SAMPLE WORK
Writing that earns the next conversation
Five speculative pieces written in the voice of the executive, not around them. Each one stakes a position and defends it.
Series B SaaS founder — AI pricing pressure
"The SaaS companies panicking about AI pricing pressure aren't facing a business model problem. They're facing a value delivery problem they've been hiding behind subscriptions for years."
It will definitely be a challenge for some, as the very DNA of their offering is built around what they’ve been able to get away with for some time; a per seat charge or monthly charge for their software, and it has been up to the user to extract the value proposition. While many companies track DAUs, and MAUs, (the smart ones,) there are many that are only concerned about the number of monthly subscriptions to their platform.
AI has fundamentally changed that mindset.
AI has challenged the traditional model pushing SaaS companies towards demonstrating the value of their offering, and what they’re actually delivering. Essentially, moving towards a transactional approach. The client pays for the value they receive when they actually receive it. While not a novel concept, it’s one that has suddenly gripped SaaS companies with fear.
Why?
Because their offering had questionable value to begin with. It doesn’t mean their idea was wrong, but their execution of it has been lackluster all this time, and clients simply treated it as that’s just the way it is with SaaS software. AI has brought all of that into the open and made it front and center. No more hiding behind the application.
Most of you already know which category you're in. The question is whether you're going to act on that before your customers do.
VP of Product — platform consolidation
"Everyone is selling platform consolidation right now. Almost nobody is solving the actual problem. ‘Single source of truth’ has become an oxymoron in digital marketing; promised endlessly, delivered almost never."
There is no doubt clients have always wanted one clear view of their marketing ROI. AI is finally making it impossible to keep pretending that's too hard to deliver by putting substantial pressure on firms to (finally) have offerings in a unified manner, as pricing models move to value based and not seat based.
This means taking often siloed, separate, legacy platforms, consolidating them into one, and delivering on those results to demonstrate the true ROI to the client.
Sounds expensive…and it will be. It’s also not the correct approach.
This isn’t a platform consolidation problem, as it’s masquerading as. It’s a data problem. Of course, you can make the argument that disparate systems need to be made into one behemoth platform to fulfill this promise, but that’s not necessary. Delivering and consolidating your data is.
The companies getting this right are not building bigger platforms. They are building better data products, with clear lineage, governance, and API layers that let every existing platform speak the same language, enabling proper data sharing across platforms, to internal users, and SMB clients alike.
How you actually build that unified data view without a $4M platform rebuild, that’s for the next discussion.
CMO — counterintuitive take on SMB retention
"Deliberately degrading your services to unprofitable SMB segments to accelerate their churn so you can redeploy those resources faster sounds like madness, but hear me out."
Digital marketing to SMBs takes a substantial amount of time, resources and above all, expenses to cultivate, on-board, and maintain. Many of those businesses, in very high numbers, will not be the client you originally took on. It’s the nature of SMBs that they themselves are in a high churn environment. This could be due to the SMB changing their business model and going in a different direction, being acquired, or ceasing to exist.
That puts you, the digital marketer, in an uncomfortable position, as you pour money and effort into (likely) 80% of your accounts that are doomed one way or another to not deliver you value. Your other 20% of your accounts that are profitable, and do deliver value, are subsidizing your business so you can pursue the other 80%.
What should you do instead?
Take all of that energy, that time, that expense, and improve your platforms and systems. Build tiered service models. Automate everything touching the bottom half of your client base. Put your best people and your product investment where the LTV justifies it. That’s the key to your overall success, improving your SaaS margins, and keeping your sanity in check.
The companies that figure this out first will not just improve their margins. They’ll be the ones still standing when the SMB market consolidates around platforms that actually deliver measurable value. The ones still chasing the 80% will not.
Ready to put your name on something worth reading?
Let's talk about what you're working on.
Start a conversation
Signal Copy • signalcopy.co • Dan Gesshel • Los Angeles • dangesshel@gmail.com
CTO — cloud migration post-mortem on what lift and shift actually costs you
"We migrated our platform to the cloud, and now it moves like sludge, despite everyone telling us the opposite. Here’s what we got wrong."
There was complete alignment throughout the organization and from our partners. The drumbeat from the CEO and the Board was loud and clear; make a plan and execute. A seemingly simple (and cost-effective) request. The problem is the “lift and shift” methodology that all cloud providers sell makes it sound like something straightforward and easy to do.
Yes, we took into account the obvious areas that we would need to fundamentally change, and our teams worked hard at re-architecting our connections from our network topology. We spent a substantial effort ensuring that the application and databases all could be fully migrated and operational. We configured and validated our new cloud environment. We ran countless QA checks throughout, and everything worked perfectly. The problem wasn’t the migration. It was what we migrated.
