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SaaStr Annual at Home: 10 Quick Takeaways

Todd Gibby
Sep 4 · 6 min read

As a card-carrying introvert, I’ve always found industry conferences to be exhausting. Likewise, over recent months, Zoom Fatigue consistently crushes me by mid-day Friday. So, I figured that a pandemic-induced remote conference would be some kind of “snakes on a plane” hybrid, uniquely designed for my personal torture. But, having just concluded my first honest-to-goodness attendance of a multi-day virtual trade conference, I am pleased to report that I was totally wrong. Rather, the SaaStr Annual at Home conference this week was engaging, informative, and — I can’t believe I’m writing this — energizing. Having been freed from the relentless distractions and demands of in-person conferences (networking, generating leads, striving to optimize investment in Travel & Entertainment), I paid much closer attention to the valuable content sessions than I normally would. I also appreciated moments of respite throughout the day which offered the opportunity to sense-make across sessions. The net result was a solid set of takeaways for a fraction the time / effort (and $); and I thought I’d share an eclectic mix of conference tidbits below.

1) “ARR is a fact, churn is an opinion:” This was a gem from one of my favorite sessions led by Dave Kellogg, who offered a fast-paced “how-to” of useful SaaS metrics. The specific point here is that churn can be defined and manipulated in many ways (true!), with collateral damage to the integrity of other metrics (also true). The broader point, which he supported with compelling data — focus on what matters to value-creation in the business. Roger that. (Session: “Churn is Dead. Long live Net Dollar Retention with Dave Kellogg”).

2) Remaining Performance Obligation (RPO) Intro: As a quick-and-dirty definition, RPO can be thought of as deferred revenue plus backlog. The Motley Fool offers a deeper explanation here, in connection to Splunk. This item came from the same “Churn is dead” session, which was the first time I’ve heard RPO referenced in connection to private companies. Makes total sense, and I’m eager to think about this more in the context of usage-based business models. (Session: “Churn is dead. Long live Net Dollar Retention Rate with Dave Kellogg”).

3) Managing Complex Change: Arquay Harris of Slack led one of my favorite sessions, and not just because she threw out the term Kobayashi Maru in her talk (her content was valuable and preso style was super-engaging). She referenced Sylvia Duckworth (the introduction to whose work alone was worth the price of admission) and shared the deceptively powerful graphic below which captures elements of managing complex change.

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I’ve written here about principles of leading change, but I think this graphic captures these concepts in an amazingly clear, concise, and digestible way. There is a 100% chance I’ll be re-using this visual down the line. (Session: “The Secrets of Managing in All Directions with Slack”).

4) Committee Buying: It’s not our imagination, there is much more buying-by-committee mid-pandemic among enterprises who are increasingly risk-averse, cost-conscious, and looking to consolidate their technology investments. Lots of work to be done around understanding more / new buyer personas and how to sell into a flatter organization where any single person has veto power. (Session: “Buying Patterns in the Enterprise: Who’s Really Buying & Why in a Post-Covid World with G2”)

5) Privacy Debt: Bessemer Venture Partners shared six predictions around the 2020 State of the Cloud (janky photo below):

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Why Can’t I Get PrScr to Work When I Need It?

The one that really resonated with me was: “Privacy debt will be the new tech debt.” In short, SaaS players that have not been making consistent, diligent investment in their solutions’ privacy envelope will undoubtedly face a reckoning where significant, costly catch-up on this front will be unavoidable. I suspect tech debt will continue to be a problem for many companies, so I’d maybe argue that privacy debt is yet another straw on the camel named “Tech Debt.” (Session: “State of the Cloud 2020: The COVID Beneficiaries Edition with Bessemer Venture Partners”).

6) Fun Still Matters: Ben Chestnut, founder and CEO of marketing platform giant Mailchimp, shared a great story of the moment when his development team transitioned from being mercenaries (less-productive clock-watchers) to missionaries (self-motivated true believers). It was when they started programming Easter Eggs into the solution. The point? Having fun is incredibly powerful in terms of culture, talent retention, brand, and so much more. True that — awesome interview. (Session: “Learning from the Lows: How Mailchimp Navigated Economic Uncertainty”).

7) Vertical SaaS Rules (Part 1): There were a number of sessions that focused on issues relating to vertical-specific SaaS businesses. We are big fans of vertical SaaS at Lock 8, so I enjoyed these immensely. Damola Ogundipe talked about how being a vertical SaaS solution gives Civic Eagle a leg-up in recruiting because it is easier to identify for culture and passion (and not just talent) relative to horizontal players. (Session: “Underserved Markets for SaaS Companies with Backstage Capital, Avisare, and Civic Eagle”).

8) Vertical SaaS Rules (Part 2): Songe Laron, CEO and Co-Founder of Squire made a compelling argument for why vertical SaaS solutions have an inherent advantage over their horizontal peers in terms of increasing average revenue per unit (ARPU) within their focused customer base. That same session underscored the corresponding point that market sizes for vertical SaaS players were often a whole lot bigger than they first appear…and that domain expertise in that market enables savvy operators to unlock TAM that remains hidden to the casual observer. Exactly! (Session: “Vertical SaaS 2.0: How Barbershops Are Creating a SaaS Rocketship with CRV and Squire”).

9) D&I — Early but Mighty: The topic of diversity and inclusion was understated, but never far from center-stage at this conference; and it came up in various organic ways throughout many sessions. I also attended one session where it was the explicit focus (“Which D&I Initiatives Really Work: The metrics you should be tracking with Notion Capital”). That session crystallized a shared conviction that advancing D&I in SaaS businesses is not only the right thing to do, but that it is also highly correlated with value creation…even as we are still early-on in the collection of supporting empirical evidence. In sum, I sensed that (a) this will be a major focus for SaaS businesses that acknowledge there is much to be done, (b) there is early demonstrable progress being made, (c) it doesn’t appear that anyone has all the answers, and / but we are feeling our way together.

10) “On” and “In the Business” versus “Out”: There is a well-known distinction between “working on your business” versus “working in your business.” What I have sometimes found off-putting about software conferences is the seemingly obsessive focus on “working out of your business.” By that I mean placing overwhelming emphasis on exits, liquidity, and valuation. Don’t get me wrong, those things are extremely important; but they can also suck all the oxygen out of the room. In this crazy, tragic COVID reality we are living through, I found that NOT to be the case at this event. Rather, I found that people were very much focused on “working on their businesses;” and it was really refreshing.

And…1 to Grow On (Humble Pie is Comfort Food): Similar to the point above, there can be a lot of posturing that occurs at SaaS conferences, and this tends to escalate in direct correlation with SaaS company valuations. Although SaaS multiples remain durable, the past six months have been enough to inject a bit of humility into all of us. This seemed evident in most sessions, where I perceived a genuine air of people wanting to support one another and offer humble assistance where possible. It created a comfortable environment for a conference; I certainly hope this aspect of our current environment has some staying power.

Made Not Found

Todd Gibby

Written by

SaaS operator-turned-investor | Founder of Lock 8 Partners | Sharing observations, thoughts, and lessons learned from the ever-educational journey.

Made Not Found

In SaaS businesses, operating results are earned every single day; and good businesses are made, not found. Writing here about building organizations, learning from the experience, and appreciating the ride.

Todd Gibby

Written by

SaaS operator-turned-investor | Founder of Lock 8 Partners | Sharing observations, thoughts, and lessons learned from the ever-educational journey.

Made Not Found

In SaaS businesses, operating results are earned every single day; and good businesses are made, not found. Writing here about building organizations, learning from the experience, and appreciating the ride.

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