Posted by: Costanoa Venture Capital | July 9, 2015

What I’ve Learned: Two Funds and 3.5 Years at Costanoa 

By: Greg Sands, Founder and Managing Partner

As we announced the closing of Costanoa’s second fund, a $135 million fund executing on the same strategy as our debut fund, it felt like a decent time to reflect on what I’ve learned since the beginning of 2012 when I started working full-time on creating and launching Costanoa Venture Capital.

1) Venture capital is venture capital. When I left Sutter Hill Ventures after 13 years to start Costanoa, a big question from Limited Partners was, “How will you operate outside the system of a bigger firm?” Fair point. I’ve found that the business is still pretty much the same. The biggest difference in the beginning was setting an investment strategy and maintaining the high bar for quality without the benefit of an experienced group of partners. Saying no because it’s the right answer (even if you want to yes) requires a ton of discipline. Clearly, there are some additional tasks, such as fundraising (see below), but the value creating parts of the business – finding great entrepreneurs, doing your homework, selling ourselves as a partner, and actually being a great partner – are darn near identical.

2) Entrepreneurs are our customers; Limited Partners (LPs) are (the equivalent of) shareholders. It is tempting for a new venture firm to focus on appealing to their investors and to design the firm for that purpose. PR and big social events, for example, make investors think that somehow, “this time it’s different”1, but venture firms still have reputations more than they have brands. How we work with portfolio companies remains the key ingredient not just in helping build valuable companies, but also in the referral network that helps us see and win the next great opportunity.

3) Focus, focus, focus. The entire venture industry preaches focus to portfolio companies but doesn’t much practice focus itself. In our case, we are focused on business- to- business software (data driven applications and infrastructure) and true early stage rounds. We know who we are, where we fit and why we win. We are well calibrated on the universe of early stage opportunities and have depth in our sectors. We love helping companies bring initial product to market, find product market fit and move quickly through the initial phases of the sales learning curve. We do want typical venture ownership of 20%, which doesn’t fit every investment opportunity, but when it does, companies know they’ll have our attention.

4) As in all things, alignment matters. The kinesthetic chain of a company aligns target market, problem definition, product, and go-to market strategy. An enterprise-focused startup with a full featured product and field-based sales team is very different from a mid-market focused company with an inside sales approach and a product with limited features that is easy to deploy. In a venture firm, the key components of the kinesthetic chain are team structure, fund size, typical investment size (dollars and ownership), engagement model with portfolio, and sector focus. Starting Costanoa has made me think through and articulate our strategy in a completely different way. We’re focused on B2B software and Series A (and Seed) rounds. We typically invest $2-5 million in the initial round and are well reserved afterwards to support companies throughout their lifecycle. That means we’ll make about 15 (core) investments in a fund and roughly five per year at our current scale. We typically join boards and aspire to be the most active and engaged investor, especially during the early phases of a company’s life. As products need market fit, entrepreneurs and their investors need to be a good fit, so it’s important to be clear about what we do.

5) Radical transparency works. The world has changed from a time when venture capital firms sat up on Sand Hill Road and bequeathed capital upon a few companies. Not only are there more sources of capital and competition amongst investors, but the open discussions on blogs and social media platforms mean entrepreneurs know more than ever before about their potential investors. I experienced this early on when we wrote about cloud-based infrastructure (as well as SaaS) and began to see networking and datacenter systems opportunities. We shifted the language to talk about data-driven infrastructure and started seeing companies more in our sweet spot – security, management and the data stack. Similarly, when we published an article on The Missing Slide, we quickly began to see companies incorporating it into their presentations.

Part of the idea of founding Costanoa Venture Capital was to try some new things and thereby change my own learning curve. I’ve learned a lot in the last 3.5 years, including the affirmation of some of the core principles I was taught growing up in the business at Sutter Hill. To our current and future portfolio, I say, “May the next 3.5 years provide as much experimentation, learning and growing together.”

1 According to great investor and philanthropist Sir John Templeton, the four most dangerous words in investing.

Posted by: Costanoa Venture Capital | July 7, 2015

Costanoa Venture Capital Raises $135 Million Second Fund

Costanoa VC-transparent

PALO ALTO, CA—(July 7, 2015)- Costanoa Venture Capital, an early stage investor in cloud-based services for businesses and consumers leveraging data and analytics, announced today that it has closed its second fund. The fund was capped at $135 million and brings the firm’s total capital under management to $325 million.

