Key Learnings from the SaaStr Annual 2019 Conference

Saastr Annual 2019: My Experience
March 6, 2019
Interview with Elena Shkarubo
March 20, 2019

The SaaStr Annual Conference, held in Silicon Valley, is one of the biggest names in the Cloud and SaaS ecosystem, and therefore of the most prolific tech conferences in the world. Today I will be sharing some key insights from the three day-long conference, providing you with a glimpse of what was discussed at the event “Where the Cloud Meets”.

The Five Questions CEOs Struggle With

It’s undeniable that CEOs have a lot to deal with; after all, it is their job to keep things running smoothly. SaaStr’s own former CEO spoke about the five questions he was always asking himself when he still had the job. These are worth thinking over and applying to your own venture.

  1. When do I next raise money?
    • You should seek investment in two-year cycles, in such a way that you may keep your operations running without the need for additional funding for two years. By raising money ahead of time in a stable schedule you can keep going without having to immediately scramble for funding, if something goes wrong,
  2. Do I have the right team?
    • This comes down to a matter of energy. If you have people who drain energy from your team, then you must get rid of them. If you have people who bring energy to the table, then you have the right team. Meetings should be something you look forward to, not dread.
  3. How can I better manage the board?
    • If the board members require a lot of input and micromanagement in order to function properly, then something needs to change. Set the board up so that they are productive and take care of the things you need them to.
  4. Should I worry about Competitors?
    • There are three perspectives you should consider: Competition, Vision, and Customer. Rather than being driven by one singular element, allow yourself to pursue all three in a simultaneous fashion. Speak of your Vision so that you may motivate people; cultivate a healthy Customer-centric culture in order to ensure that your people put them first; and finally outline Competitive goals and strategies, so that your company aims and works toward a big, successful goal.
  5. Are we focused enough?
    • The simple answer is no. There is always room for improvement, however small. In addition to this, keep in mind that having a vision does not equate to having a good strategy. Keep your vision in sight and construct a solid execution plan that will keep you focused.

IPO and Negative Churn

During the chat with Qualtrics’ former co-founder and CEO, he explained that Qualtrics started out with very limited external funding and bootstrapped for a long period of time. This in turn gave them a very strong position as they could grow organically without worries of external funding. He spoke of the benefits of going public and preparing your company’s IPO, as, according to him, that is the only way of truly controlling and influencing your company’s growth. While the risk of acquisition is real, it’s worth it. Also, another noteworthy concept was Negative Churn, that is, setting your customer base up so that referrals are generated. If you’re winning more business than you’re losing, then you’re in negative churn. This is the mechanism that allows you to build a self-sustaining machine that grows on its own without the need for you to do additional sales. This is how they sold Qualtrics for nine billion dollars with 45% equity.

Bessamer Venture’s Grid Score System

This session was mostly about the metrics through which you can keep track of your company’s well being and success, a grid score developed by Bessamer Ventures. The metrics are as follows:

  1. ARR: How much revenue you are annually recurring;
  2. Retention rate, which is market-dependant;
  3. Available funds;
  4. Targeted spend, that is, how efficient your finances are (measured with the net new ARR divided by the net burn).

These metrics, when combined, give you a sort of grid score that, along with your yearly growth, allow you to determine where you stand in terms of company quality.

Brex’s Henrique Dubugras on Self-Awareness

The young CEO underscored the importance of self-discovery. Find out what you’re great at, and then hire people to cover your weaknesses. Through this understanding, you can build a team that complements itself. This is the ultimate key to success; without a stable, dynamic team, success will be difficult to reach.

Key Points with Aaron Ross

Aaron Ross, co-author of From Impossible to Inevitable, spoke about the importance of doing interviews. Doing customer interviews allows you to really understand them, the market you’re working in, and helping you choose where to specialize and what to focus on. Ross also emphasized the importance of setting a Minimum Deal Size. If you are going to be making deals, they need to be worth it. Anything below the MDS should not be considered.

Michael Seibel on Learning from Failure

The main takeaway from this talk was Michael’s Top Ten Learnings from Failure, of which I will highlight a piece. Regarding hiring people, he said that if someone is not an essential employee after three months, then they probably aren’t right for the job and you made a wrong hire. Try to build a strong, essential team before expanding. Otherwise you will unbalance the team’s dynamic and hurt the company overall.

Capital: Bootstrap or Raise it?

Regarding this subject, it should be noted that bootstrapping is becoming increasingly more popular  among entrepreneurs and startups, so much so that it could become a trend in the future. In addition, I would like to point out that bootstrapping allows a safer development curve, protecting your company from the possibility of a crash, especially since if one does occur, and you are relying on outside investment, you may find that your funds dry up rather quickly.

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