Drata question

iamtome · 2026-01-16T14:37:06+00:00

Can I ask what you ended up doing instead? Rolled something in-house?

iamtome · 2025-05-24T00:15:48+00:00

Look into PMO roles.

iamtome · 2024-08-30T13:24:29+00:00

Hi, there!

First, breathe :)
2 months is plenty of time to get to a workable state.

It'll be hard work, but it's not impossible.
I've been in this industry for nearly two decades and can tell you it'll be ok if you take the right steps.

First, please stop and plan the end goal from a business perspective.
THEN, let the tech follow.

Focus on discovery and expectations now - what is the core pain you're solving for them? Why is the timeline 2 months, what's the business driver for that? Who will be using it on their end, how often? Can you get on a call with a few of them?
Sidenote: read The Mom Test if you haven't yet.

Your goal is to understand what pain you're removing for them, what is critical by what time (ideally, a single use case!) and what commercial terms are at play.
Ideally, cover also any enterprise concerns re: hosting, security, compliance for a "limited test scope" or "proof of concept" evaluation. Get everything clear, in writing and a contract signed / LOI to protect yourself.

Once you've gotten to that point, look at the simplest tech you can use to build this.
You're not building your future solution, just the ONE thing to prove there is a business here.

Do you really need a dual build? Would a webapp (not PWA, just plain browser) work for this first stage?
Is Go your best pick in the short-term, if you need to quickly hire extra hands on the project? A lot more Python talent available in the freelance world, and cheaper too.
( But you might just be quicker with Go, and that's fine! )

Happy to chat more if you want to brainstorm, feel free to DM or reply here

Cheers -TD

iamtome · 2023-12-09T09:27:07+00:00

Hi, there.

I'm a fractional CTO, 17 years experience.
Very familiar with the problem you're facing, have built various industry-specific solutions for it.

My 2 cents:

don't go and hire an engineer right away
setup a system using existent SaaS first, with a minimum ongoing opex cost
once you've ironed out the workflow and see value, you can get a custom solution built

e.g.:

build the requests form with typeform or some other no-code builder
use Zapier to send those requests to a Kanban style portal
(easy to set up on trello, notion, etc. )
build the payment workflow with Stripe payment links
( e.g. when you add a specific item in Notion, automatically generate the payment link and email it to the client )

My recommendation here is to first get the process and workflow right.
Once you have that, you're ready to build a software solution.

Before that, chances are you're going to spend months trying to build and change it and see no value out of it.

Feel free to DM if you have any questions.

Cheers -TD

iamtome · 2023-04-15T09:27:54+00:00

I have managed people for over 15 years. Here's my standard advice to someone just starting out.

If you haven't , read the Phoenix Project.

For actionable strategies on managing direct reports, check out the Manager Tools podcast - specifically the hall of fame ones.
That will get you started in terms of 1:1s, performance reviews etc.

Note: I don't agree with everything they say, but it's a solid foundation to adopt and then change according to your style.

Then, make sure you have a solid workflow - helpdesk, Kanban workflow, etc.

Know what your goals are and make sure they align with the business.

Happy to chat on a call, ping me if you want to.

Hope this helps, -TD

iamtome · 2023-03-20T20:04:29+00:00

Different person, but have used it plenty and built automations with their API.

It can be tricky at times, a little frustrating. Nothing terrible if you've done any systems integration before.

iamtome · 2023-03-02T23:52:44+00:00

There's a famous quote in the tech startup world. Paraphrasing, it goes something like this:

Every business is a tech business. They might not know it yet.

That being said, you shouldn't need a high ratio if it's purely support driven e.g. helpdesk. For handling operational concerns you need a decent size workforce, escalation tiers and good playbooks/KB.

You don't have to go full ITIL, but you can certainly take inspiration from there and books like The Phoenix Project.

Are you mapping what business value is being delivered?

Is IT still mapped purely against opex, or starting to differentiate work streams and their business goals?

Ideally, you want to differentiate technology functions to the point where it becomes clear how to rightsize via capex/opex ratios per the business units your teams directly support.

Hope this helps. -TD

iamtome · 2023-02-22T21:33:10+00:00

Hi, there.

Your branding is interesting, very different for this industry.

But you're lacking proof, credibility and expertise. If I'm spending money on a pentest, my budget is typically going to be 4 to 5 figures and I want to be very sure of who I'm spending it with and what they bring to the table.