“We’re thrilled to have Fund II closed. The support from our Limited Partners is a vote of confidence and affirmation of our approach. It is characteristic, but it is much more important that it enables our work with another group of fantastic entrepreneurs,” says Founder and Managing Partner, Greg Sands.

“With the closing of our Second Fund, we have the capability to devote our time and resources toward partnering with exceptional entrepreneurs within our core themes and areas of expertise,” adds Neill Occhiogrosso, Partner.

Founded in 2012, Costanoa Venture Capital’s mission is to be a hands-on, value-added partner to early stage entrepreneurs in its core sectors. The firm has maintained its focus on providing Series A and Seed investments to entrepreneurs building technologies that seek to capitalize on the shift towards a data-driven, cloud-based, and mobile-centric world. Costanoa has invested in four companies out of the fund to date including Alation, Apptimize, Bugcrowd, and Directly.

“Costanoa’s investment team has demonstrated that they can provide the tools and advice to help companies grow and be successful from the start. We were thrilled when Costanoa led our Series A funding and are grateful for their partnership,” said Casey Ellis, CEO at Bugcrowd.

“Our perspective remains unchanged from our debut Fund; we strive to provide direct guidance while allowing entrepreneurs and CEOs the freedom to operate, improve and ultimately succeed,” says Sands.

About Costanoa Venture Capital

Costanoa Venture Capital is an early stage investor focused on cloud-based services solving real problems for businesses and consumers by leveraging data and analytics. Costanoa provides early stage entrepreneurs with a combination of “right-sized” amounts of capital and value-added support from a high-quality institutional partner. Current investments include: 3scale, Acme Technologies, Alation, Apptimize, Bugcrowd, Directly, DemandBase, Gamechanger, Grovo, Guardian Analytics, Inflection, Intacct, Kahuna, Lex Machina, NovoEd, Return Path, Risk I/O, Stitch Labs, VictorOps and VigLink. The firm is headquartered in Palo Alto, CA. For more information, visit and follow us on Twitter @costanoavc.

Posted by: Costanoa Venture Capital | June 15, 2015

The Real Silicon Valley

By Greg Sands, Founder and Managing Partner

Every time I hear people talking about unicorns, I think “all hat, no cattle” or “another person living in the land of style over substance.” I’ve found myself blurting out, “F$&@ Unicorns!”* twice recently, including when I was on a panel at Stanford School of Engineering onEntrepreneurship from Diverse Perspective. (Yes, I get the irony.)

It’s not that I don’t like billion-dollar companies.  Believe me, I like them as much as the next guy.

When Datalogix was bought by Oracle or when Yokou went public, it felt like great validation from years of hard work that came before it. I was thrilled for the teams that had worked so hard to build the business and proud of my involvement, even if the role of an investor is somewhat limited relative to the founders and management team.

When Netscape went public on August 8, 1995, I was sitting around the table with our engineering team and it instantly changed the life of the team. While those exits were milestones in my career, I am really pleased that our investment strategy at Costanoa, including the size of our fund, doesn’t require that we can only invest in unicorns. (For more on this subject, please see the well-written piece by Todd Hixon on how smaller funds can build a venture portfolio that can make money in a broad range of outcomes.)

I think my level of emotion on the subject is a function of how the press and media distort the real Silicon Valley. As I said at the panel, “If you get all your information on the entrepreneurial ecosystem from HBO, you’re screwed.”

The notion that gets propagated through the media is that Silicon Valley is the land of the fast and loose, where everyone is shallow and trying to make a buck (or a billion of them) as quickly as they can. Yes, it exists, but they aren’t the majority. The investors and entrepreneurs I have worked with do not encompass that stereotype at all.

Most of the people I know in Silicon Valley are hard-working, substantive and dedicated to building their products and business. They want to work on problems they are passionate about and they want to work with teams of people they love. And most companies, even the successful ones, are filled with moments of anguish and ecstasy. As former Netscape CEO Jim Barksdale said to us, “Our purpose here isn’t to make money. Our purpose is to acquire and serve customers. Making money is the logical consequence of doing our jobs well, but it isn’t our purpose.”

If you’re in the business of building companies, focusing solely on the unicorns will get in the way of executing on the high-priority items right in front of you. It is understandable that unicorns get outsized focus from outsiders, press, analysts and even LPs who observe the “inner workings” of entrepreneurial companies only when they’re doing well and nicely packaged by a PR team.

