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Data privacy has become a skill startups must master as they scale. As they grow, startups often collect increasing volumes of data. With great power comes great responsibility. Regulatory regimes demand greater data security and integrity, and add complexity.

How should companies manage data privacy, especially regulations like GDPR and CCPA? To answer that question, Redpoint Office Hours will host Todd Smithline on Wednesday, April 21 at 9AM PT. Todd is managing prinicipal of Smithline, PC, a San Francisco law firm focusing on technology transactions, product legal review, and open source advisory work. He has taught the video game law class at UC Berkeley School of Law since 2021.

More than a year after Covid washed over the software ecosystem and the tide ebbs, it’s revealing the impacts on fundamental metrics of public software companies. Sales efficiency is one of those key metrics. Covid altered the way salespeople and marketers engaged their target markets. Travel collapsed, virtual events blossomed, handshakes became Zoom namastes. How did sales efficiency evolve?

Across public software companies, the average sales efficiency fell from 0.6 to 0.51 over the last 3 years. The majority of that fall occured before Covid in 2019. In contrast, sales efficiency improved throughout 2020.

Would you work for this person?

It’s a simple question. It’s one I often ask in reference calls on founding teams. During one of those calls, when I should have been paying attention to the answer, I posed my self a similar question. What is it about a person that would make me leap to work for them?

Intellect, ethics, ambition, conviviality, mastery, ethusiasm come to mind. But, those are subordinate characteristics. What’s the one thing?

Open source software marries the decentralized community of the Internet with the ambition to build great things. Databases, application servers, streaming technologies, application deployment, and container management - many modern tools were born open source. But the clouds are rolling in for open source companies (pun intended). Today, open source software faces an identity crisis: what does it mean to be an open source company in the cloud?

Imagine you’ve co-authored a massively successful open source project and you’re on the cusp of commercializing it. You face a critical decision. This decision will impact the business for the next 24 months and beyond. It will determine your price point, your roadmap, your hiring plan, your revenue, and consequently your fundraising prospects. The decision reversible, but not without pain and difficulty, and likely 3 to 4 quarters of work. What is that decision?

UIPath, leaders in the Robotic Process Automation (RPA) category, filed their S-1 last week, revealing an impressive business. Founded in 2005 in Bucharest, Romania, by Daniel Dines and Marius Tirca, the company now operates more than 60 offices housing nearly 3000 employees.

UIPath offers software to build robots, programs that automate repetitive work. Some examples include streamlining customer onboarding. Robots read pdfs that customers provide and input that data into other computer systems. Customer support teams might use RPA robots to read the contents of an email, find an order number, look up the order, and present the support agent with some key data.

Developer tools and business-to-developer companies are among some of our favorite category of startup. We’ve had the privilege to partner with many of the leaders like Stripe, Twilio, Hashicorp, LaunchDarkly, SourceGraph, and Heroku, among many others.

Developer documentation is one of the differentiators in developer community building efforts. If you’re an engineer, and you hear about an interesting project, the first place you’ll land is the documentation. Guides that are easy to follow, have clear examples, and guide an engineer through a smooth experience grease the user engagement and acquisition funnel.

Recently, Jim Benton joined us for Redpoint Office Hours to share insights from his vantage point as CEO of Chorus.ai on how sales has changed during the COVID era.

Jim shared many data points that opened up my eyes to some of the challenges and the opportunities before modern sales professionals. I took away three key ideas, though we covered much more in the session.

I’ve been following many public market investors on Twitter over the past few weeks to understand how they view the vacillation of the public markets. One of the tweets linked to a speech Stanley Druckenmiller gave in 2015 about Black Wednesday.

At the time, Druckenmiller worked for George Soros at a hedge fund.

“George, I’m going to sell $5.5 billion worth of British pounds tonight and buy deutsche marks. Here’s why I’m going to do it, that means we’ll have 100% of the fund in this one trade”.

A 20% delta in net dollar retention (NDR) may not seem like much, just a trifle, but make no mistake, it’s massive. In preparing for a presentation at next week’s Saastr Build conference, I reviewed this S-1 analysis for DataDog that I had published a few years ago.

It shows the difference in the net dollar retention across three competitors in the same space, Application Performance Monitoring: DataDog, New Relic, and AppDynamics.

About a year ago, I wrote a post on the hub and spoke data model. The idea is that in the future SaaS applications would be built on a single database, instead of each SaaS application writing to its own proprietary database.

I was wrong about the catalyst for this hub-and-spoke model. I thought it would be cloud-prem and customers driving SaaS products to use a single database. Instead, the SaaS ecosystem and the data ecosystem are moving in this direction on their own.