How to Be a Great COO: Lessons Learned Leading a Unicorn to Success

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On Wednesday, February 17th at 9:30 AM PT, Redpoint Office Hours will host Allison Pickens, the former COO of Gainsight and one of Fortune’s Most Powerful Women. Throughout her time there, she scaled the SaaS company from $1M ARR to pre- IPO, along the way, creating the category of customer success software, and paving the way for Gainsight’s $1.1B sale. Today, she advises and invests in companies on these topics and others.

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A Common and Critical Mistake When Forecasting Next Year's Bookings

It’s February 1st and many software startups herald the new fiscal year with Sales Kick Off (SKO). During SKO, leaders discuss the strategy of the company, discuss product advances, and share the financial plan highlights including changes to quota and accelerators for sales commissions.

During the past few weeks, finance and management teams will have been busy developing the financial plan for this year. The key number is the new bookings which implies the growth rate for next year.

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The Five Flavors of ARR - New Definition, Same Great Multiple

There’s a trend in pitch decks and startup pitches I’ve been watching - the commingling of metrics definitions, especially ARR. Everyone reports ARR today, even in transactional businesses and market place businesses, and for good reason. The valuation multiples on annual recurring revenue are the highest across startup categories.

Ten years ago Startupland began to talk about valuing early and mid-stage startups on multiples. Today, it’s de rigeur and that’s not changing anytime soon. Management teams and VCs talk multiples in partner meeting presentations, term sheet negotiations, and board room conversations. Multiples are a useful yardstick to answer the question: how do these terms compare to others’ multiples, and so it is a fair deal or a great deal?

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The Secret to Keeping Your Software Running and Keeping Customers Happy

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How important is uptime to your business? As more business moves online, an increasing number of companies have to answer than critical question.

When products and services fail, customers can’t buy online or use their software, they churn, and the company suffers brand damage. Too much downtime can trigger clauses in software contracts for service level agreements (SLAs), which start cancellation conversations.

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Information as Surprise - Harness Claude Shannon's Key Idea

How do you measure how much information a statement contains? The short answer is surprise.

If you live in Los Angeles and I told you the weather tomorrow would be sunny, you would receive no information from me. It’s sunny there every day. But if I told you Salesforce intends to buy Uber to ferry salespeople to their prospects, that would be interesting!

Claude Shannon invented this idea, information as surprise. His theories enabled modern-day computing, with many others contributing. And if you’re curious about that chronology, read the sublime book The Dream Machine, but let’s stick with information as surprise for this post.

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Internal Communication - Why it Matters More than Ever & How to Succeed

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On Thursday, February 4th at 9:30 AM PT, Redpoint Office Hours will host Daria Kissner, who built and led internal and external communications for Google Ads and Commerce, and YouTube.

With the transition to remote work, the discipline of internal communications has become critical for startups to master. Keeping teams motivated, aligned, and connected when each person is in a different place is a new muscle for many startups to train.

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Cloud Data Lakes - The Keystone to the Decade of Data

On January 27-28, Dremio host their second Subsurface conference. Cloud Data Lakes are the future of large scale data analysis, and the more than 5000 registrants to the first conference substantiate this massive wave.

This time, the conference will build on the foundation from last year’s event.

Mai-Lan Tomsen Bukovec, Global Vice President for AWS Storage will deliver one of the keynotes. Also, Tableau’s Chief Product Officer François Ajenstat will discuss the Tableau’s role in the cloud data lake. Plus, leaders from Microsoft PowerBI, Apache Iceberg, Amundsen, Monte Carlo and many others will share their views on the advances they’re seeing in cloud data lakes and the software that’s being built around them.

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The Fastest Growing Sectors of Startup Fundraising in 2020

From time to time, I chart the fastest growing categories of startup investment in the US for seed through Series C. Here are 2015, 2017, This year, I was certain the categories would have been influenced by COVID19.

I analyzed Crunchbase data and looked for the startup categories that grew fastest in terms of funding rounds year-over-year, provided there were at least 10 rounds in that category.

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The Art of Doing Science & Engineering

The Art of Doing Science and Engineering is a curious book. Richard Hamming, the author, was a professor of science and engineering at the Naval Postgraduate School and researcher at Bell Labs. He knew quite a bit about science and engineering.

The book is curious because it’s written in the first person and defies categorization. Part memoir, other times, a mathematics lecture on information theory, and yet others a book on life philosophy.

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The Missing Insight Around Software Multiples for Valuing Companies

Imagine two public SaaS companies, identical in every respect but one. The first grows revenue twice as fast as the second. How much more valuable should the first be? Twice as valuable isn’t the answer.

Most investors value stocks using multiples, which tend to obscure the underlying drivers of value. Many investors also seek to distinguish between value and growth stocks, which are commonly sorted based on multiples of earnings or book value. The important drivers of value are opaque with these practices, and very few investors have a clear sense of how revisions in expectations for those drivers change multiples.

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