Modern Staff Engineering at a Startup

Presented at DevOpsDays in Birmingham, AL - August 21, 2024.

DevOps is all about breaking down barriers to a fast flow of value to customers. This fast flow is especially important at a startup, where every day is a precious race to create revenue faster than the runway drys up!

In this talk, I describe my first year in my role as Senior Staff Software Engineer at the NYC startup Smartrr, providing subscriptions as a service to Shopify brands. I share what I have learned about what makes working at a startup different from a larger organization and how I have adapted the concepts of DevOps, Staff Engineering and Platform Engineering to this environment. I also share examples of my work and how these concepts have supported my work.

I argue that DevOps is very relevant at a Startup and hope you agree after my talk.

Transcript

1. Modern Staff Engineering at a Startup a conference talk by Chad McElligott
2. DevOps Staff Engineering Platform Engineering Do apply at a Startup? { }
3. Hi, I’m Chad McElligott Senior Staff Engineer @ Smartrr • Subscriptions & Loyalty for Shopify Brands • Based in New York City • 18 in Product & Engineering • Series A Startup
4. DevOps Staff Engineering Platform Engineering What do these things really mean? { }
5. { About DevOps, Platform Engineering, & Staff Engineering } DevOps is…
6. { About DevOps, Platform Engineering, & Staff Engineering } • A mentality of collaboration • AND the automation of toil • AND Embracing modern tooling and techniques … to sustain a fast flow of value to customers. DevOps is…
7. { About DevOps, Platform Engineering, & Staff Engineering } my 2023 talk Platform Engineering is…
8. { About DevOps, Platform Engineering, & Staff Engineering } • A technique for reducing cognitive load on developers • Engineering Velocity 🤝 System Stability • Investing in the developer experience my 2023 talk Platform Engineering is… Engineering Enablement podcast
9. { About DevOps, Platform Engineering, & Staff Engineering } • Servant leadership for software engineering • Group or Organization-wide responsibility and impact • A partner to managers, directors, or VPs Staff Engineering is… Staff Engineer book
10. What’s different about a Startup, anyway?
11. { Cultural Qualities of a Startup } There is no time to waste
12. There is no time to waste { Cultural Qualities of a Startup } We all wear many hats
13. { Cultural Qualities of a Startup } There is no time to waste We all wear many hats
14. DevOps Staff Engineering Platform Engineering How does Startup Culture shape { }?
15. { DevOps, Platform Engineering, & Staff Engineering at a Startup } • Alter processes to fit your tools, not the other way around DevOps at a Startup
16. { DevOps, Platform Engineering, & Staff Engineering at a Startup } • Alter processes to fit your tools, not the other way around • Avoid as much custom tooling as possible DevOps at a Startup Martin Fowler’s post
17. { DevOps, Platform Engineering, & Staff Engineering at a Startup } • Alter processes to fit your tools, not the other way around • Avoid as much custom tooling as possible • Choose boring technology DevOps at a Startup Martin Fowler’s post Dan McKinley’s talk
18. { DevOps, Platform Engineering, & Staff Engineering at a Startup } Platform Engineering at a Startup Engineering Unblocked podcast
19. { DevOps, Platform Engineering, & Staff Engineering at a Startup } • Expect this to be a part-time hat Platform Engineering at a Startup Engineering Unblocked podcast
20. { DevOps, Platform Engineering, & Staff Engineering at a Startup } • Expect this to be a part-time hat • You’ll want to work in small batches - There’s no time for long projects! Platform Engineering at a Startup Engineering Unblocked podcast
21. { DevOps, Platform Engineering, & Staff Engineering at a Startup } • Expect this to be a part-time hat • You’ll want to work in small batches - There’s no time for long projects! • You’ll be blazing new trails, so choose your work wisely Platform Engineering at a Startup Engineering Unblocked podcast
22. { DevOps, Platform Engineering, & Staff Engineering at a Startup } Staff Engineering at a Startup
23. { DevOps, Platform Engineering, & Staff Engineering at a Startup } • Effective execution > navigating internal dynamics Staff Engineering at a Startup
24. { DevOps, Platform Engineering, & Staff Engineering at a Startup } • Effective execution > navigating internal dynamics • You’ll move between the “Staff archetypes” Staff Engineering at a Startup
25. { DevOps, Platform Engineering, & Staff Engineering at a Startup } • Effective execution > navigating internal dynamics • You’ll move between the “Staff archetypes” • Mentorship and Sponsorship will be key skills Staff Engineering at a Startup
26. Modern Staff Engineering Applied Stories from my 1st year at Smartrr
27. How I helped remove the merge freeze for better DevEx Story 1 of 2
28. { How I helped remove the merge freeze for better DevEx } Image credit: https://www.youtube.com/watch?v=6IoXFkfnYzE