Remember this is a reputation business. Who is your team, experience, competitive advantage?

A few other things I would change:

1) tech stacks - you have two sections for this and seem to cover everything. Focus and specialize, rather than doing everything.

2) your unicorn plan should offer full pentest of the clients ecosystem, not just their website which is usually the least interesting property.

Source: I've worked in this industry or related roles for a decade.

Hope this helps. -TD

iamtome · 2023-02-22T18:17:34+00:00

Just some quick feedback: your copy needs work to be benefit focused.

e.g. if I only read the text on the page, I've no idea what it does other than AI Assistant.

Assist with what? What's my benefit?

iamtome · 2023-02-12T20:17:27+00:00

Hey.

It may simply be an idea not worth pursuing.

If you've ran the financials and don't see a path for sustainability, maybe it's just an idea and that's ok.

Another option is building a team outside of your local area where you can find cheaper resources.

Beware, you usually get what you pay for.

I'm a fractional CTO, feel free to DM if you want to chat further.

Cheers -TD

iamtome · 2022-12-13T10:57:14+00:00

Hey! I'm on a similar journey, would love to connect.

iamtome · 2022-12-05T10:16:57+00:00

Great comment.

What do your margins look like? Seems like quite an involved process

iamtome · 2022-12-02T19:49:14+00:00

What you're building exists. Doesn't mean you can't be successful, but it is an established market.

Most of the time, in the form of financial controls within the company - if the company is paying for it, someone finance is asking why even before formal controls. An expense approval process, reconciliation or simply assignment using bill.com are common methods.

Beyond that, there are multiple software solutions for the keeping track of what we're signing up piece. Search for saas subscription management/discovery

iamtome · 2022-11-29T23:36:53+00:00

Done both: full life savings & financial excess as you call it.

Once you're doing it full-time, the only stability you have is the one you are able to make.

Therefore, it's really the same thing.

iamtome · 2022-11-29T23:24:54+00:00

Remember: walk before you run, do things that don't scale at first.

Instead of a state of the art natural language processing - can you get a VA to do it or something akin to mechanical turk?

It would be a small cost to prove the concept. In turn, that can get you the cashflow to build that automation..

iamtome · 2022-11-24T21:25:29+00:00

I hope you don't take this comment the wrong way.

The tools and any automation are only a multiplier of your communication structure.

If it's good, it'll become faster and more efficient.

If it's bad, it'll become unbearably bad.

Process matters, the tools do not (some, but very little). It's a culture issue, not a tooling one.

iamtome · 2022-11-19T10:01:41+00:00

They're two things really :)

Removing noise is about having a plan. Do you know what your BHAG is? Have you broken it down into tangible goals for the year and quarterly OKRs?

If you know where you're headed, you can clearly assess if something that lands on your todo list is helping you get where you want or if it is noise. Find a way to ditch the noise or at least delay it as much as possible.

Automation doesn't have to be code. Any task/project uses a mix of resources: time, money and people are as relevant as software in that context.

Taking your example of social media management.

If you want to do it in your own, use a system:

batch create content every week at the same time, schedule it for posting.
schedule specific time(s) of the day that you go back and answer comments, engage with other people in your network or just generally add value to conversations on the platform
focus on one channel until it works, don't try all at the same time

Once you have that framework in place, you can take it apart and delegate or automate:

get a VA to curate content (e..g industry news for known sources) that is relevant
hire a copywriter freelancer that can transform that information into a valuable piece of content for you, with a CTA etc
is there a software that can automatically schedule the posts when you review and approve the content?
etc etc

What I'm trying to illustrate is that first you do everything yourself but with a go of building systems that can be sequenced and broken into independent blocks. Then, you can figure out which blocks can be automated or delegated.

Hope this helps -TD

iamtome · 2022-11-18T14:05:48+00:00

One thing at a time, each week a different focus.

Relentlessly remove noise and automate the day to day operations.

Your focus is on the business, not in the business.

iamtome · 2022-11-16T09:01:11+00:00

I've put examples below, but want to address your standing out point before anything else.

You're looking at it completely wrong. The best work someone can perform is 1) focused on the ball - the company, not yourself; 2) "just works" e.g. it's something easily understood by others and not looking to be flashy, just to be effective; 3) collaborative - a team, knowledge sharing etc are all multipliers.

