
Husband. Vertical AI CFO/COO @SITETechnolog. Former @OneTrust + @Celonis + @MorganStanley. All opinions my own. Not investment advice.
NYC
Joined August 2020
- Tweets3.2K
- Following1.6K
- Followers5.4K
- Likes3.5K
Thomas Robb ☁️ retweeted
AE to their SE after bringing on a customer who needs a ton of implementation support
Thomas Robb ☁️ retweeted
I read and love all your guys stuff so some very unsolicited advice on the off chance it’s helpful in return
If you REMOTELY have $600m of pipeline you should be hiring a sales team. A GTM engineer would be one small piece of that
A GTM engineer is exactly what it says… an engineer. They primarily make sure your pipeline and other sales/marketing activities flow to and get properly tracked in a CRM. This can be an extremely high leverage position especially if you get the right person (and attach them to the right team). They’re great at building scalable outbound infrastructure, AB testing messaging, tend to be pretty good with metrics. Very systems focus so not always great with 0-1 messaging or enterprise closing (just my experience). Your salary expectations are correct, but they don’t tend to get that much commission and 1% equity seems high.
My $0.02… either way take out “forward deployed” that makes it sound like they’re developing sales systems for your customers. They might partner closely with your FDE team once the deal is closed.
You then have a separate closer who takes raw pipeline and connects with the customer, creates/presents sales material, moves deals through the sales funnel and actually closes the deal. It looks like you guys are heavy vertical focused so getting a former IB is probably a smart play and worked well at Hebbia etc. Salary + Commission are about right. Industry rate is ~10% so $1m commission = $10m ACV which is probably a big enterprise deal or two for you guys. 1% equity also seems high here given the potential for high cash pay
So let’s say you do have $600m pipeline or someone is at least telling you that. Maybe it’s $300m once you clean it up and it hasn’t been qualified so close rate target is only 10% vs 20% industry. You’re looking at $3OM ACV. You’d then want someone in strategic finance/IB/consulting to help you understand your pipegen metrics, sales cycle lengths, and close rates. They’ll help you match your investments to the current opportunities and more importantly track/drive progress at each stage so the growth continues. It’s better to have the correct number and execute properly than to have for execution metrics on an inflated number. They will also help you communicate this all back to investors.
If this is at all helpful happy to jump on and explain more. Either way congrats on the pipeline (and please keep posting great harness posts)
HIGH PRIORITY HIRE @ VARICK: Forward Deployed GTM Engineer
We have ~$600M in pipeline and not enough people to close it. New leads come in every day from a mix of sources (X, our newsletter, email, DMs, etc.).
You'll be responsible for wrangling this pipeline: outbound, inbound, and even outbound on hiring (an extension of selling). You'll also have a huge impact on our messaging, marketing, design, and product roadmap, since you'll be on calls every week with dozens of the largest companies on earth, from the Fortune 500 up to the Fortune 10.
Applied AI is still early, and we're going to dominate it. You'll be central to driving the next 9 figures of revenue at Varick.
Comp: $150K-$200K base, up to 1% equity, and commission on every deal you work, up to $1M a year.
Have you done at least one of the following?
- Finished top 10% of your SDR, BDR, or AE team for 2+ quarters
- Spent 2+ years at a top bank, consulting firm, or PE fund with strong performance
- Started something of your own that made $100K+ in revenue
- Built your own outbound engine (Clay, scrapers, agents) and can show the reply rates
If you're a mercenary who's ready for long, intense hours, apply below or DM me.
$20k bonus if we hire someone you send my way.
I read and love all your guys stuff so some very unsolicited advice on the off chance it’s helpful in return
If you REMOTELY have $600m of pipeline you should be hiring a sales team. A GTM engineer would be one small piece of that
A GTM engineer is exactly what it says… an engineer. They primarily make sure your pipeline and other sales/marketing activities flow to and get properly tracked in a CRM. This can be an extremely high leverage position especially if you get the right person (and attach them to the right team). They’re great at building scalable outbound infrastructure, AB testing messaging, tend to be pretty good with metrics. Very systems focus so not always great with 0-1 messaging or enterprise closing (just my experience). Your salary expectations are correct, but they don’t tend to get that much commission and 1% equity seems high.