What no one examined was the actual application architecture. We discovered there were excessive queries causing database chattiness inherent in design, the existing architecture was highly inefficient for a cloud native environment, and the entire setup was built for on-prem servers that had dedicated drives sitting next to each other in our server room, not in some data center across the region. We had never designed the platform to need to move to managed cloud services, have microservices architecture, or edge caching.
We should have asked harder questions, not just “should we move it” but “should we move it as is.” Prior to the migration, deciding to rebuild the entire platform in a cloud-native environment would’ve properly prepared us for the entire initiative and set accurate expectations on costs and timeline. If you’re planning on migrating to the cloud, audit your complete architecture before doing the migration, and be up-front about the costs directly with your board and leadership team.
Getting stuck burning out your staff doing a rebuild of a platform you just re-engineered a year ago is not what you want to do.
VP of Product — what a cloud migration mandate actually costs the product org
"We did a cloud migration from one major provider to another for all of our products and platforms, but the true product costs and impacts were never accounted for. Here’s what we absorbed."
The entire enterprise was mandated to shift all of our systems to another cloud provider for cost-cutting purposes. The work would be carried out in parallel to other product initiatives and no additional headcount approved, with a completion date prior to the end of the fiscal year. Immediately that impacted our multi-year roadmaps, cutting our delivery time for new features and enhancements in half, but that was only part of the story.
As engineering teams were pulled off of other projects, it began to stall initiatives that were critical to sales and other parts of the organization. Some were built considerably slower than planned, some were never built at all. The opportunity cost was becoming real.
To mitigate some of this we had to devise work on a parallel path, creating multiple code bases in the process; some work on the existing system, and some work on the new one, making it all look like a unified application. This of course accrued migration debt, forcing the teams at a later stage to go back to the products again, and re-do work that had just been done a few months earlier.
What product leaders need to demand before a migration mandate is put into place is a complete LOE assessment, and not just by the engineering and devops teams. Modeling out the impacts across roadmaps, understanding the opportunity cost, the impact on staff throughout the organization. Product leaders need to be explicit with their analysis and assessments, attributing them directly to KPIs and translating everything into dollars. Above all make sure what you’re doing is transparent, so leadership can understand the ramifications of their decisions, and prevent this from happening again in the future.
Doing this upfront will help leadership make better decisions on mandates like this, without burning out half the organization in the process.
Series B SaaS founder — AI pricing pressure
"The SaaS companies panicking about AI pricing pressure aren't facing a business model problem. They're facing a value delivery problem they've been hiding behind subscriptions for years."
It will definitely be a challenge for some, as the very DNA of their offering is built around what they’ve been able to get away with for some time; a per seat charge or monthly charge for their software, and it has been up to the user to extract the value proposition. While many companies track DAUs, and MAUs, (the smart ones,) there are many that are only concerned about the number of monthly subscriptions to their platform.
AI has fundamentally changed that mindset.
AI has challenged the traditional model pushing SaaS companies towards demonstrating the value of their offering, and what they’re actually delivering. Essentially, moving towards a transactional approach. The client pays for the value they receive when they actually receive it. While not a novel concept, it’s one that has suddenly gripped SaaS companies with fear.
Why?
Because their offering had questionable value to begin with. It doesn’t mean their idea was wrong, but their execution of it has been lackluster all this time, and clients simply treated it as that’s just the way it is with SaaS software. AI has brought all of that into the open and made it front and center. No more hiding behind the application.
Most of you already know which category you're in. The question is whether you're going to act on that before your customers do.
VP of Product — platform consolidation
"Everyone is selling platform consolidation right now. Almost nobody is solving the actual problem. ‘Single source of truth’ has become an oxymoron in digital marketing; promised endlessly, delivered almost never."
There is no doubt clients have always wanted one clear view of their marketing ROI. AI is finally making it impossible to keep pretending that's too hard to deliver by putting substantial pressure on firms to (finally) have offerings in a unified manner, as pricing models move to value based and not seat based.
This means taking often siloed, separate, legacy platforms, consolidating them into one, and delivering on those results to demonstrate the true ROI to the client.
Sounds expensive…and it will be. It’s also not the correct approach.
This isn’t a platform consolidation problem, as it’s masquerading as. It’s a data problem. Of course, you can make the argument that disparate systems need to be made into one behemoth platform to fulfill this promise, but that’s not necessary. Delivering and consolidating your data is.
The companies getting this right are not building bigger platforms. They are building better data products, with clear lineage, governance, and API layers that let every existing platform speak the same language, enabling proper data sharing across platforms, to internal users, and SMB clients alike.
