Software Lead Weekly
Issue #669, 19th September 2025
This Week's Favorite
How to Build Your First Forward Deployed Engineering Team
11 minutes read.
“Someone who sits at the customer site and fills the gap between what the product does and what the customer needs. […] Put an engineer as close as possible to the problem.” — Fills the gap. Not mapping it, documenting it, or (only) helping with adoption. These are Software Engineers, not PMs nor technical consultants: “If your FDE hasn’t built something in the last couple of weeks, it’s not FDE. […] autonomy is non-negotiable, they need to win. […] FDE is a product discovery loop, not an implementation services. […] You’re shipping results, not an install.” They need to immerse themselves there for a few weeks or months, not a “site visit” of Monday to Thursday to call it a day. And if the loop works well, solutions become repeatable abstractions that you can use, you’re on the right track: “If signals aren’t trending right and smells persist - revenue per FDE flatlines and custom work continues to accumulating - you may be running a service loop.” This is a viable model only if you’re selling at a seven-figure ACV contract and above, as this is an expensive operation to run.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
11 minutes read.
“Someone who sits at the customer site and fills the gap between what the product does and what the customer needs. […] Put an engineer as close as possible to the problem.” — Fills the gap. Not mapping it, documenting it, or (only) helping with adoption. These are Software Engineers, not PMs nor technical consultants: “If your FDE hasn’t built something in the last couple of weeks, it’s not FDE. […] autonomy is non-negotiable, they need to win. […] FDE is a product discovery loop, not an implementation services. […] You’re shipping results, not an install.” They need to immerse themselves there for a few weeks or months, not a “site visit” of Monday to Thursday to call it a day. And if the loop works well, solutions become repeatable abstractions that you can use, you’re on the right track: “If signals aren’t trending right and smells persist - revenue per FDE flatlines and custom work continues to accumulating - you may be running a service loop.” This is a viable model only if you’re selling at a seven-figure ACV contract and above, as this is an expensive operation to run.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Culture
Lovable, OpenAI, Nvidia
1 minutes read.
My humble effort to help you start the weekend with a smile on your face.
Read it later via Pocket or Instapaper.
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1 minutes read.
My humble effort to help you start the weekend with a smile on your face.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Evidence-Based GenAI DevEx
6 minutes read.
I love companies that seek to find the truth rather than continue and publish nonsense on LinkedIn and Twitter. You can learn a lot from CloudKitchen - their evaluation metrics, discussing what actually works, examining multiple dimensions to understand productivity (not just writing code), and finding ways to tackle more complex tasks, such as debugging (e.g., on-call incidents). We’ve gone through a very similar journey and reached similar conclusions at Forter, where I work, while optimizing for impact rather than empty claims. Share this post internally with your team and explore how you can encourage them to experiment further while advancing the business.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
6 minutes read.
I love companies that seek to find the truth rather than continue and publish nonsense on LinkedIn and Twitter. You can learn a lot from CloudKitchen - their evaluation metrics, discussing what actually works, examining multiple dimensions to understand productivity (not just writing code), and finding ways to tackle more complex tasks, such as debugging (e.g., on-call incidents). We’ve gone through a very similar journey and reached similar conclusions at Forter, where I work, while optimizing for impact rather than empty claims. Share this post internally with your team and explore how you can encourage them to experiment further while advancing the business.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Every Year You Should Double Your “TTAM”. Your True TAM.
4 minutes read.
Interesting insight that can help you understand how to lead a VC-backed company or to reason about the motivation and actions you see happening as an employee. Increasing TAM requires a lot of discipline to execute correctly, as it creates a lot of friction to educate your team on how to take a new offering to market and sell it. This is why most companies refrain from doing so in the first few years, as their focus is the only thing that keeps them alive.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
4 minutes read.
Interesting insight that can help you understand how to lead a VC-backed company or to reason about the motivation and actions you see happening as an employee. Increasing TAM requires a lot of discipline to execute correctly, as it creates a lot of friction to educate your team on how to take a new offering to market and sell it. This is why most companies refrain from doing so in the first few years, as their focus is the only thing that keeps them alive.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
The Hidden Trade-Offs of Fine-Grained Progressive Rollouts
4 minutes read.
You live and die by your observability stack. A fine-grained model assumes you have excellent capabilities to detect issues at a granularity that might not align with your release strategy (e.g., you roll out for a percentage of users but cannot segment them well in your observability stack to detect issues for that logic). Align your rollout strategy to match your MTTD & MTTR capabilities, assuming something fails in the rollout.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
4 minutes read.
You live and die by your observability stack. A fine-grained model assumes you have excellent capabilities to detect issues at a granularity that might not align with your release strategy (e.g., you roll out for a percentage of users but cannot segment them well in your observability stack to detect issues for that logic). Align your rollout strategy to match your MTTD & MTTR capabilities, assuming something fails in the rollout.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Peopleware
Being Good Isn’t Enough
4 minutes read.
“The less competent we are at something, the more likely we are to overestimate ourselves. It’s easy to think you’re working on what matters, or that you’re doing great technical work, but that might not be true. […] do it in the open. A common mistake is assuming work speaks for itself. It rarely does.” — Figuring out how to be incredibly effective in at least two out of the four dimensions (technical craftsmanship, product sense, project leadership, people leadership) can boost your career. Mastering all four and leading with Agency can make it a sustainable career that adjusts well to market needs. It’s never easy, as you need to grow faster than the company’s immediate needs to master these four dimensions.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
4 minutes read.
“The less competent we are at something, the more likely we are to overestimate ourselves. It’s easy to think you’re working on what matters, or that you’re doing great technical work, but that might not be true. […] do it in the open. A common mistake is assuming work speaks for itself. It rarely does.” — Figuring out how to be incredibly effective in at least two out of the four dimensions (technical craftsmanship, product sense, project leadership, people leadership) can boost your career. Mastering all four and leading with Agency can make it a sustainable career that adjusts well to market needs. It’s never easy, as you need to grow faster than the company’s immediate needs to master these four dimensions.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
You're Definitely Going to Be a Manager Now
4 minutes read.
“The old boundary lines are blurring. Just as we’ll see fewer “pure managers”, we’ll also see fewer “pure ICs”. Instead, more people will live in the messy middle: sometimes executing, sometimes designing processes, sometimes coordinating.“ — I think it will move outside of your primary discipline as well, getting ICs to develop taste not only in their immediate realm of expertise (e.g. software engineering) but also what should be built and how to verify it with customers or users. Mental capacity (and pressure) will increase further until it reaches a new equilibrium, at which point tools will bring it back down.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
4 minutes read.
“The old boundary lines are blurring. Just as we’ll see fewer “pure managers”, we’ll also see fewer “pure ICs”. Instead, more people will live in the messy middle: sometimes executing, sometimes designing processes, sometimes coordinating.“ — I think it will move outside of your primary discipline as well, getting ICs to develop taste not only in their immediate realm of expertise (e.g. software engineering) but also what should be built and how to verify it with customers or users. Mental capacity (and pressure) will increase further until it reaches a new equilibrium, at which point tools will bring it back down.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Inspiring Tweets
@DmytroKrasun: Developers switch between coding agents every week like they were switching between JavaScript frameworks before. Ironically losing productivity gains because of the switch itself and talking about it.
- Oren
P.S. Can you share this email? I'd love for more people to experiment and improve their company's culture.
P.S. Can you share this email? I'd love for more people to experiment and improve their company's culture.