I'm a partner at Redpoint. I write daily, data-driven blog posts about key questions facing startups. I co-authored the book, Winning with Data. Join more than 20,000 others receiving these blog posts by email.

How to Decide With Speed and Conviction

A startup's competitive advantage is execution speed. That quickness stems from a CEO's ability to decide and this ability separates the great from the good. According to a recently published Harvard Business Review article, one of the four key behaviors distinguishing exceptional CEOs is deciding with speed and conviction.

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Monte Carlo Simulations of Inside and Outside Sales Teams in a SaaS Startup

Recently, a VP of sales told me about the way he views the dynamic between inside and outside sales when managing a sales team. Inside sales is the drumbeat, a highly predictable sales organization whose consistency enables outside sales to swing for the fences. I never heard it expressed quite this way, but I do think there's some truth to it. To prove it to myself, I ran a Monte Carlo simulation for hypothetical startup.

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Shopify S-1 Analysis - Smiling All the Way to $10B

Shopify is an exceptional business. There are not many software companies who can nearly quadruple their enterprise value in two years. But Shopify has grown from $2.7B in enterprise value to more than $10B. What are the metrics behind this behemoth?

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Decision-Making Auditing

How do you help someone when that person knows substantially more about the question than you do? This is one of the most fundamental and frequent questions in management. I came across it first as a product manager. Then as a manager of teams. And last as a board member. In each of these situations, have interacted with people who knew substantially more about their area of expertise.

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How Much Should A SaaS Startup Invest in Sales & Marketing?

How much should a SaaS startup invest in sales and marketing at different stages of the business? This is a very nuanced question, but benchmarks do provide some guidance for what is reasonable. Sales and marketing investment depends on many different factors including establishing product market fit, the business's sales model (inside, field, freemium), and not least, cash balance and fundraising capacity.

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Ownership - A Defining Trait of a Leader

One of the hardest things for me is to admit is when I'm wrong. It's hard first to admit it to myself. But harder yet is to admit the error to others. It could be my wife or my colleagues. Most challenging of all is owning the error in a public forum. But admitting mistakes is a key defining attribute of a leader. Owning the mistake accomplishes one critical thing. It builds trust, because it reinforces a fundamental characteristic of our humanity. We are all fallible.

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Should You Consider Emotional Intelligence When Hiring Your Startup's Team?

How important is hiring for emotional intelligence? EQ or EI was introduced in 1964 by Michael Beldoch and popularized by Daniel Goleman in 1995. I hear EQ uttered in nearly every job interview and evaluations, and assumed that high EQ correlated to higher job performance. But I read two articles recently that changed my perception of emotional intelligence.

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The Challenges of the Platform Go To Market

One of the most difficult go-to-market strategies for startups is platform. Platform go to markets mean selling software that can do many things, depending on the customer need. Selling a platform is challenging for five reasons.

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The Theory and Data Underpinning Sales Commission Plans

Every startup's sales commission plan is different. But it's key to understand the theory and the benchmark data that governs the creation of sales commission plans to create a good one for your business.

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Hiring for a Discipline You Know Little About

Your startup is growing. You suspect you have initial product market fit. Time to hire the first head of each department. Sales, marketing, customer success, engineering, product management. Some founders might have experience or exposure into one of these teams. But rarely do they understand every one well enough to hire the right department chief. How should you do it? I've observed three successful strategies.

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