But life inside startups is messy. Most successful founders have to grind through periods of difficulty, face moments of apparent doom, and think their way through complex and multi-layered problems.

It’s okay that outsiders don’t understand the sausage making, but when entrepreneurs and venture capitalists who ought to know better focus on a “play” in gaming, a “deal” rather than an investment, or a “unicorn” rather than a company, they misinterpret — and understate — what Silicon Valley really is and why it is the biggest driver of innovation in the global economy.  So saddle up, people, and get back to building companies…

*This post is not intended to offend my friend, Aileen Lee from Cowboy Ventures, who coined the term. She is a great investor and partner to entrepreneurs, who doesn’t take her job or responsibilities lightly.

This post originally appeared on Techcrunch.

Posted by: Costanoa Venture Capital | May 19, 2015

The Arrival of On-Demand in the Enterprise

By: Greg Sands, Founder and Managing Partner & Bucky Moore, Investor

With the first annual On-Demand Conference happening today in San Francisco, we are excited to highlight the opportunity for on-demand services to meet critical business requirements. We’ve been observing (and hopefully helping catalyze) this movement at Costanoa, and are thrilled to announce our Series A investment in Directly.

We can agree that our lives as consumers continue to undergo a transformation driven by “on-demand” services. Lyft, Instacart, and Deliv have built and scaled networks of part-time workers to deliver goods and services quickly and cost-effectively. AirBnB, ClassPass and others have created new markets on top of excess supply. We believe there is an equivalently large opportunity taking shape in bringing these business models to the enterprise.

Companies like LiveOps were early pre-cursors to what we now consider enterprise focused on-demand services. They built an impressive business, even though they had a hard time breaking out of their core vertical in direct response call centers. The next generation of services and companies is being created now and is ready to partner with enterprises that are engaged with a remote and flexible work force.

We are already observing this begin to play out in a number of key business functions. One example from within our own portfolio is, Bugcrowd, a provider of crowd-sourced security testing solutions for the enterprise. By enabling a community of over 16,000 cyber security researchers to “hack” on their own time, BugCrowd is able to deliver superior results than traditional penetration testing consultants at a significantly lower cost. Companies like uTest, Upwork (formerly known as Elance/oDesk), Workfusion, and HourlyNerd are also part of the first wave of companies bringing “on-demand” into the enterprise. They each represent a software layer that manages and orchestrates a community of skilled, part-time workers capable of serving as outsourced labor for specific functions within a company. Be it in QA, design, finance, or data collection, these platforms are forcing businesses to think about who should really be handling the “long-tail” of tasks by making outsourced labor readily accessible and easy to manage.

The question is, why now?

First, the global workforce continues to grow more talented and skilled. While there has historically been skilled labor in a variety of countries, they were disconnected from the Western, developed economies. With the proliferation of connectivity and computing power (including in mobiles phones), these workers can now participate in the worldwide technology economy. Second, the sophistication of the collaboration tools we have makes distributed teams far more productive. “Remote worker” doesn’t have negative connotations to companies using tools like Slack, Hangouts, and Trello. The most effective marketplaces contain tools for freelance workers to collaborate and combine their respective expertise to deliver a complex and integrated service. Third, the success of on-demand companies in the consumer space has shown that workers are able to generate meaningful income, whether full- or part-time. We see the potential for the same to be true for increasingly specialized labor. The economic opportunity combined with the freedom and flexibility of freelance work will pull people with specialized skills into these markets. The best marketplaces will even invest in creating and developing the specialized skills necessary for success.

There are enormous operational benefits that come with tapping into part-time labor. Enterprises already spend billions annually with companies like IBM Accenture and Infosys to get lower cost and variable infrastructure by outsourcing functions like IT, and customer support, but it comes with significant tradeoffs in quality. For example, customer support delivered by outsourcers typically reduces customer satisfaction. In contrast, on-demand services for the enterprise have demonstrated the ability to increase quality AND reduce cost. This is why we are thrilled to announce our partnership with Antony, Jeff, and the rest of the Directly team. Customers of Directly who have interacted with their “elastic” service teams, for example, report higher average customer satisfaction (CSAT) scores for cohorts served by employees or outsourcers. Its routing technology sends customer questions and help desk tickets to expert users on their smartphones, and then rewards them for resolving the issues. In fact, customers including Pinterest, AirBnB, Udemy, Lyft and Republic Wireless have resolved nearly 500,000 customer service inquiries via the Directly platform to date. Similar to the way bug bounty platforms are changing the security landscape, we believe Directly’s on-demand service platform will transform the way enterprises service and interact with customers. In addition, the platform provides a workforce capable of scaling up to meet spikes in demand. For fast growing companies, using on-demand services might be the only way they can keep up with customer inquiries.