My $0.02… either way take out “forward deployed” that makes it sound like they’re developing sales systems for your customers. They might partner closely with your FDE team once the deal is closed.
You then have a separate closer who takes raw pipeline and connects with the customer, creates/presents sales material, moves deals through the sales funnel and actually closes the deal. It looks like you guys are heavy vertical focused so getting a former IB is probably a smart play and worked well at Hebbia etc. Salary + Commission are about right. Industry rate is ~10% so $1m commission = $10m ACV which is probably a big enterprise deal or two for you guys. 1% equity also seems high here given the potential for high cash pay
So let’s say you do have $600m pipeline or someone is at least telling you that. Maybe it’s $300m once you clean it up and it hasn’t been qualified so close rate target is only 10% vs 20% industry. You’re looking at $3OM ACV. You’d then want someone in strategic finance/IB/consulting to help you understand your pipegen metrics, sales cycle lengths, and close rates. They’ll help you match your investments to the current opportunities and more importantly track/drive progress at each stage so the growth continues. It’s better to have the correct number and execute properly than to have for execution metrics on an inflated number. They will also help you communicate this all back to investors.
If this is at all helpful happy to jump on and explain more. Either way congrats on the pipeline (and please keep posting great harness posts)
HIGH PRIORITY HIRE @ VARICK: Forward Deployed GTM Engineer
We have ~$600M in pipeline and not enough people to close it. New leads come in every day from a mix of sources (X, our newsletter, email, DMs, etc.).
You'll be responsible for wrangling this pipeline: outbound, inbound, and even outbound on hiring (an extension of selling). You'll also have a huge impact on our messaging, marketing, design, and product roadmap, since you'll be on calls every week with dozens of the largest companies on earth, from the Fortune 500 up to the Fortune 10.
Applied AI is still early, and we're going to dominate it. You'll be central to driving the next 9 figures of revenue at Varick.
Comp: $150K-$200K base, up to 1% equity, and commission on every deal you work, up to $1M a year.
Have you done at least one of the following?
- Finished top 10% of your SDR, BDR, or AE team for 2+ quarters
- Spent 2+ years at a top bank, consulting firm, or PE fund with strong performance
- Started something of your own that made $100K+ in revenue
- Built your own outbound engine (Clay, scrapers, agents) and can show the reply rates
If you're a mercenary who's ready for long, intense hours, apply below or DM me.
$20k bonus if we hire someone you send my way.
this is pretty cool @blader
For minimal direction, no real company data, and a relatively difficult/nuanced question it did a pretty good job capturing the big moving pieces and inputs of our business
A lot of the dynamics are how I build my LRP in excel and I could see the "excel" you built being the most important part of the product especially with a more experienced operator to build on it. Its a ai native anaplan with a bot so you don't need an implementation team
I could also see a founder just taking the exact output and not fully understanding/missing some of the important drivers of their business. Will be interesting to see how AI ramps to a replacing a finance team/CFO with no direction
Replying to @BreakingSaaS @blader
@BreakingSaaS Sorry about that. @Gerithecfo and I were arguing about the color scheme. We were also so distracted reading about all your cool work
Make sure you check out the Invoice Timing page.
Here it is! app.cfo.ai/s/5ec29e80-e93b-4…
Wow crazy impressive metrics
Five numbers tell you whether an AI business is a real business.
Gross retention.@WeAreLegora is 95%. Customers who bought last year are still here this year. If this one is broken, nothing downstream matters.
NRR. Ours is 300%+. Gross retention is the floor. NRR is how much taller customers build on top of it. We don't sell shelf-ware.
