NYC CTO School S1 T1 What is CTO?

NextNY CTO SchoolFall 2010

Session 1 – What is CTO

Before We Start

Your Mileage May VaryFor 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-between-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-g

reat-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-s

kills-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-

technical-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