Web Startup Lessons

There are not many to be found. He or she might call himself a “consulting CTO,” “freelance CTO,” “on-demand CTO,” “CTO on call,” “CTO for hire,” or just a “technology strategy advisor.” Most likely, this is a person who is a serial entrepreneur and was the chief technology officer for two or more web startups. If you find him, he’s gold, and not only because of his knowledge and experience. He’s valuable because he will work on your project on a short-term basis.

In this article, you’ll find out how a consulting CTO can help you, when to use one, and how to find the right person.

If you haven’t noticed from my web site or blog, I work as a web applications developer and a consulting CTO. So let me state the obvious: What I’ve got to say is self-serving because I want to introduce you to what I do. But I’m not the only person who does this kind of work. I’ll list other consultants I know about, as well.

Who Uses a Consulting CTO

I’m going to focus on the needs of the founders of startup companies:

• Founders of startups use a consulting CTO when they have business vision but limited knowledge of the technology needed to launch their company.

Technology executives and investors also use consulting CTOs:

• Technology executives use a consulting CTO when time is short and a project must be pushed ahead.
• Technology executives use a consulting CTO when they want to supplement their own understanding of a new technology with additional knowledge and experience.
• Investors use a consulting CTO for technical due diligence.

When to Use a Consulting CTO

Time is of the essence in launching a startup company. You have limited resources to sustain yourself as you bring the company to full funding. By deciding to use a consulting CTO on a temporary basis, you avoid getting stalled in the earliest stages. Also, working with a consulting CTO will prepare you for finding and selecting a permanent technology partner. And finally, you may be able to avoid diluting your equity.

• Avoid delay by using a consulting CTO on a short-term basis while you are searching for a permanent technology partner.
• Your consulting CTO will introduce you to the technology issues that you need to know about before selecting a permanent technology partner or hiring a permanent CTO.
• Preserve your equity by using a consulting CTO to ramp up your company before securing early-stage financing and hiring a permanent technology partner.

Why Use a Consulting CTO

• A consulting CTO can help you complete a business plan by estimating costs and timelines for the company’s technology development and deployment.
• A consulting CTO can provide the help you need to draft the preliminary mockup or paper prototype that you’ll present to investors and potential business partners.
• A consulting CTO is an expert on the current state of the technology and can suggest the most appropriate development platform for your business. For the non-expert businessperson, this means advice about “what software to use” but also guidance through the arcane arts of software development, including advice about programming languages, software development methodologies, web application frameworks, software architecture, revision control systems, and other hacker black magic.
• A consulting CTO can help you find and qualify a permanent technology partner, a lead developer, a user experience expert or interaction designer, a graphic designer, or a VP of engineering. He can help you determine whether to outsource development (locally or overseas) or build an inhouse team.
• A consulting CTO is familiar with software development best practices and can establish quality standards for software architectures, coding conventions, documentation requirements, and quality assurance processes at the very beginning of your project, ensuring that your business scales with growth and survives investors’ technical due diligence reviews.

Why are consulting CTOs so scarce?

Obviously, there are not many technologists who have had the experience of launching multiple web startups. (Though after the dotcom collapse of 2000-2001, there are many more than there were! And why would you hire a technology guy who launched a failed startup? For one thing, you’ll learn from his mistakes. Perhaps the more failures, the better? And his previous startup failures may have been the result of non-technical business issues like failure to find funding or missed market timing.)

Most of the experienced web startup CTOs are actively involved in launching new startups (often their own) and are not available for consulting. But you very well may find technology startup founders who are paying their bills by doing consulting while they develop their own projects or raise the funds they need to launch. There are also consultants who just don’t want to dedicate themselves to a full-time startup (and the lifestyle it requires) and prefer to get involved on a short-term or part-time basis. The latter includes successful technology founders who have cashed out but want to stay in the game for the fun of it.

Finding a Freelance or Consulting CTO

You actually can find a freelance or consulting CTO by searching on the web. The best ones know enough about Internet marketing (and search engine optimization) that they’ll be visible if they are looking for new projects. Try Google. Also try a search on LinkedIn.

Referrals from your investors (or potential investment partners) are ideal. If you’ve begun the process of raising capital, ask the angels or venture capital partners to recommend technologists who consult on a part-time basis. Even if you already have a permanent technology partner, your investment partners will appreciate that you are seeking additional guidance and opinions from other experienced technologists.

You can also look for CTO consultants in the same places you’ll find a lead developer: local technology user groups or meetups, conferences, and online communities (especially open-source software communities). Ask developers if they’ve been involved with a previous web startup and what their role was in the startup. They may be experienced enough to give you guidance as consultant. Beware, however! Not all software developers are suited to the role of startup CTO. Most developers tend to be partisans of the technologies they’ve used in the past and may not be able to make unbiased recommendations in determining an appropriate technology strategy for your project. Also, many software developers you meet are pure coders at heart, preferring to work from a well-defined scope and an established specification, and lacking the crucial CTO talent of transforming a project from pure vision into engineering process.

There are very few established technology consultants who offer their services as a freelance CTO for web startups. Some have tremendous experience. Here are a few I know about:

• Jeffrey Greenberg
• Aidan Fitzpatrick

and, of course, be sure to check out Daniel Kehoe and Fortuity Consulting.

If you are a technology consultant and your name should be on this list, add a comment to this blog entry or contact me directly.

This entry was posted on Wednesday, July 2nd, 2008 at 12:55 pm and is filed under articles. You can follow any responses to this entry through the RSS 2.0 feed. Both comments and pings are currently closed.