NextNY CTO School

Fall 2010

Session 1 – What is CTO

 Before We Start

Your Mileage May Vary

For Everything We say
 Today’s Agenda
• CTO vs. VP Eng vs Dev Lead
• What Skills Are Needed and Why
• A Bit More On Technology Skill
• Being Part of Executive Team
• Tips & TriX
 CTO School – S2
• 10/11 (Mon) S2 -  Key Technical Decisions
– Key Technology Decisions
• Languages & Platforms
• Persistence
• Web Layer
– Technology decisions related to your startup
• Prototyping
• Development Tools Overview
– Key Technical Building Blocks You Should Know
About
 CTO School – S3-S5
• 10/27 (Wed) S3 – Process - Getting Technical Stuff Done (and Well)
– Development Process
– Project Management for CTOs
– Security
– Quality Assurance
– Estimation

• 11/8 (Mon) S4 - Deployment Infrastructure & Operations

– Picking hosting environment
– Server technologies - app servers, load balancers, proxies, caches, storage, etc. 
– Disaster Recovery and Backups
– Running Production Systems

• 11/22 (Mon) S5 - Scaling Everything

– Yourself & Your Team
– Hiring
– Your Product
 About Me:
• CTO / VP. Eng / Lead Architect
EnergyScoreCards.com
– Benchmark, Measure, Verify Energy of Buildings
– Market: Real Estate Portfolio Owners (B2B), Energy Efficiency Programs
(B2G)
• Technology:
– Groovy / Grails, Java
– Tomcat
– MySQL
• Product Team Size:
– 2 NY (me and Analytics / QA person)
– 4 Outsourced to Ukraine
 Jean’s Background
• Jean’s Done / Been / Am
– Technical Consulting - many projects, technologies, and business needs.
– Technical Lead of a small team
– Trainer
– Software Architect
– Developer on a Product Team
– Writer
– Public Speaker
– Project Manager

• Proudest Accomplishments
– Got 20 Fresh-Out-Of-College to go from zero to completed project in six weeks. 3
Times!!!
– Launching FordDirect.com as Tech Lead 18 months out of college
 About Pete:
• CTO, Knewton.com
– Creating an Adaptive Learning Platform
– Market: Starting out in Test Prep. Looking to expand.
• I’ve Done / Been / Am
– Technical Lead of Research and Development
– Manager of Medium Size Engineering Team
– Managed Large Product Development Organization
– Developer
– Customer Advocate
– User Experience Advocate
• Proudest Accomplishments
– Turning Recent College Grads into great developers, shipping product in weeks.
– Moving from a 1 month to deployment cycle to 1 day for a critical infrastructure system
– Taking a complex product from vision to launch in fewer than 6 months
 Typical Day
• Morning – From Home
– Respond to Proposal
– Talk to Team in Europe (4 people)
• Discuss status
• Assign New Tasks / Talk through Design
– Fix two bugs
• Afternoon - Come in Office
– Dev Meeting.
– Deep-dive into some issues
– Try to do some hiring (interview or try to reach out)
– Follow up with tech team from potential partner
• Late Night – Home
– Review quote for a sale
– Review some new code from team in Europe
– Finish coding a new feature
– 2am – put up a new build

• Observation: Lots of Context Switching. Barely any “actual” work.

 CTO vs. VP Eng
Support the business strategy of your business by formulating and
executing technical strategy.

• CTO - Technical Vision

• “Great CTO’s usually can’t manage their way out of a paper bag, but have huge vision, the ability to pull an all-nighter and crank out a rough prototype
of the thing they are thinking about, have the unique ability to translate complex / abstract thoughts into simple English that a non-technical end-user
can understand, and a willingness (or even desire) to get up in front of 1,000 people and talk about the latest greatest thing they are working on /
thinking about. They are also perfectly happy to work collaboratively with the VP Eng while leaving the engineering team completely alone”

• VP Engineering – Technical Execution

• Process / management gods (and goddesses) – totally focused on building and shipping products.  Most of them are “medium technical” – strong
enough to stand up to the engineers they manage, but not necessarily the best coders on the team.  A few were rock star developers; a few were non-
programmers (i.e. “anymore”)

Source: Brad Feld

http://www.feld.com/wp/archives/2007/10/cto-vs-vp-engineering.html
• http://www.bothsidesofthetable.com/2010/04/19/want-to-know-the-difference-b
etween-a-cto-and-a-vp-engineering/
 CTO Role in Different Organizatoins
• Infrastructure Manager
– IT in a support function
• Technology Visionary & Operations Manager
– Startups & Technology Companies
• External Facing Technologist
– Technology is used to provide products & services to customers / partners
– Customer-Focused Technologist
– Market research & key customer focus
• Big Thinker
– Evaluate how technology can be used to create new business models / products
– Advanced technology, competitive assessments, prototyping

