Hi, I'm a partner at Redpoint. I invest in Series A and B SaaS companies. I write daily, data-driven blog posts about key questions facing startups. I co-authored the book, Winning with Data. Join more than 18,000 others receiving these blog posts by email.

The Risk Sales Discounts Impose to Startup Burn Rates

Creating a sense of urgency is one of the most powerful sales tools available to SaaS companies. There are many different ways of accomplishing this, but one of the most common ways is to offer discounts that expire. Discounts are powerful incentives to increase sales. But, they have to be crafted correctly, or they can have dramatic impact on a startup's cash position. This is why sales incentives should be designed hand-in-hand with the company's finance team.

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Free SaaS Enabled Marketplaces - A Novel Go-To-Market for Software Startups

Traditional software was initially sold by perpetual license. Then in the mid-00s with the advent of SaaS, the market shifted to per seat per year pricing. And simultaneously, freemium marketing strategies blossomed. Freemium companies provide software for free temporarily to entice users to try and use the product. Eventually, these users cross a threshold and convert to a paid subscriber. This threshold can be based on number of people using the product (Expensify), number of documents signed in a month (HelloSign), or additional product features needed by users (Yammer). Today, we're seeing a new segment of the SaaS ecosystem move to free - the SaaS Enabled Marketplace (SEM).

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A Very Unusual Book about Startup Culture

Orbiting the Giant Hairball is one of the most unusual business books I've read. It's irreverent, full of drawings, and completely chaotic in the most wonderful way. Gordon MacKenzie, the author of the book, worked at Hallmark cards for 30 years to the day. He started initially in the creative department imagining greeting cards and ultimately found himself with the title Creative Paradox. In his book, he described the way he injected creativity into his working life. I thought it was a great book with three salient themes.

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The First Generation of the Talent Software Wars

In the late 1990s, two of the dominant talent management platforms were founded. Taleo and SuccessFactors grew very quickly after they entered the market, bringing novel delivery to the human capital market. Both companies eventually offered talent acquisition, performance management, and learning tools for human resources teams. But they started in different places. Taleo initially focused on recruiting tools and SuccessFactors on performance management.

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The 4 Teams Within Customer Success Organizations

At Gainsight's Pulse Conference on Customer Success, Mike McKee of Rapid7 spoke about the structure of his customer success team. He projected a slide, which I've copied in the image above, that depicts the way Rapid7 sells a contract, deploys its software, engenders adoption and expands accounts. It's the best visualization I've seen to describe the sales and customer success process and the inter-team collaboration required to be successful.

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From $800k to $274M in 4 Years - The Story of Ariba

Ariba went public in 1999 three years after having been founded. In its first year of selling, the company generated $800,000 in revenue. Then it ramped. $8 million, then $45 million, then $274M. In a three-year period, the company had grown 33x and achieved an astounding CAGR of 224% over the same period.

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The Optimal Compensation Plan for Customer Success Teams

At the Gainsight Pulse conference yesterday, I moderated a panel with Boaz Maor, VP of customer success at Mashery and Mike McKee, SVP of customer success and services at Rapid7. During the panel, both men described their path to building substantial customer success organizations at their respective companies. Boaz's team numbers 60 people, and Mike's exceeds 160. Over the course of the panel, we discussed the ways to recruit, structure, and manage vibrant customer success teams.

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The Decreasing Follow On Financing Success of Startups

The rate at which startups are raising follow-on rounds is decreasing, and has decreased steadily from 2003 through 2013. Between 2003 and 2006, post-Series A startups raised series Bs about 57% of the time. However from 2011-2014, that figure fell to 28%. The same trend is true in series C rounds, where success rates fell from 43% to 35%.

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The First Mobile-Only SaaS Company

Mobile visits account for more than 50% of all e-commerce]. During the holiday season in 2014, that figure exceeded 70% for Walmart. In India, mobile usage dominates traffic to such an extent that Myntra, the largest retailer, is shutting down their web application to focus exclusively on their mobile apps. Instagram launched a website only after the mobile app reached more than 100M users. If the consumer world is any indication of the future, we should expect to see a massively successful mobile-only SaaS company in the next few years.

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How Great Unit Economics Enables Startups to Weather the Storm - The Story of WebEx

In the late 90s, one company changed its name five times before they settled on one which today is a well-known brand. The business started as Silver Computing in 1995, then Stellar Computing in June 1997. Six months later, the company would rebrand as next ActiveTouch Systems, then six months later to ActiveTouch Inc., and finally, six months before IPO to WebEx.

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