How you actually build that unified data view without a $4M platform rebuild, that’s for the next discussion.
CMO — counterintuitive take on SMB retention
"Deliberately degrading your services to unprofitable SMB segments to accelerate their churn so you can redeploy those resources faster sounds like madness, but hear me out."
Digital marketing to SMBs takes a substantial amount of time, resources and above all, expenses to cultivate, on-board, and maintain. Many of those businesses, in very high numbers, will not be the client you originally took on. It’s the nature of SMBs that they themselves are in a high churn environment. This could be due to the SMB changing their business model and going in a different direction, being acquired, or ceasing to exist.
That puts you, the digital marketer, in an uncomfortable position, as you pour money and effort into (likely) 80% of your accounts that are doomed one way or another to not deliver you value. Your other 20% of your accounts that are profitable, and do deliver value, are subsidizing your business so you can pursue the other 80%.
What should you do instead?
Take all of that energy, that time, that expense, and improve your platforms and systems. Build tiered service models. Automate everything touching the bottom half of your client base. Put your best people and your product investment where the LTV justifies it. That’s the key to your overall success, improving your SaaS margins, and keeping your sanity in check.
The companies that figure this out first will not just improve their margins. They’ll be the ones still standing when the SMB market consolidates around platforms that actually deliver measurable value. The ones still chasing the 80% will not.
CTO — cloud migration post-mortem on what lift and shift actually costs you
"We migrated our platform to the cloud, and now it moves like sludge, despite everyone telling us the opposite. Here’s what we got wrong."
There was complete alignment throughout the organization and from our partners. The drumbeat from the CEO and the Board was loud and clear; make a plan and execute. A seemingly simple (and cost-effective) request. The problem is the “lift and shift” methodology that all cloud providers sell makes it sound like something straightforward and easy to do.
Yes, we took into account the obvious areas that we would need to fundamentally change, and our teams worked hard at re-architecting our connections from our network topology. We spent a substantial effort ensuring that the application and databases all could be fully migrated and operational. We configured and validated our new cloud environment. We ran countless QA checks throughout, and everything worked perfectly. The problem wasn’t the migration. It was what we migrated.
What no one examined was the actual application architecture. We discovered there were excessive queries causing database chattiness inherent in design, the existing architecture was highly inefficient for a cloud native environment, and the entire setup was built for on-prem servers that had dedicated drives sitting next to each other in our server room, not in some data center across the region. We had never designed the platform to need to move to managed cloud services, have microservices architecture, or edge caching.
We should have asked harder questions, not just “should we move it” but “should we move it as is.” Prior to the migration, deciding to rebuild the entire platform in a cloud-native environment would’ve properly prepared us for the entire initiative and set accurate expectations on costs and timeline. If you’re planning on migrating to the cloud, audit your complete architecture before doing the migration, and be up-front about the costs directly with your board and leadership team.
Getting stuck burning out your staff doing a rebuild of a platform you just re-engineered a year ago is not what you want to do.
VP of Product — what a cloud migration mandate actually costs the product org
"We did a cloud migration from one major provider to another for all of our products and platforms, but the true product costs and impacts were never accounted for. Here’s what we absorbed."
The entire enterprise was mandated to shift all of our systems to another cloud provider for cost-cutting purposes. The work would be carried out in parallel to other product initiatives and no additional headcount approved, with a completion date prior to the end of the fiscal year. Immediately that impacted our multi-year roadmaps, cutting our delivery time for new features and enhancements in half, but that was only part of the story.
As engineering teams were pulled off of other projects, it began to stall initiatives that were critical to sales and other parts of the organization. Some were built considerably slower than planned, some were never built at all. The opportunity cost was becoming real.
To mitigate some of this we had to devise work on a parallel path, creating multiple code bases in the process; some work on the existing system, and some work on the new one, making it all look like a unified application. This of course accrued migration debt, forcing the teams at a later stage to go back to the products again, and re-do work that had just been done a few months earlier.
What product leaders need to demand before a migration mandate is put into place is a complete LOE assessment, and not just by the engineering and devops teams. Modeling out the impacts across roadmaps, understanding the opportunity cost, the impact on staff throughout the organization. Product leaders need to be explicit with their analysis and assessments, attributing them directly to KPIs and translating everything into dollars. Above all make sure what you’re doing is transparent, so leadership can understand the ramifications of their decisions, and prevent this from happening again in the future.
Doing this upfront will help leadership make better decisions on mandates like this, without burning out half the organization in the process.
Ready to put your name on something worth reading?
Let's talk about what you're working on.
Start a conversation
Signal Copy • signalcopy.co • Dan Gesshel • Los Angeles • dangesshel@gmail.com