DAU/MAU. Ours is north of 50%, and the average active user spends 17 hours a month in the product. A rollout tells you a firm has signed. This indicates the work actually matters, and it moves here before it appears in retention or NRR.
Win-rates. Our August pilot closed-won-win rate was 78%. Winning roughly 4 out of 5 competitive pilots is downstream from offering a superior product.
Gross margin. The one that matters most. Ours is positive and improving every quarter. Our customers want Legora to be a long-term partner, and this is what makes that possible.
There's a shorter route: Price below what it costs to serve, book the logo, and hop on a never-ending fundraise treadmill to pay for it. The top line goes up, everyone claps, and every new customer costs more than they pay.
Scaling a negative margin only exaggerates the problem. The whole point of scale is that the margin improves as you go up. Ours does. That's the only version of this business worth building.
Opus 5 shipped. Now ship me remote control for Claude in Excel and I'm closing the books from a beach chair.
Anyone have good data on what these AI services companies are raising at?
Assuming it’s some sort of discount to high growth SaaS but economics and TAM are massive
@jaminball maybe?
Thomas Robb ☁️ retweeted
Subsidies of AI services are part of customer acquisition cost (CAC). It's an up front cash expense. 25iq.com/2016/12/09/why-is-c…
Thomas Robb ☁️ retweeted
Hot take
This CAN be a useful metric
BUT
- most teams aren’t smart enough to know how to use it
- drink their own koolaid and calculate other metrics short hand off it (cash/collections)
- don’t have the political capital to use the real metrics when/where it matters
Usually all 3
Good luck out there
It’s time to expose a huge scam in AI startups: Contracted ARR
The reason many AI startups are crushing revenue records is because they are using a dishonest metric
The biggest funds in the world are supporting this and misleading journalists for PR coverage.
The setup: Company signs 3-year enterprise deals. Year 1 is discounted (say $1M), Year 2 steps up ($2M), Year 3 is full price ($3M).
They report $3M as “ARR” — even though they’re only collecting $1M right now.
The worst part: The customer has an opt-out option at 12 months! It’s not actually a 3 year contract.
In the chart below, by Q5 the company is trumpeting ~$100M “ARR” to press, while actual cash-generating, in-effect ARR is ~$35M. That’s ~3x inflation.
On top of this, enterprise AI companies are bundling full-time “forward deployed engineers” into deals massively reducing margins, sometimes producing Year 1 negative margins.
At some point customers are going to start triggering their opt-out clauses or aggressively negotiating down Year 3 pricing.
And a wave of enterprise AI companies may collapse.
Hot take
This CAN be a useful metric
BUT
- most teams aren’t smart enough to know how to use it
- drink their own koolaid and calculate other metrics short hand off it (cash/collections)
- don’t have the political capital to use the real metrics when/where it matters
Usually all 3
Good luck out there
It’s time to expose a huge scam in AI startups: Contracted ARR
The reason many AI startups are crushing revenue records is because they are using a dishonest metric
The biggest funds in the world are supporting this and misleading journalists for PR coverage.
The setup: Company signs 3-year enterprise deals. Year 1 is discounted (say $1M), Year 2 steps up ($2M), Year 3 is full price ($3M).
They report $3M as “ARR” — even though they’re only collecting $1M right now.
The worst part: The customer has an opt-out option at 12 months! It’s not actually a 3 year contract.
In the chart below, by Q5 the company is trumpeting ~$100M “ARR” to press, while actual cash-generating, in-effect ARR is ~$35M. That’s ~3x inflation.
On top of this, enterprise AI companies are bundling full-time “forward deployed engineers” into deals massively reducing margins, sometimes producing Year 1 negative margins.
At some point customers are going to start triggering their opt-out clauses or aggressively negotiating down Year 3 pricing.
And a wave of enterprise AI companies may collapse.