We believe that today’s Enterprise On Demand companies are just scratching the surface of what is possible — that the benefits of marketplaces, orchestration tools and an elastic workforce will soon undertake tasks that simply could not be done easily by employees.

For more information about Directly’s Series A announcement, read the press release here.

Posted by: Costanoa Venture Capital | March 31, 2015

Stealth no more: revealing Alation

By: Greg Sands, Founder and Managing Partner


Three weeks ago, I wrote about Alation’s funding. This week is even more exciting since we actually get to talk about Alation’s product and its customers.

Alation accelerates analysis by helping people quickly find, understand, use, and govern data. It centralizes the knowledge of an organization’s data, without forcing the organization to consolidate the data itself.

Alation’s platform approach delivers what data-driven organizations have been trying to achieve for decades – collaborative analytics, data search and discovery, effective data governance, and data warehouse optimization. Many approaches have been tried to solve this 25 year- old problem—and it has only gotten worse as sensors and clickstream data have proliferated and the modern Big Data stack has emerged. Software-as-a-Service (SaaS) applications have enabled business teams to go around IT in rolling out new capabilities quickly, but they make the challenge of finding, using and governing enterprise data that much harder. Data Sprawl, the inability of analysts to find the right data and understand what it means, is a central problem for all data driven organizations.

Organizations and vendors have tried to solve this problem many times. Centralizing all the data quickly becomes prohibitively expensive and limits the agility of technology solutions and the IT team in solving business problems. Asking users to document the data (create meta data) and keep it up to date to make assets searchable is too burdensome. Alation uniquely combines the power of machine learning with human insight, automatically capturing what the data describes, where the data comes from, who’s using it and how’s it’s used.

The objective all along has been to make data more accessible to both analysts and programmers, so that they can find and understand the right data and use this data to get insight for better business decisions. Instead of locking data assets behind a glass wall, Alation fosters faster collaboration between analysts, stewards, business users, and IT by enabling them to share knowledge, exchange ideas, and quickly find answers with an intuitive set of interfaces, depending on role.

Alation is an elegant solution that delivers tools that look like search for enterprise data and a computer-generated wiki (e.g. Wikipedia) for enterprise data. Delivering on that promise is incredibly hard and requires doing a lot of critical foundational work first. Most importantly, it requires integrating directly with key data sources – that is, Alation inserts itself into the query stream for major data warehouses and applications to extract data (and meta-data) and auto-generate a wiki. Slapping a UI layer on top of existing data assets and meta-data simply won’t solve the problem.

One of the things this announcement helps me realize is the pride that I take when our portfolio companies deliver extraordinary customer value. To me, the best part of today’s announcement is that several happy Alation customers have stepped forward to share how they are using and getting value from Alation. That true north is the best metric (even better than sales) about whether the company is focused on the right things. The use cases of eBay, MarketShare and Square are exciting proof points about the capabilities that Alation is enabling. Onward!

For more information, read the press release here.

About Alation
Alation’s enterprise data accessibility platform empowers employees inside of data-driven organizations to find, understand, use, and govern data for better, faster business decisions. Alation combines the power of machine learning with human insight to automatically capture information about what the data describes, where the data comes from, who’s using it and how it’s used. Alation is based in sunny Redwood City and funded by Andreessen Horowitz, Bloomberg Beta, Costanoa Venture Capital, Data Collective and General Catalyst Partners. Customers include eBay, MarketShare, and some of the world’s largest finance and retail firms. For more information, visit

Posted by: Costanoa Venture Capital | March 12, 2015

Our investment in Bugcrowd

By: Neill Occhiogrosso, Partner & Bucky Moore, Investor


Today, Bugcrowd announced a $6M Series A financing, led by Costanoa Venture Capital, with participation from existing investor Rally Ventures. As part of our investment, I have also joined Bugcrowd’s board of directors.

I wrote about our interest in security in October. In the short time since then, a number of large-scale breaches have occurred, including the famous ‘Sony Hack’ and a massive online bank robbery. The problem continues to get worse, and companies are scrambling to protect themselves with the latest and greatest security technologies. This problem has produced several notable startup successes including Palo Alto Networks, Splunk, and FireEye. However, despite their increased vigilance and spending on technology, there is one problem that chief information security officers (CISOs) can’t buy their way out of: talent. There are more than 200,000 unfilled cybersecurity jobs and open job postings have increased by 74% over the past five years.

