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The Startup CTO's Handbook

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Re: The Startup CTO's Handbook

#3
One way I try to get my head around things like this is to skip to a section I understand deeply and see what they said. Here, the claim is made:

Don't try to get a compliance certificate at the last minute. Preparing for and conducting an audit such as for PCI DSS or SOC 2 from start to finish is a lengthy process, ranging from six to twelve months for most startups. Starting early and maintaining compliance is cheaper than starting late and doing rework.

This is basically the opposite of the advice I would give a startup. SOC2 attestations in particular are easy to get, and are a waste of money to obtain preemptively before there are purchase orders on the line for them.

There are things you should start doing early that lay the groundwork for attestations, but you should be doing them anyways, even if you never plan to get a SOC2 (and if a big-ticket customer never demands it, you shouldn't SOC2). That's stuff like setting up single sign-on and having protected git branches; simple best practices.

Anyone else want to spot check other parts of this document? I wouldn't feel qualified to challenge most of it.

Re: The Startup CTO's Handbook

#4
post #3

One way I try to get my head around things like this is to skip to a section I understand deeply and see what they said. Here, the claim is made: Don't try to get a compliance certificate at the last minute. Preparing for and conducting an audit such as for PCI DSS or SOC 2 from start to finish is a lengthy process, ranging from six to twelve months for most startups. Starting early and maintaining compliance is chea…

Yeah, in my experience, most companies who are going to 1) do business with early stage startups and 2) want SOC2 report, are going to be totally fine with writing “startup X will get their SOC2 type 1 in the next six months” into the contract and moving forward, so long as someone technical can get on the phone with their IT people convince them you are reasonably competent.

Re: The Startup CTO's Handbook

#5
post #3

One way I try to get my head around things like this is to skip to a section I understand deeply and see what they said. Here, the claim is made: Don't try to get a compliance certificate at the last minute. Preparing for and conducting an audit such as for PCI DSS or SOC 2 from start to finish is a lengthy process, ranging from six to twelve months for most startups. Starting early and maintaining compliance is chea…

Great approach. I ctrl-F'd for databases, good info there generally. The only thing that gave me pause: a startup doesn't need to focus on SQL vs. NoSQL in 2025 with such good json support in the most popular SQL databases. Just use PostgreSQL or MySQL -- whichever your engineers have more experience with -- use CloudSQL or RDS which will take care of the hard stuff like backups and replication for you, use read replicas for BI with a good visualization tool, you'll be good with that for a good while before you need to fork over 5/6 figures for Snowflake or anything else.

Re: The Startup CTO's Handbook

#6
post #3

One way I try to get my head around things like this is to skip to a section I understand deeply and see what they said. Here, the claim is made: Don't try to get a compliance certificate at the last minute. Preparing for and conducting an audit such as for PCI DSS or SOC 2 from start to finish is a lengthy process, ranging from six to twelve months for most startups. Starting early and maintaining compliance is chea…

Made an account just to say that I respectfully disagree solely when it comes to accounting and supply chain processes in an enterprise ERP. Unwinding un-auditable processes costs so much f’ing time and money while the business still has to run that I’ve found it to be cheaper and better to be auditable from day 1, in this one specific instance.

Re: The Startup CTO's Handbook

#7
Has anyone worked in a "two crews" system where there wasn't resentment? Or where people didn't want to naturally migrate to the "future crew".

I like the idea of this on paper. I have a hard time believing it can work in practice. The closest I've seen are library teams that build some service (say a design system + components) that other teams utilize.

Re: The Startup CTO's Handbook

#8
post #6
post #3

One way I try to get my head around things like this is to skip to a section I understand deeply and see what they said. Here, the claim is made: Don't try to get a compliance certificate at the last minute. Preparing for and conducting an audit such as for PCI DSS or SOC 2 from start to finish is a lengthy process, ranging from six to twelve months for most startups. Starting early and maintaining compliance is chea…

Made an account just to say that I respectfully disagree solely when it comes to accounting and supply chain processes in an enterprise ERP. Unwinding un-auditable processes costs so much f’ing time and money while the business still has to run that I’ve found it to be cheaper and better to be auditable from day 1, in this one specific instance.

I built one of the Trade Promotion Management platforms used in the NA market, and couldn't agree more. It's a nightmare trying to be auditable if you didn't think about it from the start.

Re: The Startup CTO's Handbook

#9
post #3

One way I try to get my head around things like this is to skip to a section I understand deeply and see what they said. Here, the claim is made: Don't try to get a compliance certificate at the last minute. Preparing for and conducting an audit such as for PCI DSS or SOC 2 from start to finish is a lengthy process, ranging from six to twelve months for most startups. Starting early and maintaining compliance is chea…

Do you know of a good resource which describes these simple best practices?

Re: The Startup CTO's Handbook

#10
post #3

One way I try to get my head around things like this is to skip to a section I understand deeply and see what they said. Here, the claim is made: Don't try to get a compliance certificate at the last minute. Preparing for and conducting an audit such as for PCI DSS or SOC 2 from start to finish is a lengthy process, ranging from six to twelve months for most startups. Starting early and maintaining compliance is chea…

Great approach. I ctrl-F'd for databases, good info there generally. The only thing that gave me pause: a startup doesn't need to focus on SQL vs. NoSQL in 2025 with such good json support in the most popular SQL databases. Just use PostgreSQL or MySQL -- whichever your engineers have more experience with -- use CloudSQL or RDS which will take care of the hard stuff like backups and replication for you, use read repl…

I was just commenting to a colleague recently about the significant improvements RDBMS have gotten for json support over the last decade. For instance, keys below the first level in Postgres jsonb fields were not indexable around a decade ago. Now you can do GIN index and other options that are rather sophisticated.
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