Thomas Robb ☁️ retweeted
Worth reading. Here’s the part I thought was most interesting:
“Do everything you can to instill this entrepreneurial DNA within your company. Hire and promote people who truly get it. And part with those who don’t. Compensation structures probably have to change. Talent assessment very likely has to change.”
I think this is the most interesting part because almost no incumbent software company is operating with the urgency they need to change their culture.
And culture is at core of everything. Without fixing the culture they can’t survive
The hour is getting late. And I fear most do not realize it. Or perhaps worse, they realize it but are unable to do anything to fix their broken cultures.
At a time like this, maybe you need a Satya-type figure to truly re-found the company. But Satya was once in a generation. For most of these companies, nobody is coming to save them
Are GitHub’s the new Substack?
Wow, this tweet went very viral!
I wanted share a possibly slightly improved version of the tweet in an "idea file". The idea of the idea file is that in this era of LLM agents, there is less of a point/need of sharing the specific code/app, you just share the idea, then the other person's agent customizes & builds it for your specific needs.
So here's the idea in a gist format: gist.github.com/karpathy/442…
You can give this to your agent and it can build you your own LLM wiki and guide you on how to use it etc. It's intentionally kept a little bit abstract/vague because there are so many directions to take this in. And ofc, people can adjust the idea or contribute their own in the Discussion which is cool.
Thomas Robb ☁️ retweeted
This is exactly how I manage my set up
Granola > Obsidian > Claude Code
Input raw data
Have AI automate a wiki across:
- Time
- People
- Projects
breakingsaas.com/p/ai-cfo-br…
LLM Knowledge Bases
Something I'm finding very useful recently: using LLMs to build personal knowledge bases for various topics of research interest. In this way, a large fraction of my recent token throughput is going less into manipulating code, and more into manipulating knowledge (stored as markdown and images). The latest LLMs are quite good at it. So:
Data ingest:
I index source documents (articles, papers, repos, datasets, images, etc.) into a raw/ directory, then I use an LLM to incrementally "compile" a wiki, which is just a collection of .md files in a directory structure. The wiki includes summaries of all the data in raw/, backlinks, and then it categorizes data into concepts, writes articles for them, and links them all. To convert web articles into .md files I like to use the Obsidian Web Clipper extension, and then I also use a hotkey to download all the related images to local so that my LLM can easily reference them.
IDE:
I use Obsidian as the IDE "frontend" where I can view the raw data, the the compiled wiki, and the derived visualizations. Important to note that the LLM writes and maintains all of the data of the wiki, I rarely touch it directly. I've played with a few Obsidian plugins to render and view data in other ways (e.g. Marp for slides).
Q&A:
Where things get interesting is that once your wiki is big enough (e.g. mine on some recent research is ~100 articles and ~400K words), you can ask your LLM agent all kinds of complex questions against the wiki, and it will go off, research the answers, etc. I thought I had to reach for fancy RAG, but the LLM has been pretty good about auto-maintaining index files and brief summaries of all the documents and it reads all the important related data fairly easily at this ~small scale.
Output:
Instead of getting answers in text/terminal, I like to have it render markdown files for me, or slide shows (Marp format), or matplotlib images, all of which I then view again in Obsidian. You can imagine many other visual output formats depending on the query. Often, I end up "filing" the outputs back into the wiki to enhance it for further queries. So my own explorations and queries always "add up" in the knowledge base.
Linting:
I've run some LLM "health checks" over the wiki to e.g. find inconsistent data, impute missing data (with web searchers), find interesting connections for new article candidates, etc., to incrementally clean up the wiki and enhance its overall data integrity. The LLMs are quite good at suggesting further questions to ask and look into.
Extra tools:
I find myself developing additional tools to process the data, e.g. I vibe coded a small and naive search engine over the wiki, which I both use directly (in a web ui), but more often I want to hand it off to an LLM via CLI as a tool for larger queries.
Further explorations:
As the repo grows, the natural desire is to also think about synthetic data generation + finetuning to have your LLM "know" the data in its weights instead of just context windows.