Pioneered by Netscape, and refined by large web companies like Google and Facebook, bug bounty programs have emerged as a way for security teams to leverage talent outside of their companies, and continue to gain mainstream adoption. By offering financial rewards to security researchers who discover vulnerabilities in their systems, organizations are able to harness the power of crowdsourcing to have more security experts, working on their behalf, exactly when they’re needed. While these programs have been in existence amongst large web companies for some time, running such a program has been very difficult for “the other 99%” of companies until very recently. Bug bounty programs not only require a unique software platform, but also the resources and expertise to review and process the high volume of submissions that a well-run program will generate.

This is why Costanoa is absolutely thrilled to be partnering with Casey, Chris, and the rest of Bugcrowd team. Already counting Pinterest, Blackphone, Western Union and Aruba Networks among its customers, Bugcrowd gives companies of any size the ability to run bug bounty programs, and access to their globally distributed team of 15,000+ researchers. They have built a unique, end-to-end platform offering a turnkey solution for running and managing bug bounty programs, while also curating a diverse community of security researchers that are intelligently matched with companies based on their specific expertise.

We are very excited about the profound impact that Bugcrowd is having on the security industry, and look forward to building a great company together. If your company is interested in getting started with a bug bounty program, learn more and get started here.

For more information, read the press release here.

Posted by: Costanoa Venture Capital | March 4, 2015

Our investment in Alation

By: Greg Sands, founder and managing partner


One of the challenges of the venture business is that sometimes we make an investment in a company that we’re really excited about- and then can’t talk about while it builds initial product and makes early customers happy. While we are only announcing the financing today, Costanoa is thrilled to finally be able to talk about Alation and hint about its contribution to solving the problem of data sprawl in enterprise environments.

One of the things that excites us the most is working with truly great people. This is a founding team that fits us – and each other – so well.  Satyen Sangani integrates product leadership for a highly technical product with great go-to market instincts and is a natural draw for great people. He is unequivocally thinking his way through the problem (see The Sales Leader or the Chess Master).  Venky Ganti and Feng Niu provide outstanding technical leadership – both the ability to solve really hard problems and to act as Pied Pipers, attracting unique technical talent that wants to work on really hard problems. Finally, it says something about the company that Aaron Kalb is a co-founder and lead designer in a company that’s addressing how to organize and find enterprise data to get to insights faster.

Alation is addressing a huge problem that is only getting worse.  For decades, business analysts and SQL developers have struggled to find the right data, figure out what a given field means or what manual adjustments had been made to it. Companies have been trying to solve these problems by creating data warehouses to achieve a “single source of truth” – but to little effect.

I remember looking at solutions for Enterprise Data Integration (search for data) and Master Data Management (wiki for data) over a decade ago.  None of those solutions solved the core problem of data access and analyst productivity.  Since that time, the scale of enterprise data has increased by an order of magnitude due to more automation, increased sensors, the rapid increase in web and mobile clickstream data, increased compliance requirements, and the ease of spinning up a database.

This is the problem space into which our friends at Alation are wading. We look forward to telling you more soon.

For more information, read the press release here.


Posted by: Costanoa Venture Capital | February 17, 2015

Welcoming Apptimize

By: Neill Occhiogrosso, Partner

We are thrilled to announce our recent investment in Apptimize and welcome Nancy Hua, Jeremy Orlow and the rest of the Apptimize team. Apptimize lets mobile teams instantly change their native apps for optimization, targeting, and A/B testing.

At Costanoa and at our prior firms, Greg and I were fortunate to participate in the digital marketing revolution with companies like Acquia, Conductor, QuinnStreet, and DemandBase. It’s a space that we know well, and where we think there are many more terrific companies to be built. Apptimize is squarely focused on mobile, one of the unassailable mega-trends in IT today. Like most people, I’m bullish on mobile, but I was still surprised to see the astounding rate at which e-commerce spending is moving to tablets and phones. With their recent Instant Update product launch, the company has hands-down the best product in their market and while the best product doesn’t always win, it sure helps!  The team is incredibly smart and maniacally hard working.  It’s a pleasure to be around them and feel their energy, and we look forward to the amazing things they’ll achieve. Apptimize: Welcome to Costanoa!

