Embracing Culture, Sharing, and Systems from Employee 1. Reference Article: https://rickmanelius.com/article/employee-1-and-beyond-system-set-checklist Presented at the Boulder DevOps Presentation Meetup on 11/2019

1. A DevOps Checklist for Startups
Embracing Culture, Sharing, and Systems from Employee 1
Boulder DevOps Meetup: 2019-11-18
@rickmanelius

2. 1. Knowledge sharing in a company or team of one is trivial:
○ YOUR head
○ YOUR inbox
○ YOUR sms messages
○ YOUR laptop
○ YOUR standard operating procedures
○ YOUR customer or client relationships
○ YOUR office
○ YOUR whiteboard
○ YOUR YOUR YOUR….
2. This strategy optimizes for short-term speed; long-term pain.
3. DevOps: silos stunt successful growth or performance of an org chart.
4. New people are unable to achieve autonomy & mastery/understand purpose.
The Problem

3. Solutions are Not Rocket Science, Yet Uncommon :(
● “It’ll only take 5 minutes”
● Actual Wait Times:
○ 1-hour at 90% utilization
○ 1-day at 99% utilization
● “It’ll only take an hour”
● Actual Wait Times:
○ 1 days at 90% utilization
○ 2.5 weeks at 99% utilization!!!
Source: The Phoenix Project

4. The Paradox: Need Space to Generate More Space
The following scenario plays out over and over again.
1. Top performer is over utilized and raises a hand for help.
2. Company moves quickly to hire or reallocate resources.
3. Top performer can’t stop everything and spend 25% of their time onboarding.
4. New hire either quits or remains underutilized.
If you’re top resources are near/over 100% utilization, #3-4 will be impossible.
● This checklist was my way to continually un-bottleneck myself.
● A few 1-3% changes in utilization time lead to massive changes in wait time.
● Reinvest new space again and again before utilization goes to 100%.

5. Who Am I? (for Context)
● BS & PhD in Material Science and Engineering
○ Lots of computation and numerical analysis.
● College: Track & Field Coach & Resident Advisor
● Backend Developer
● Product Development
● Solutions Architect
● Director of Ops
● COO of newmedia (Web agency)
● CPO of DRUD Technology (DevOps for Web Devs)
● CTO of Contact Mapping (Personal CRM)
● Techstars Mentor w/The Nature Conservancy

6. Goals
1. Leverage DevOps principles, patterns, benefits organization wide.
2. Establish this substrate and culture from person 1 (new startup or team).
3. Provide specific examples and strategies that I’ve used over 5 companies.
Ultimately, inspire ideas that you can apply to your own situation (present/future).

7. Tech Startups Are Already Hard Enough...
● Burnout
● Bottlenecks (Book: The Goal / Theory of Constraints)
● Brents (Phoenix Project)
Which is why DevOps leaders like Gene Kim had the following mission:
“Our goal is to elevate the state of technology work, quantify the economic and
human costs associated with suboptimal IT performance, and to improve the lives
of one million IT professionals by 2017”

8. ● 6 early stage startups in 10 years.
● COO (growing agency w/two incubated startups from 8 to 60 people).
○ Bringing on new departments: design, sales, marketing, HR, accounting, support, etc.
Key Learnings:
● It’s not enough to break down the silo’s between “Dev” and “Ops”
● It’s about setting a template that allows expansion from 1 to 100 from Day 1.
... and I’ve been there.

9. ● CAMS
○ Culture
○ Automation
○ Measurement
○ Sharing
● Theory of Constraints
○ Local Optimizations Can Lead to Global Slowdown
○ An hour lost at the bottleneck is an hour lost for the entire company
● Silos
○ Exist anywhere information can not be readily accessed.
○ Digital: Individual email inboxes, files on a computer
○ Analog: Files, Whiteboards, Watercooler Conversations.
○ Organic: Information in one’s brain and not another.
DevOps Crash Course

10. The Startup Silo Dilemma
● Constraints:
○ Finite Cash
○ Big ideas
○ Tremendous Uncertainty
○ Time is of the Essence
● So it’s almost certain to fall into the traps of…
○ “It’s faster if I just do it myself”
○ “We have a small team so we don’t need to spend time documenting or communicating.”
● That’s a real Brent move.
○ Brent is always the hero (yay 10X engineer!) and the villain (nothing gets done without Brent).
● We need to instill ways of developing a culture of sharing.

