I'm a partner at Redpoint and write daily, data-driven blog posts about key questions facing startups including how to fund raise, startup benchmarks, management best practices and team building. I co-authored book, Winning with Data. Join more than ten thousand others receiving these blog posts daily by email.


Why Bottoms Up Selling is a Fundamental Shift in SaaS

Much has been written about the consumerization of IT, the movement fueling many SaaS startup's growth by targeting individuals in a target customer called B2C2B, rather than selling top down. But until yesterday, I hadn't found anyone who had quantified the size of the movement.

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Four Important Data Points about Purchasing Behavior in SaaS

The SaaS ecosystem has been evolving incredibly quickly. Most of the time, the changes in the ecosystem are embodied in one particular company which grows exceptionally quickly. Focusing on these fast-growers, the macro shifts can be hard to discern. Last week, Okta released a report Business at Work sweeps across SaaS to reveal these recent evolutions. These are the points that I found most interesting.

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What SaaS Startups Miss in User Onboarding

Over dinner, a veteran product manager argued most SaaS products' onboarding practices miss a crucial step: create value for the user in the first session. After that conversation, I signed up for many brand-name SaaS products pretending it was for the first time, and I couldn't help but agree with him.

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The Impact of the Stock Market on SaaS Valuations in 2015

The public markets are down more than 10% from their highs in the last few months. Public SaaS companies have been particularly hard hit. The chart above shows the enterprise value of publicly traded SaaS companies. Many of them are down substantially more than 10%. Let's dig in a bit more.

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Startup Trends from YCombinator's Demo Day

I've been to many YC Demo Days and I always look forward to them. This year was no exception. There are so many wonderful ideas and companies founded by terrific entrepreneurs. In addition to the pitches themselves, the types of companies presenting forbear trends in the startup world more broadly.

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The Number One Objection in the Sales Funnel

The most potent weapon in sales is understanding a buyer's perception of time. As Mark Roberge wrote, "At HubSpot, this lacking sense of urgency is the number one objection we face in the sales funnel." To succeed, SaaS startups' sales teams must consistently create urgency in the sales process.

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The 3 Ways Culture Enables Startups to Scale

While culture may seem an ambiguous and fuzzy concept, strong cultures are the best way for leaders to manage their companies throughout their evolution. One founder/CEO described his company's rapid growth to several hundred employees in just a few years this way. First, I was one of a few founders. As we grew, I became a manager of people. Then a manager of managers. And now I'm a manager of managers of managers. At this scale, CEOs can't be in every room opining on each choice, but they can influence how each decision in those rooms is made.

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Startup Best Practices 16 - Option Pool Planning

No matter the stage of the business, startups need to manage the size of their Employee Stock Option Pool or ESOP. The ESOP contains the shares set aside by the company for hiring and retaining employees. Like a financial budget, ESOP budgets help a startup plan how to finance its growth.

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The Magic of Email Snooze

In a recent First Round Review article, former Google President of Enterprise Apps Dave Girouard voiced the importance of speed in making decisions. "Deciding on when a decision will be made from the start is a profound, powerful change that will speed everything up." I believe this statement is broadly true, and no where else is it more tangible for me than in managing daily email. After all, what is responding to email other than a thousand decisions?

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The Implications of Raising a High-Priced Round

When we say a startup has raised a big round, we often mean the round is big in two dimensions - total amount invested and valuation. And when we say a big valuation, more precisely we imply the round was priced at a high revenue multiple. A SaaS company that will generate $400M in revenue next year that raises $200M at $1B valuation has raised a big round, but at low valuation-to-revenue multiple of 2.5x. In contrast, most high growth SaaS startups are raising at very high multiples, somewhere between 10-20x forward revenues. What are the implications of raising at a large multiple?

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