Apptimize Raises $4M in Series A Funding to Bring Revolutionary Iteration Speed to Mobile Apps

Menlo Park, CA—February 17, 2015- Apptimize, provider of optimization tools for mobile applications, announced today that it has closed a $4 million Series A funding round led by Costanoa Venture Capital. The Series A round brings Apptimize’s total funding to $6 million, after a $2.1 million seed round in January 2014. The new funds will further revolutionize the mobile development process by enabling product managers, designers, marketers, and developers to make instant updates to any mobile app without having to code or redeploy their app.

“Apptimize is leading and changing the way mobile apps are optimized,” said Neill Occhiogrosso, Partner at Costanoa Venture Capital. “This is the reason why top companies like Vevo, HotelTonight, Glassdoor, Strava, and Flipagram have chosen to leverage Apptimize to iterate faster and with real user data.”

Mobile is changing at an incredible rate, but mobile app development is one of the slowest things out there. Apptimize is solving this by letting mobile app development teams get continuous data-driven deployment without sacrificing the native experience. Traditionally, mobile app development is a slow process because the development, QA, and deployment cycle take 6-12 weeks for a fast moving app.  In order to get faster iteration speed, some apps have opted to integrate non-native components into their app (HTML) at the sacrifice of performance and user experience.

“Apptimize cuts app iteration time down from months to minutes. Now, mobile product mangers can push out a change instantly and immediately start gathering data on whether or not that change made a statistically significant improvement to the app before spending weeks coding,” said Nancy Hua, Apptimize CEO.

“We’ve been able to move faster, iterate faster, and take a few more risks,” says Audrey Tsang, Director of Product of HotelTonight.

“What made me excited about [Apptimize] was the ease by which we could make a change to this new app that just got launched and unlock the whole potential of building things more quickly,” said Jon Li, Senior Director of Product at Vevo.

About Apptimize:

Apptimize is a high performance, reliable way to optimize native Android and iOS applications. With robust A/B testing, Instant Updates, and a codeless installation process, Apptimize empowers anyone on a mobile team to push changes to users in real-time and A/B those changes without App or Play Store approvals. Apptimize also offers a programmatic interface that enables app developers to test anything they can code. Other key features include powerful analytics, feature flagging, staged rollout, results segmentation and filtering, and advanced targeting. For more information visit

About Costanoa Venture Capital:

Costanoa Venture Capital is an early stage investor focused on cloud-­based services solving real problems for businesses and consumers by leveraging data and analytics. The firm’s name originates from the first inhabitants of Silicon Valley, the Costanoans, and harkens back to the origins of entrepreneurship and venture capital in Silicon Valley. Costanoa provides early stage entrepreneurs with a combination of “right­sized” amounts of capital and value ­added support from a high­ quality institutional partner. Current investments include: 3scale, DemandBase, Gamechanger, Grovo, Guardian Analytics, Inflection, Intacct, Kahuna, Lex Machina, NovoEd, Return Path, Risk I/O, StitchLabs, and VictorOps. The firm is headquartered in Palo Alto, CA. For more information, visit read and follow on Twitter @costanoavc and @gsands.

Posted by: Costanoa Venture Capital | February 17, 2015

The Four Stages of the Learning Curve for Young Companies

By: Greg Sands, Founder and Managing Partner

A startup team has accomplished two important goals out of the blocks: 1. they’ve spent the time finding a market and problem space that is big enough to satisfy their ambitions; and 2. they’ve engaged deeply with prospective customers to understand requirements and priorities to build a product that solves a significant problem. What’s next?

About once a week, I hear an entrepreneur during a financing presentation tell me that the product is almost ready for General Availability. They say, “Now all we need to do is hire a sales guy.”  It’s a little bit of an overstatement to say that the meeting ends at that point, but suffice it to say that I know I am dealing with someone who doesn’t have any idea what to do next – and as a result, we are very unlikely to invest.

Enterprise-focused software companies need to take a learning approach to their sales and marketing process if they want it to be scalable and capital efficient. The next stage of a startup, the sales learning curve (SLC), can be both thrilling and terrifying. And even though getting the first product to market is less expensive than ever, it can create or destroy value at high speed because the “go-to market” (sales and marketing) can still be extremely expensive for Software as a Service (SaaS) and other enterprise- focused companies.

Below are the four key stages of my version of the Sales Learning Curve built for early stage companies just shipping their initial product. This process can be used for any new product as well. I use the analogy of industrial development because it makes clear and basic principles like process standardization and scalability.