11. Key Concepts and Mindsets
● You Want to Automate or Delegate Yourself Out of a Job
○ Otherwise, the org chart will never expand.
● You Want to Turn Data Silos Into Substrates & Switches
○ Information needs to easily grow where it’s supposed to be.
○ Information access needs to be easily granted or removed.
● You Want to Empower People to Self Serve
○ Limit at all costs the need to make bottlenecks a dependency.

12. Alright... Let’s Get To It! After Caveats...
● Your Mileage May Vary
● Patterns Are More Important Than Specific Tools
● Not All Examples Will Apply To Your Specific Situation
● Don’t Confuse Simple With Not Valuable.
○ A 1% change can result in a 50% decline in wait time (e.g. 99% vs 98% utilization)

13. The Checklist at a Glance
● Email + Calendar
● Document Management
● Project Management
● Customer Relationship Management (CRM)
● Secrets/Passwords
● Video/Audio Conferencing
● Chat/Messaging
● Legal
● Code
● OKRs (or Mission, Vision, Values, and/or Goals)
● Communication Norms

14. My Preferred Toolchain
● Email + Calendar (G Suite)
● Document Management (Google Drive)
● Project Management (JIRA)
● Customer Relationship Management (Pipedrive or Hubspot)
● Secrets/Passwords (1Password Team)
● Video/Audio Conferencing (Zoom)
● Chat/Messaging (Slack)
● Legal (Pandadocs for customers; Docusign for HR)
● Code (GitHub + the rest of the DevOps Toolchain)
● OKRs (Store with docs)
● Communication Norms (Store with docs and review during onboarding)

15. System Solution #1: Email Groups
● Even as the Founder/CEO, try to move communications to these areas.
○ accounts@yourcompany.com (and assign yourself to it).
○ billing@yourcompany.com (and assign yourself to it).
○ support@yourcompany.com (and assign yourself to it).
○ team@yourcompany.com (and assign to everyone in your G Suite account).
● Justifications:
○ At some point, you will want others to join you in these areas.
■ Billing => Accountant or CPA
■ Accounts => Another 1-2 root level admins.
■ Support => Any/all people understanding Tier 1-3 history.
○ You will not have to mass forward all emails each time OR get constant 1-off requests.
○ Hit by a bus or win the lotto! Need to have redundancy of access and password resets.
○ Can cc/bcc like crazy and keep a full history of a conversation.

16. System Solution #2: Team Drives
● G Suite has the concept of shared drives with top level users/permission.
● All new docs inherit access control.
● All docs are owned by the company (and don’t disappear if someone leaves).
● Can grant/remove entire sections at once vs per doc grants.
● Copied docs are created right in these folders.
● All docs are searchable.
● Can mount on your local machines if needed.
● Can pin in Slack Channels

17. System Solution #3: Team Vaults
● 1Password Team has the concept of multiple shared password vaults.
● All new secrets inherit access control.
● All secrets are owned by the company (& don’t disappear if someone leaves).
● Can grant/remove entire sections at once.
● Gets around 1-off sharing.
● Browser integration
● Can assist owners in knowing which passwords to rotate (and when).

18. System Solution #4: Slack Rooms
● Slack overload is a thing, so…
● Try to segment rooms as much as possible by context
○ Support
○ Testing
○ JIRA notifications (can mute/leave)
○ GitHub notifications (can mute/leave)
○ CI/CD notifications (can mute/leave)
○ Client X, Y, or Z
○ Project X, Y, or Z
● People only join what matters and that can change.
● Keep trying to find the sweet spot of quantity vs Signal/Noise

19. System Solution #5: CRM
● At some point, the inbox silo will become crushing.
● Most CRMs have a cc/bcc solution to easily connect communication activity.
● Can also connect to support and billing systems for a fuller picture.

20. And More...
● With so many communication options, a “norms” doc can help people
understand where different types of information should go.’
○ Allowing everyone to tuck information elsewhere results in data leaks and silos.
● Legal Docs
● Reference Guides
● No SMS policy (not company property or searchable or grantable).

21. Take Away Patterns
● Ideally at some point, someone will have your job or perform your activities.
● Information needs to be consistently placed where access can be granted.
● Different tools serve different contexts (e.g. real time chat vs long term
storage).
● Small changes can lead to massive changes at a bottleneck
● Small changes can allow the org chart to grow or perform more effectively.

22. Questions?
● Feel free to reach out to me at @rickmanelius (LinkedIn, Twitter, etc).