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. Join thousands of others receiving these blog posts daily by email.

Trends In Startup Acquisition Market in 2015

This time last year, I analyzed the state of the startup acquisition market. Two key trends surfaced. First, the larger acquisitions were becoming larger. Second, that the total number of acquisitions in 2014 would achieve a 5 year high. As of mid-2015, the first trend continues while the second seems to have faltered.

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Three Data Points on Email List Unsubscribe Patterns

Ultimately, the goal of most content marketing campaigns is email address capture. When a reader decides to receive content consistently via email, a content marketer knows they're developing a deeper relationship with that person. Whether the marketers selling software or venture capital, retaining an email address is a victory.

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Startup Best Practices 14 - Slash and Burn Your Calendar

When startups achieve hyper-growth, many of the key internal processes begin to fail under the strain of a newer, larger organization. So they must be reinvented. One of the most important internal processes, but least considered, is scheduling meetings.

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The Beauty of Bottoms Up SaaS Businesses

One smart SaaS entrepreneur told me last week he prefers bottoms up businesses to top-down companies because bottoms up sales and marketing efforts enable startups to pursue hundreds of paths into a company. Unlike top down sales processes which offer a startup one shot at closing an account (a meeting with a CEO or VP), for bottoms up products, each employee is a credit-card-carrying-decision-maker.

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The Impact of Interest Rates on Startup Fundraising

In the last 35 years, the federal funds rate has varied from as high as 16% in 1981 to as low as 0.09%. throughout those cycles, venture capital has flourished from a cottage industry into $100B per year asset class. VCs are on track to invest as much capital this year as during the height of the dot com era. But, is there any observable relationship between the federal funds rate and the startup ecosystem?

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Which Open Source License Should Your Project Use if You Want to Raise Venture Capital?

When deciding to open source software, one of the key questions teams must answer is the license under which they will distribute their software. There are a wide variety of different alternatives. But, the three most common are GPL, Apache and MIT. I was curious if there was any relationship between type of license used by startup commercializing open source software, and their ability to raise capital, and exit.

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The Early Winners in the Consumer Hardware Wave

There's a "new" $4B startup today. A consumer hardware company called FitBit started trading on the Nasdaq this morning and it's an impressive success story. We've examined the tremendous revenue growth GoPro experienced in a previous post. Impressively, FitBit is growing faster.

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The Disruptive Effect of Open Source Startups

Open Source Software started the movement in the late 1990s. Since then, open source software has transformed the software industry. Today, many infrastructure software startups employ open source strategies to market their software and win dominant market share.

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Startup Best Practices 13 - Patience with Unit Economics

Financial discipline is a hallmark of great companies. It's what enables businesses to build exceptional go to market models, weather difficult times, and ultimately succeed. Sometimes, financial discipline in startups is imposed by financial markets, like in 2008 when the total amount of venture capital investment plummeted after Lehman imploded. Other times, financial discipline is imposed by founders and management teams. The tweet above is from Lew Cirne, founder and CEO of New Relic, a $1.5B market cap company serving developers, who deliberately raised small arounds at the outset of the company to impose financial discipline on his business. In other words, Lew valued patience with unit economics.

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Startup Best Practices 12 - Customer Success Compensation

Compensation structures are one of the most interesting questions facing customer success organizations in software startups. How should customer success leaders structure their team's compensation in order to align the objectives of individual customer success managers with those of the larger business?

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How an $11B SaaS Company Measures Churn

As I prepared the S-1 analysis for ServiceNow, the third largest public SaaS company in the world, I came across a section in their latest annual report called Key Factors Affecting Our Performance in which the company describes the two ways they evaluate churn. One is common, but another is unusual.

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

Worth $11.5B, ServiceNow is the third public SaaS company, after Salesforce and LinkedIn. Based in San Diego, ServiceNow employs roughly 3000 people, and sells a system of record for IT operations teams to manage IT assets, facilities, and human resources. ServiceNow's software allows clients to develop custom applications for their own needs, often with the help of the company's professional services team.

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The Expanding Role of Marketing in SaaS Companies

The role of the marketing team within SaaS has stretched from simply engendering awareness and creating interest, to guiding customers much deeper into the funnel. Steve Patrizi created the schematic above that illustrates the idea beautifully.

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Why We're Only Just at the Beginning of SaaS

We may have been talking about SaaS companies for more than a decade, but we're still just at the beginning. The legacy software companies including Oracle, Microsoft, SAP and and IBM control 83% of the market cap of software businesses, representing $830B in market cap. The largest SaaS company, Salesforce, is just about half the size of SAP, and Microsoft is 8x bigger.

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Welcome, Mina!

I'm thrilled to welcome Mina Radhakrishnan as an entrepreneur-in-residence (EIR) to Redpoint. Mina, my partner Jamie, and I got to know each other about 10 years ago at Google, where we were associate product managers all working in Marissa Mayer's APM program.

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Unpacking the Deep Diagnostic Value of LTV/CAC for SaaS Startups

In a recent podcast, Ron Gill, the CFO of Netsuite - a $7B+ market cap company with about $600M in 2014 revenue, which provides ERP software to mid-market companies - articulated the importance of the Lifetime Value / Cost of Customer Acquisition (LTV/CAC) ratio for his company. LTV/CAC is often used to justify marketing and sales investment to acquire customers. But there's much more to it.

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Startup Best Practices 11 - The 9 Box Matrix Talent Model

McKinsey developed the 9 Box Matrix in the 1970s to help GE prioritize investments across its 150 business units. Not all business units were equally attractive. Some should receive investments and others should be divested. The 9 Box Matrix evaluated business units on two dimensions: industry attractiveness and competitive strength of the business unit. At some point in the last 40 years, Human Resources teams co-opted this model as a talent management tool, and replaced the two industry axes with people specific ones: performance and potential, as depicted above.

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When Should Your SaaS Startup Offer Professional Services

As the next generation of SaaS companies achieve maturity, they have begun to serve larger and larger customers, who in addition to demanding a great product, often request services. Professional services, as they are often called, entail training and customization. For product driven startups, the decision to offer professional services is a tricky one.

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The Health of the SaaS IPO Market

Of the 43 SaaS companies to have gone public in the time period between 2006 and 2014, 60% are trading above their IPO pop price – the price at the end of their first day of trading. The median company has appreciated 69% since its IPO. The chart above shows the trends for each of the companies in this data set.

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Should You Take Cash or Stock to Sell Your Startup?

In 2000, the majority of tech acquisitions were primarily stock. One company would buy another using its own shares, instead of paying for the target business in cash. But since then, there's been a secular trend to cash deals. In 2014, 90% of the tech M&A transactions consummated by companies, and excluding private equity firms, in the US with disclosed deal values were cash deals.

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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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