  1. The Craft Economy—Founder-led selling

Sales in early stage companies shipping 1.0 products is too important to be left to sales people. Founders* have several key advantages critical for early selling—they are involved in creating the product so they know the product and market it serves deeply; their charisma, brilliance and Reality Distortion Field can help overcome the disadvantages of having a new product of a new company; they carry CEO/Founder business cards which opens doors and looks impressive (if they bother to wear closed toe shoes and long pants); and they sell at the white board, sometimes making up new products or committing to new features in a meeting. In addition, this is an essential way to get early product feedback while the company is honing in on Product Market Fit. Feature requests and rejections from potential customers are the fuel for the next phase of innovation. I find that Founders and CEOs are uniquely good at interpreting this early product feedback and synthesizing what needs to be done to be productive.

* sometimes early product managers or CTOs can play this role as well

  1. The Sales Apprentice—Business Development as Sales

When the Founder/CEO has successfully found a pattern of successful sales, it is tempting to say, “Now it is time to hire a traditional coin-operated sales person to scale up this process,” but that rarely works. I’ve seen companies hire a salesperson from a competitor or incumbent and not sell anything. Even worse, I’ve had the experience (as a board member) of hiring “exactly the right” VP of Sales, (she worked previously in an adjacent company for a former colleague so I could reference closely) and she hired a team to scale up the process. It was a very expensive mistake, but it wasn’t the fault of the VP of Sales. The company had very few things a mature company has– like sales materials, marketing air cover, a real price list, and inbound leads. By contrast, the highly charismatic CEO could “sell ice cream to eskimos”- so the handful of early (and big) sales was not an indication that a mere mortal could do the same.

In contrast, the most successful example I’ve seen was at Merced Systems, where I was fortunate to be the only venture investor. Founder and President Mark Selcow sold the first half dozen deals himself and then hired a young, smart and hungry Sales Apprentice. The Apprentice learns from the Founder, but doesn’t assume he can simply replicate the process. He doesn’t have Malcolm Gladwell’s proverbial “10,000 hours” in the domain, the stature or oftentimes the natural charisma. His job is to run experiments and see how he can map the founder’s successes onto his own pitch, skills and process. The Sales Apprentice has to be smart and humble enough to learn from all this experimentation to find a process that can be scaled up successfully. Oftentimes, this person is a mid-level Business Development hire rather than a traditional coin-operated sales rep. Business Development in more mature companies still involves investigation with potential partners, typically deeper product knowledge and tends to attract people who want to create a new process rather than follow an existing one. In the modern parlance, this might be a “sales ninja” (see Bloomreach CEO, Raj De Datta’s piece on this subject), but a sales ninja doesn’t tell you what to do before or next.

  1. Light Manufacturing

At this stage, the company is ready to TRY to standardize the process with a few traditional sales people. I emphasize ‘try’ because even if the company has been through the first two stages, there is no guarantee of success- and the focus has to remain on the learning curve. I’ll also note that the sales team is an important principle. In today’s world where a great deal of selling is handled inside (or over the phone), startups that have 2-4 people in a single location—even a bullpen—challenging and learning from each other can accelerate the rate of learning.

Ideally, the first true sales people come from adjacent companies or segments. I differentiate “true sales people” from Business Development because they’ve been on quota all their life and once they figure how to make a sale, they want to go as fast as they can rather than invent a second new way to sell. The first hires are often people who want to be early in a company’s life and have honed the skills to do so. The Sales Rep from Oracle who has been selling with that brand and machinery behind him is unlikely to be successful at this stage. Early stage sales people like learning a bit more about product and are comfortable iterating their own positioning, presentation and scripts (for inside sales). Their high energy lets them run many experiments- making a lot of calls into different customer types and with different pitches. While the Apprentice is focused on making their product (in this case, the sale) themselves, the first sales team is “engineering” the first sales factory. They are employing to the method developed in stage two, beginning to standardize it, and continually tweaking, improving and optimizing the process. Building from the first rep to the first team of reps (5-10 people), who are closing business and hitting their quotas, is where you start to see the unit economics of sales and marketing.  Once you have them dialed in, you are ready for the final stage, heavy manufacturing.

  1. Heavy Manufacturing

Once the company is generally hitting sales goals, knows the levers to improve and scale up the sales/marketing process and its unit economics (Customer Acquisition Cost/estimated Lifetime Values), they are ready to accelerate. In fact, the company is ready for the bigger equity round that gives you the resources to do so. Stepping on the gas has several forms, from gentle acceleration to rocket boosters, which is largely driven by how good the unit economics (again, CAC, LTV) are. However, it is important to note that some acceleration may be appropriate even when the numbers are just “OK” since this phase is all about learning to improve it.

