Adventures in Enterprise

Lessons Learned
Promoting DevOps
in a Legacy Organization

Steve Desmond


DevOpsDays PDX

DevOpsDays Fued

What is Ithaca known for?

Gorges 54
Cornell 39
Road Trip   7


  • Culture
  • Automation
  • Measurement
  • Sharing


Software used to satisfy the needs of an organization rather than individual users
  • Payroll / HR systems
  • Classroom / lab computers
  • On-Campus LAN / Wi-Fi


  • On-premises datacenters
  • Physical servers
  • Weekend downtime
  • Project-centric planning
  • Traditional org structure

Story Time


Part 1

Do Not Go In
With Guns Blazing

Big Orgs Move Slow

TypeScript approval at Google


  • Stability over innovation
  • Control change vs embrace it
  • Physical scaling limitations
  • Project-centric planning

Software is not a Building

Don't construct them the same way


  • Filesystem I/O
  • LDAP management
  • HTTP connections

Be Prepared
For More Resistance
Than You Can Imagine

Assume Awesomeness

Lead By Example

"Be the CAMS model!"

Don't Rock The Boat

(too much)

(or do)

Team Dynamics Are Paramount

Part 2

Celebrate Your Small Wins

Recognize Your Victories

Manifesto for Agile Software Development

We are uncovering better ways of developing software by doing it and helping others do it.

Through this work we have come to value:

  • Individuals and interactions over processes and tools
  • Working software over comprehensive documentation
  • Customer collaboration over contract negotiation
  • Responding to change over following a plan

That is, while there is value in the items on the right, we value the items on the left more.

Small Controlled Experiments




Decouple from your Enterprise Systems

Graduate Application

Extend via Configuration,
Don't Fork Vendor Code

Private Social Network

Look for Low-Hanging Fruit

Student Self-Service

Lead Times

  • ERP: 2-7 days
  • Web: 5-20 minutes


You (as an individual)
Can't Change Culture

Part 3

Maybe DevOps Isn't Right
For Every Organization

Part 3

Maybe DevOps Isn't Right
For Every Organization

Part 3

Maybe It's Not The Right Time
For DevOps Yet

Part 3

Maybe It's Not The Right Time
For DevOps Yet

You (as an individual)
Can't Change Culture

  • Spark change in others
  • Lead by example (be the CAMS model!)
  • Be patient


  • Low-cost
  • Low-risk
  • Goal = Kaizen

Decouple, Decouple, Decouple

  • UI from Database
  • Front-End from Back-Office
  • Custom Features from Vendor Software

Guide Your Team
On A Nature Hike

Don't Just Drag Them
Through The Woods

High Fives

Steve Desmond Software Development