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.

SMB or Enterprise - Which is the Better Go To Market in SaaS?

A friend recently asked, "Which path is better for SaaS startups? SMB to mid-market to enterprise or straight to enterprise?" It's a key strategic question for many founders building software companies.

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The Asset Allocator in Chief

A CEO uttered a brilliant statement in a board meeting recently. He said, "This experiment will cost $250,000 to run. After three months, we will know whether our new go-to-market strategy is viable." What's so clever about this statement? The CEO's frame of mind when marshaling the company's assets - time and money.

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Startup Best Practices 25 - Bounding the Unknown Unknowns

Every once in a while, I receive a FedEx from an entrepreneur I haven't met. Inevitably, this mail contains a modern rarity - a business plan. Ten to twenty pages describing the idea, the genesis, the business model, the team and its structure, customer acquisition strategy, sales model and other key details of the business. A plan for how to start a company, and a defense of the idea.

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Managing a User's Trust with Machine Learning SaaS Software

There's no quicker way to lose a user or buyer of your software than to lose their trust. The software didn't save my data. The database suffered corruption. The website is down frequently. Data integrity is a challenge every company storing data faces. Machine learning SaaS startups face another trust risk – one introduced by probability.

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Benchmarking Cloudera's S-1 - How 7 Key SaaS Metrics Stack Up

Cloudera is the second of the Hadoop players to go public. Last week, the company filed their S-1 and revealed a massive business. Cloudera generated $261M in revenue, counts 500 clients and grows those accounts by 43% annually. 18% of their customers run Cloudera software in the cloud.

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The Most Important Thing I've Learned about Writing

The most satisfying compliment the reader can pay this to tell me they feel personally addressed. Think of your favorite authors and see if that isn't precisely one of the things that engages you, and often at first without noticing it. A good conversation is the only human equivalent.

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Customer Operations - An Idea for Maximizing Efficient Growth in SaaS Companies

Over the last year in particular, Revenue Ops is a term that's gaining some mindshare in the SaaS world. Revenue operations teams combine marketing operations and sales operations into one team. Yesterday, I heard time a further refinement of this idea - Customer Operations.

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Creating Tension in Your Startup's Marketing Positioning

When I first met Jen Grant, Looker's CMO, she told me a story from early days of Box, where she was SVP of Marketing. Jen spoke about the importance of creating tension in the marketing message.

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When Should You Sell Your Startup?

When should you sell your business? There is no universal to this answer because the question is multifaceted and unique to each company. But we can answer another related question. Given a declining growth rate, when is my company's value maximized?

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Lies Managers Tell Themselves to Avoid Firing Someone

There are four lies managers tell themselves to avoid one of the hardest conversations in business. Things will improve. Someone in the seat is better than no one in the seat. Let's transfer the person to another team where things might improve. The termination will hurt morale in the company or the team. I've told myself all of these in the past. What's the best way to move past these and execute the difficult task of letting someone go?

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