This final stage is where the company moves into the process of optimization and scaling at an even higher velocity — developing a hiring profile, training and onboarding program, standardizing the sales process materials, improving close rates and the accuracy of forecasting. This is where the team is increasingly fed leads by marketing or a sales development team, which qualifies leads inbound leads and does outbound prospecting. This final stage also requires significant development of all the adjacent functions. Arguably the first job of marketing is sales enablement and getting the sales team “selling on PDF” where the sales materials are completely standardized so the company can deliver consistently and efficiently. Sales operations becomes a real job.


Taking a learning approach to selling is like building a solid foundation for your house—it’s safer and more capital efficient. Do it right and the entrepreneur can build a very big company—and one that the founding team owns much more of than they would if they took the “go big or go home” approach. Even if “go big” is the orientation, knowing where a company is on the Sales Learning Curve will help an entrepreneur make better decisions and grow more efficiently. And I assure you, venture capitalists will highly value a company’s knowledge of and approach to build the sales machinery. Growth equity investors, who typically pay higher prices than early stage investors, love nothing more than a “just add water” company where the go-to market process is well defined and has good unit economics. They know such a company can use the new capital with high confidence to grow faster. As a result, focusing on the Sales Learning Curve is the way to increase the value of your next round and the long-term value of your company.

*Mark Leslie’s Sales Learning Curve in the Harvard Business Review uses a different nomenclature and is a much more detailed article based on his experience building Veritas Software and as a Silicon Valley board member. I highly recommend it for further reading.

A version of this post originally appeared on VentureBeat.

Image Credit: Frank Fiedler/ShutterStock

Posted by: Costanoa Venture Capital | October 26, 2014

Security Will Need Big Insight, Not Just Big Data

Guest Post by Neill Occhiogrosso

In looking for new opportunities in security and many other sectors, we look for the echoes of the current IT mega-trends: cloud, mobile, big data. These trends, and especially the interactions between them, are dramatically changing security needs. Add to that the changing profile of would-be hackers — now a frightening mix of international organized crime and employees of enemy governments — and we see the potential for several new solutions that can each be the foundation of one or more successful companies.

The first is the application of big data technologies to produce security insights. This is a classic example of “Applied Big Data,” the application of new analytic technologies to a current business problem. Security professionals are drowning in log files, vulnerability scan reports, alerts, reports, and more, but the data is not actionable.

This isn’t an idle observation: Several high-profile breaches happened through vulnerabilities that had been documented months or sometimes years prior. The future lies in analyzing this data to give security professionals a comprehensive view of their security posture. Tell them what is at risk, how severe the risk, how important the asset is, and how to fix it. We see tremendous promise in Risk I/O’s approach to this problem, and we’re proud to have led their most recent investment.

Another area for exploration is security solutions that follow assets to protect them wherever they are. With cloud infrastructures (both public and private) and bring-your-own-device mobile enterprises, there is no perimeter and every layer of the stack is dynamic. Security professionals need to be able to apply security policies to applications, data, and users wherever they are, and those policies need to adapt based on the changing context.

There’s an increasingly popular saying that there are two types of organizations now: those that have been breached, and those that just don’t know it yet. As attacks have become too sophisticated for signature-based detection, there is a need for solutions that quickly notice anomalous and potentially dangerous behavior (likely leveraging machine learning) to prevent breaches or — failing that — detect malicious behavior once a breach has occurred, and minimize its impact.

Guardian Analytics, another Costanoa investment, applies behavioral analytics to data already resident in online banking platforms to prevent a broad range of fraudulent activity. This is just one example of applying data science to existing data sets to address more nebulous threats. There will be more opportunities looking at different applications and different types of attacks.

Finally, there is also the need for efficient data capture and analysis that can look broadly and historically across an infrastructure, sometimes trailing several months, to see when and how a breach occurred, and what the consequences were. This is a prototypical big data problem. It involves great volume, variety, and velocity of data.  It now may be tractable, and we are on the lookout for solutions.

We live in an exciting time, but unfortunately in the case of security, that is a double-edged sword. New technologies present new opportunities for criminals. We are optimistic that great new companies are emerging to rise to the challenge.

This post originally appeared on TechCrunch.

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