands or start a small fire. SaaStr’s appeal here was practical: operators needed formulas, not philosophy.

5. Additional Health & Safety Rules for 2020 SaaStr Annual

Yes, it is one of the most 2020 titles ever written. But it mattered because it documented the moment the industry realized in-person playbooks were broken. The post reflected a broader shift from physical conferences to digital events, and from “let’s wait this out” to “we need a new operating model now.”

6. What Makes a Great VP of Sales and How to Hire One

This stayed popular because nearly every scaling SaaS company eventually learns the same lesson: hiring a VP of Sales is not a trophy move. It is a high-risk, high-leverage decision. Great sales leaders match stage, motion, and market. The wrong one brings fancy slides, inspirational adjectives, and a fast route to regret.

7. VCs or Founders: Who Makes More?

This post scratched a timeless itch. Everyone wants to know where the economic upside really lands. The answer, unsurprisingly, is nuanced. A top founder can create generational wealth. A top venture capitalist can compound wins across multiple companies. The fun part is watching both camps pretend they are mostly doing it for the love of the craft.

8. 2 Cold Emails I Funded for Millions

Founders adore proof that a cold email can work, because it means the castle gates are not fully locked. This post resonated because it offered real examples and reinforced a simple truth: a crisp, credible, well-targeted pitch can outperform a warm intro wrapped in fluff.

9. What Are Typical Price Increases in SaaS?

Pricing gets less hype than fundraising, but it quietly determines whether a company builds a good business or just a busy one. This post hit a nerve because SaaS pricing is one of those topics people love to underthink until renewal season arrives carrying consequences.

10. Public SaaS Companies Are Now Worth $1 Trillion

There are milestone numbers, and then there are numbers that make the whole market sit up straighter. Crossing the trillion-dollar threshold helped confirm that SaaS was no longer a niche category. It had become central to modern business infrastructure.

11. About 70% of SaaS Unicorns Are New Versions of Existing Categories of Software

This may be the most comforting and irritating lesson on the list. Comforting, because founders do not always need to invent a totally new category. Irritating, because execution matters so much more than novelty. The world rarely asks for “something never seen before.” It often rewards “something much better than the current headache.”

12. At the Top SaaS Companies, Founder-CEOs Own About 15% at IPO. And Most Co-Founders Are Not Equal

This one landed because cap tables fascinate people the way true-crime podcasts fascinate suburban commuters. Everyone wants the details. The post cut through startup mythology and made a practical point: equity outcomes are not equal, and pretending otherwise does not make the spreadsheet more democratic.

13. The Covid Boost for SaaS Will Last Years

In hindsight, this post was less a hot take and more a preview. It argued that the pandemic-driven shift toward software would not vanish the moment offices reopened. The stronger insight was that behavior changes create budget changes, and budget changes tend to linger.

14. How Bridge Rounds Work in Venture Capital: Messy, Full of Drama, and Not Without High Risk

Bridge rounds sound harmless, like a polite little bridge over a calm little stream. In practice, they can be full of dilution, signaling issues, and enough awkward investor conversations to make anyone suddenly interested in bootstrapping. This post did well because founders wanted candor, not sugar glaze.

15. Should Google Acquire Salesforce?

Part strategy exercise, part software fan fiction, this post tapped into a larger question: how much bigger can the enterprise software chessboard get? Even if the hypothetical never became reality, the discussion reflected how central SaaS leaders had become to platform power and market structure.

16. 9 Questions to Ask Candidates for Your First Head of Customer Success

Customer Success earned its seat at the main table years ago, but 2020 made retention and expansion even more valuable. This post was popular because founders were finally treating customer success as a revenue and retention function, not just a nice department full of earnest people with Zoom fatigue.

17. Is This the Beginning of the End of the Bay Area as the Global HQ of SaaS?

Ah yes, the great relocation debate. This post captured a moment when distributed work suddenly made geography look negotiable. The Bay Area did not collapse into fog and artisanal toast crumbs, but the post raised an important point: talent, culture, and access were being re-priced in real time.

18. Grow Something That Matters. Even If It Isn’t Revenue

One of the most human posts on the list, this piece reminded founders that not every quarter can be reduced to ARR worship. In hard seasons, the right thing to grow might be customer trust, team stability, product love, or retention quality. Revenue matters. It is not the only signal that matters.

19. Don’t Leave the Bay Area Just Yet

And here came the counterargument. If post No. 17 was the breakup text, this post was the “maybe we should still talk” message. The takeaway was balanced: remote work changes a lot, but ecosystems still matter. Dense networks, operator talent, and startup serendipity do not disappear overnight.

20. Hire the Right Type of VP Marketing Or You’ll Just End Up With a Bunch of Blue Pens with Your Logo on Them

A title this good deserves to trend on personality alone, but the content also hit home. Marketing leadership in SaaS is deeply stage-specific. Brand marketers, demand gen leaders, and product marketers are not interchangeable action figures. Hire the wrong profile, and yes, you may end up with branded pens and zero pipeline.