29. { How I helped remove the merge freeze for better DevEx } • Slow to manually regression test • Changes frequently resulted in regressions • Merge freezes led to merge conflicts Quality Assurance Challenges
30. Company Objective: Enhance Smartrr’s Quality Project: Automate Manual Regression Test Suite My Task: Provision a new integrated testing environment The context of my first task { How I helped remove the merge freeze for better DevEx }
31. { How I helped remove the merge freeze for better DevEx } Simplified Smartrr Architecture
32. { How I helped remove the merge freeze for better DevEx } • Co-located the infrastructure with the application code Key Infrastructure Choices
33. { How I helped remove the merge freeze for better DevEx } • Co-located the infrastructure with the application code • Built Terraform for all environments, using variables for differences Key Infrastructure Choices
34. { How I helped remove the merge freeze for better DevEx } • Co-located the infrastructure with the application code • Built Terraform for all environments, using variables for differences • Simplified the CI/CD Key Infrastructure Choices
35. { How I helped remove the merge freeze for better DevEx } • Co-located the infrastructure with the application code • Built Terraform for all environments, using variables for differences • Simplified the CI/CD • Moved secrets to a proper secret store Key Infrastructure Choices
36. { How I helped remove the merge freeze for better DevEx } • Stop using Kubernetes for such a small application Out of Scope
37. { How I helped remove the merge freeze for better DevEx } • Stop using Kubernetes for such a small application • Automate terraform apply Out of Scope
38. { How I helped remove the merge freeze for better DevEx } • Stop using Kubernetes for such a small application • Automate terraform apply • Using a Kubernetes-native secrets manager Out of Scope
39. { How I helped remove the merge freeze for better DevEx }
40. { How I helped remove the merge freeze for better DevEx }
41. { How I helped remove the merge freeze for better DevEx }
42. DevOps Staff Engineering Platform Engineering How did { } apply in this story? { How I helped remove the merge freeze for better DevEx }
43. I applied • Seeking clarification across the company • Leading with intent • Assuming a “tech lead” archetype • Addressing larger goals in scope of the task { How I helped remove the merge freeze for better DevEx } Staff Engineering by…
44. I applied • Fully managing our infrastructure with Terraform • Choosing to walk away from some nice-to-haves { How I helped remove the merge freeze for better DevEx } Platform Engineering by…
45. • Leveraging Infrastructure as Code for consistency • Improving the release process once the tools were in place • Introducing RFCs for inclusive decision making { How I helped remove the merge freeze for better DevEx } I applied DevOps by…
46. { How I helped remove the merge freeze for better DevEx }
47. Iterating towards a productive engineering process Story 2 of 2
48. { Iterating toward a productive engineering process } Image credit: https://productivitymatters.com.au/wellbeing/occupational-burnout-its-real/
49. { Iterating toward a productive engineering process } agile all the things! • Draft proposals of changes • Frame changes as “experiments” • Make goals clear to all • Use retrospectives to reflect Image credit: https://hyperboleandahalf.blogspot.com/2010/06/this-is-why-ill-never-be-adult.html
50. { Iterating toward a productive engineering process } Experiment 󰳘 Short-lived Feature Teams • Goal - Build a sense of responsibility • Change - Short-lived full-stack feature teams • Outcome - Mixed. Has evolved to our squad model
51. { Iterating toward a productive engineering process } Experiment 󰳘 Epic Kickoff Documents • Goal - Clear communication when starting a project • Change - New meeting with a templated agenda • Outcome - Success! Value-packed discussions This is the doc, if you’re curious
52. { Iterating toward a productive engineering process } Experiment 󰳘 Group Code Review • Goal - Faster lead times; Encourage collaboration • Change - New twice-weekly open huddle for code review • Outcome - Success across the board ✨
53. DevOps Staff Engineering Platform Engineering How did { } apply in this story? { Iterating toward a productive engineering process }
54. I applied Staff Engineering by… { Iterating toward a productive engineering process } • Filling a void in process leadership • Empowering teams to shape their own processes • modeling desired behavior
55. I applied Understanding that process is a part of your platform Platform Engineering by… { Iterating toward a productive engineering process }
56. Leveraging the L in CALMS. Lean I applied DevOps by… { Iterating toward a productive engineering process }
57. DevOps Staff Engineering Platform Engineering { } + Startup ❤❤❤❤❤❤❤❤
58. Thank you! My blog My LinkedIn