The Four Types of Startup COOs

If you asked 5 people in Startupland to define the role of a COO, you would receive 10 different explanations. I have three myself. What does a modern COO do?

The role of a COO has evolved over the past decade or so because of broader changes within the ecosystem which has created some confusion what what precisely should a COO do. Recently, Redpoint Office Hours welcomed Allison Pickens to clarify the COO role and when startups should consider recruiting one.

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The Most Popular Startup Domain Suffixes - .com, .co, .gg - Which is Best for Your Business?

So you’re looking to start a company. What do you call it? Once you’ve figured that out, which domain suffix do you choose? .com, .net, .biz, .monster, .duck, .theworldisyouroyster? Given the explosion in domain suffix permutations I wondered if startups’ behavior had changed over the last decade.

In fact, it has changed significantly as the chart above shows. Click to enlarge the image.

Dotcoms dwarf other domain choices in demand but their dominance has diminished as the days pass. Down from 89% in 2007, the .com designation adorns the addresses of 64% of startups founded in 2020. Dotcoms are more dear because they are the default domain suffix most users type when dropping by a website. (alliteration)

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The Most Effective Tools and Techniques for Selling Today - Office Hours with Jim Benton

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On Wednesday, March 3rd at 10:00 AM PT, Redpoint Office Hours will host Jim Benton, CEO of Chorus.ai, a leader in conversational intelligence. As Co-Founder of ClearSlide and later as CEO of Apollo, Jim helped create the Sales Engagement category. From Evite to AdBrite to ClearSlide, Jim has expanded new categories and scaled revenue teams from zero to tens of millions in SaaS revenue.

2020 pushed sales teams to learn new sales motions selling online. Jim has been hosting weekly briefings with many top sales leaders exploring ways to navigate the turbulence. In addition, the Chorus team published the State of Conversation Intelligence Report which analyzed 35m sales calls to explore how the most effective teams sell today.

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How Much Should You Bet To Maximize Your Investments, or Your Company's Odds of Success?

If I gave you $1000 to invest, and five investment options how would you decide? What if you were the CEO of a startup, and a VC invested $10m, and each of your five VPs had different project ideas?

This is the question John Kelly, researcher at Bell Labs, sought to answer.

A contemporary of Claude Shannon, Kelly intertwined Shannon’s information theory with probability to develop an idea of his own: the Kelly criterion. His theory would translate into tremendous investing prowess and lead him to one of the best long term track records of all time at Princeton-Newport, a hedge fund he managed to 15% net IRR compared to the S&P at 8%.

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Eliminating Data Downtime with Data Observability - Why We Partnered with Monte Carlo Data

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At Redpoint, we believe 2020 is the decade of data. We’ve partnered in the leaders of the next generation of data from the earliest stages; companies like Snowflake, Looker, and Dremio.

Leaders rely more on data every day to inform our decisions, to power our products, and to communicate. In short, the data pipelines that move data from one place to another have become the nervous system of the modern organization.

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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.

Many businesses are moving their infrastructure and software to the cloud to adopt Kubernetes and microservices. Those technologies offer terrific benefits in exchange for some complexity.

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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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