The Bigger Themes Hidden Inside the List

1. 2020 was the year SaaS looked both unstoppable and fragile

That tension runs through the entire roundup. On one hand, cloud demand accelerated, digital adoption jumped forward, and top companies posted monster growth. On the other hand, leaders still worried about guidance, churn risk, field sales disruption, and how long the boost would last. This mix of confidence and caution is exactly what made 2020 such a defining SaaS year.

2. Hiring remained one of the hardest scaling problems

Three of the top posts focused directly on leadership hires: VP of Sales, Head of Customer Success, and VP Marketing. That is not an accident. Once a SaaS company finds product-market fit, execution quality starts to depend heavily on whether the first few executives actually fit the stage. Founders often want a hero. What they really need is a match.

3. Revenue quality beat vanity metrics

Pricing, expansion, renewals, retention, and compensation plans all appear across the list because mature SaaS thinking is less about “Can we grow?” and more about “Can we grow efficiently, predictably, and for a long time?” That is operator brain, and SaaStr readers have plenty of it.

4. Venture became more operational

Posts about starting a fund, cold emailing investors, bridge rounds, and founder equity all reflect a sharper interest in venture mechanics. Founders were not just looking for money; they were trying to understand incentives, ownership, and the real cost of capital. Very healthy. Slightly less romantic. Much better for the spreadsheet.

What Founders and Operators Can Still Learn from the Top 20

The best way to read this 2020 list today is not as nostalgia, but as a field manual. The specific numbers have changed. The software market has evolved. AI has barged into every conversation like an intern with a flamethrower. But the core lessons remain stubbornly useful.

First, category expansion rewards execution. You do not need a magical new market if you can build a sharper, faster, more lovable version of an existing one. Second, the first executives you hire shape your growth curve more than almost any dashboard metric. Third, pricing and retention deserve just as much strategic attention as acquisition. Fourth, fundraising is not just about getting a yes; it is about understanding what that yes costs over time.

Most importantly, 2020 showed that great SaaS companies adapt faster than their circumstances. They do not wait for certainty. They build through it. Sometimes elegantly. Sometimes while holding coffee in one hand and a half-finished forecast in the other.

Experience Section: What It Feels Like to Revisit the Top 20 SaaStr Posts of 2020

Revisiting The Top 20 SaaStr Posts of 2020 feels a bit like opening an old playbook and realizing half the pages are still useful, while the other half are now highlighted, dog-eared, and covered in mental sticky notes. The immediate feeling is not nostalgia. It is recognition. You can almost see why operators gravitated to these posts in real time. They were not reading for entertainment alone. They were reading because the market had gone off-script, and they needed answers that were practical enough to use before the next leadership meeting.

One experience that stands out when reading through the list is how deeply operational the curiosity was. Founders were not just asking big-picture questions like whether SaaS would keep growing. They were asking survival-and-scale questions. How do I pay sales correctly? Who should I hire first? What should I ask a Head of Customer Success candidate? How much should pricing increase at renewal? Those are the kinds of questions people ask when the company is real, payroll is real, and the consequences of guessing wrong are very real indeed.

Another striking experience is the emotional whiplash embedded in the list. Some posts celebrate gigantic outcomes and historic valuations. Others warn about bridge-round drama, executive mis-hires, and the need to worry “a little bit.” That combination is exactly what many SaaS teams experienced in 2020. One week felt like acceleration; the next felt like triage. One metric looked amazing; another looked suspiciously like a trap wearing a nice suit.

There is also something refreshing about how unpretentious the best SaaStr content can be. Even when the subject is massive wealth creation or billion-dollar categories, the voice often stays grounded in operator reality. The lessons are rarely framed as abstract theory. They are framed as decisions someone actually has to make, probably on too little sleep, with too much responsibility, and maybe a Slack channel on fire in the background.

Perhaps the most useful experience of revisiting this roundup is realizing how many “2020-only” debates turned out to be long-term questions. Geography. Pricing power. Customer expansion. Founder ownership. Executive hiring. Market timing. These were not temporary panic topics. They were structural SaaS questions that just became impossible to ignore during a chaotic year.

That is why this roundup still works. It captures a moment, yes, but it also captures a mindset: practical, curious, resilient, and just skeptical enough to keep the celebration from becoming delusion. And frankly, that mindset ages much better than most hot takes on the internet.

Conclusion

The top SaaStr posts of 2020 were not merely a popularity contest. They were a snapshot of what software leaders needed most during one of the strangest business years in recent memory. The posts that won attention were the ones that explained scale, hiring, pricing, fundraising, and market shifts in language operators could actually use. That is why they still matter.

If there is one final lesson from this list, it is that SaaS grows best when ambition and discipline travel together. Dream big enough to believe in decacorns. Stay practical enough to build the right comp plan, ask the right interview questions, and avoid the wrong bridge round. In SaaS, the headlines are flashy. The fundamentals are what keep the lights on.

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