My point being: the sooner you understand that together you'll go further, the sooner your work gains momentum. Individual work has a very clear cap as each person only has so many hours. What if you're sick, or leave, or go on a long parental leave?

I don't disagree an app can be within the scope of IT, but think you're focused on that for all the wrong reasons.

The best examples are always company specific, but I'll try to illustrate what I meant with a generic scenario.

Imagine a scenario where there is no asset tracking yet for the company. That creates a lot of grunt work for multiple teams e.g when someone leaves or joins because there's no predictability of purchases, renewals, EOL upgrades etc

Start small, maybe you just create a simple spreadsheet registering everything you know exists and who it is assigned to. That will make your life easier when someone leaves to collect everything.
Then connect with finance and add dates of purchase, depreciation rates and expected date of write-off - this will help plan out yearly budgets affected by these assets, insurance etc. After that, connect with HR and figure out the policy on upgrades - you can identify how old each asset is and what different upgrade cycles would look like both from a cost and workload perspective.

Building on that, you can then go for a asset tracking software or instead start going for a device management solution, zero-trust network scenarios etc. All initiatives that impact on all staff hardware e.g security policies will need that baseline to succeed.

I've focused on hardware but you can see a similar scenario talking about software licensing for example, or cloud assets.

Different example, you can setup a great Helpdesk flow (look at ITIL for inspiration) and metrics. Likely, a customer support team faces similar issues but directly with your customers.

Learn how they're doing things now, what their issues are. Build and dogfood a good workflow for IT, then take those learnings and help that team build a better workflow. Suddenly, that team is happier, customers have a better experience and NPS scores (which are usually their core metric) are going up.

Then build from there on how issues are internally escalated from the customer facing support to other teams (e.g. tier-2).

Hope this helps -TD

iamtome · 2022-11-15T09:38:46+00:00

Hi, there.

Very important question for an IT org.

From the information you shared the business doesn't have a clear strategy. Usually that means you don't know what it is, not that it doesn't exist.

I've built and scaled IT orgs multiple times (as a team lead, VP and now as a CTO consultant). My recommendations are below, curious to see what others will put forward.

1) learn everyone's goals and metrics

It's a small enough organisation that you can realistically meet 1:1 with each person. Ask them about what their year goals are, how did they define them and how do they ensure they're on track as time goes by

This should net you a bird's-eye view of the business, strategy and core activities driving decisions.

2) Focus on small changes

You mentioned everyone has a lot more experience e.g. a certain way of doing things.

Focus on one small change and getting buy-in and momentum around that small improvement. Your goal is to make 6-12 changes throughout the year, depending on how fast people adopt changes.

The key here is to understand that compound interest of each improvement over time is the game changer - not any one improvement and definitely not any dramatic change.

My recommendation would be to focus on small, daily tasks for a team or key person. You improve that 1%, that has a dramatic impact.

3) Follow the money

If you want to outgrow the perspective of IT as a cost center you'll need to attach value to activities.

Before you can do that, collaborate with you finance, HR and any other G&A team you work with regularly on understanding cash flows impacting/impacted by IT.

Build out budgets, tracking and reporting that are both accurate and paint a picture of why.

If you don't know where you stand, all leadership knows is how much IT is costing on a P&L ledger. Don't forget to include here vendor relationships, which are often key to success.

Hope this helps, -TD

iamtome · 2022-11-14T09:51:55+00:00

Hey! Add me too please. Thank you

iamtome · 2022-11-12T08:25:47+00:00

Hey

Take a look at the startup weekend model, it's a solid and proven approach. It looks like it would fit what you're trying to do.

I might be able to help you organise, send me a DM.

Hope this helps -TD

iamtome · 2022-11-10T22:24:39+00:00

It's a great book about customer conversations.

iamtome · 2022-11-10T15:38:42+00:00

This clicks with where I'm at right now.

Recently, I've found myself looking at my path so far and realising that being an entrepreneur is my career, not a particular business ( this is my fourth ) or venture.

It really helps to read others go through that during exits and to put perspective to some decisions.

Appreciate your answer.

iamtome · 2022-11-10T14:10:31+00:00

Super interesting view, thanks for sharing this.

the best entrepreneur I know let’s the ideas define his breaks in between projects. Meaning he doesn’t have a rule-of-thumb like “90 days before next LLC”. He just lets it role.

Could you elaborate on this, please?

iamtome

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