• (Werner Vogels) http://www.allthingsdistributed.com/cto/

• http://www.brixtonspa.com/Career/The_Role_of_the_CTO_4Models.pdf
 Technical Role, But!
• Responsible for success of the company, not
technology
– Strategy, Technical & Business
– Participate in Sales
– Partnership Discussions
– Fund Raising
– Build vs. Buy Decisions
 Your SkillZ
• Technical
• Process / Operational
• Leadership / Management
• Executive
 1. Technical Skills *
• Expert-Level
–CS 101 – Data Structures, Algorithms
–Chosen field of technology (Ruby, .NET, Java, Python, PHP)
–OO / Functional Design
–Performance Tradeoffs
–UI Technologies (HTML, CSS, Ajax Libraries)
–Design & Software Architecture
• Good General Understanding
–Security
–Persistence Options
–Cloud Architectures / Hosting
–Mobile Platforms
–Scaling
–Integration Options & Architectures
–Infrastructure & Systems Operations

• Evaluating Technologies & Products

* (Focus of CTO School Session 2)

 Helpful To Know
• UX & Usability
• Design Sense
• Product Marketing
• Metrics
• System Administration
 Special Tech Skills
• Enterprise Space & Architecture
• Facebook, OpenSocial, Web Platforms
• Payments / Subscriptions Technologies
• Content Management
• SEO
• Ad Platforms
• Special Algorithms & Technologies
• Hardware
 2. Dev Process Skills *
• Software Development Life Cycle
• Agile, Kanban, Lean, Scrum
• Source Control & Build Tools
• Issue Tracking
• Quality Assurance
• Security Processes
• Project Management
• Estimation

• * (Focus of CTO School Session 3)

 3. Leadership / Management Skills
• Depend on Company Stage / Size
– Lead Through Doing / Example
– Lead Through Others
– Lead By Vision
• Setting Technical Direction
• Hiring & Growing Teams
• Managing People, including Remote
• Mentoring & Growing People
• Motivating
• Public Speaking
• Writing
 4. Being Part of Executive Team
• Think in terms of the company, not technology
• Offer Technical Options
• Resource Planning
• Educate the other executives about
technology capabilities, processes, etc.
• Input on short and long-term business vision,
strategies and plans;
• Help define business priorities
 More on Executive Skills
• Review and influence the product road map,
• Review / provide input on some investor presentation
materials, business proposals
• Participate in new business, partnership or investor meetings
on a limited basis,
• Business practices that will help to derive greatest short-term
and long-term value from the technical team and other
resources.

• http://socalcto.blogspot.com/2007/12/acting-cto-role-in-
start-up.html
 Skills Conclusion
• Too much to know
– Make a plan for your own growth
• Different priorities compete with each other.
– ALL are important
– Difficult to make short-term vs. long-term tradeoffs
– Effective Time Management is essential.
• Make sure you know what’s most important for
you right now
 Links
• http://www.feld.com/wp/archives/2007/10/cto-vs-vp-engineering.html
• http://www.startuplessonslearned.com/2008/09/what-does-startup-cto-actually-do.html
• http://pmarca-archive.posterous.com/the-pmarca-guide-to-startups-part-8-hiring-ma
• http://www.joelonsoftware.com
• http://mitchellashley.typepad.com/the_converging_network/2007/10/cto-and-vp-engi.html
• http://www.bothsidesofthetable.com/2010/04/19/want-to-know-the-difference-between-a-cto-and-a
-vp-engineering/
• http://www.quora.com/Engineering-Management/What-are-the-most-important-qualities-in-a-great-
VP-of-Engineering-for-a-consumer-Web-business
• http://littletutorials.com/2008/07/07/success-as-technical-lead/
• http://stackoverflow.com/questions/833897/what-makes-a-good-technical-team-lead
• http://stackoverflow.com/questions/79896/what-else-does-one-need-on-top-of-programming-skills-to
-be-a-good-technical-lead
• http://stackoverflow.com/questions/465560/most-important-non-technical-skill-youve-acquired
• http://stackoverflow.com/questions/246585/what-is-the-most-important-thing-to-do-for-a-new-techni
cal-manager-or-lead
• http://codemonkeyism.com/startup-cto/
• http://www.allthingsdistributed.com/cto/
• http://www.amazon.com/CTO-Job-Manual-Leadership-Technology/dp/1587623676
• http://www.brixtonspa.com/Career/The_Role_of_the_CTO_4Models.pdf
• http://www.modelbenders.com/papers/CTOStrategy_SmithR.pdf