TLDR: raw data from a given number of sources is collected, then compiled by an LLM into a .md wiki, then operated on by various CLIs by the LLM to do Q&A and to incrementally enhance the wiki, and all of it viewable in Obsidian. You rarely ever write or edit the wiki manually, it's the domain of the LLM. I think there is room here for an incredible new product instead of a hacky collection of scripts.
This is exactly how I manage my set up
Granola > Obsidian > Claude Code
Input raw data
Have AI automate a wiki across:
- Time
- People
- Projects
breakingsaas.com/p/ai-cfo-br…
LLM Knowledge Bases
Something I'm finding very useful recently: using LLMs to build personal knowledge bases for various topics of research interest. In this way, a large fraction of my recent token throughput is going less into manipulating code, and more into manipulating knowledge (stored as markdown and images). The latest LLMs are quite good at it. So:
Data ingest:
I index source documents (articles, papers, repos, datasets, images, etc.) into a raw/ directory, then I use an LLM to incrementally "compile" a wiki, which is just a collection of .md files in a directory structure. The wiki includes summaries of all the data in raw/, backlinks, and then it categorizes data into concepts, writes articles for them, and links them all. To convert web articles into .md files I like to use the Obsidian Web Clipper extension, and then I also use a hotkey to download all the related images to local so that my LLM can easily reference them.
IDE:
I use Obsidian as the IDE "frontend" where I can view the raw data, the the compiled wiki, and the derived visualizations. Important to note that the LLM writes and maintains all of the data of the wiki, I rarely touch it directly. I've played with a few Obsidian plugins to render and view data in other ways (e.g. Marp for slides).
Q&A:
Where things get interesting is that once your wiki is big enough (e.g. mine on some recent research is ~100 articles and ~400K words), you can ask your LLM agent all kinds of complex questions against the wiki, and it will go off, research the answers, etc. I thought I had to reach for fancy RAG, but the LLM has been pretty good about auto-maintaining index files and brief summaries of all the documents and it reads all the important related data fairly easily at this ~small scale.
Output:
Instead of getting answers in text/terminal, I like to have it render markdown files for me, or slide shows (Marp format), or matplotlib images, all of which I then view again in Obsidian. You can imagine many other visual output formats depending on the query. Often, I end up "filing" the outputs back into the wiki to enhance it for further queries. So my own explorations and queries always "add up" in the knowledge base.
Linting:
I've run some LLM "health checks" over the wiki to e.g. find inconsistent data, impute missing data (with web searchers), find interesting connections for new article candidates, etc., to incrementally clean up the wiki and enhance its overall data integrity. The LLMs are quite good at suggesting further questions to ask and look into.
Extra tools:
I find myself developing additional tools to process the data, e.g. I vibe coded a small and naive search engine over the wiki, which I both use directly (in a web ui), but more often I want to hand it off to an LLM via CLI as a tool for larger queries.
Further explorations:
As the repo grows, the natural desire is to also think about synthetic data generation + finetuning to have your LLM "know" the data in its weights instead of just context windows.
TLDR: raw data from a given number of sources is collected, then compiled by an LLM into a .md wiki, then operated on by various CLIs by the LLM to do Q&A and to incrementally enhance the wiki, and all of it viewable in Obsidian. You rarely ever write or edit the wiki manually, it's the domain of the LLM. I think there is room here for an incredible new product instead of a hacky collection of scripts.
Thomas Robb ☁️ retweeted
Like every CFO not looking to get replaced in the next 12 months, I’ve been diving DEEP into AI.
breakingsaas.com/p/ai-cfo-br…
Like every CFO not looking to get replaced in the next 12 months, I’ve been diving DEEP into AI.
breakingsaas.com/p/ai-cfo-br…
Thomas Robb ☁️ retweeted
Really enjoyed the deck @loganbartlett and team just shared on the state of Software, wanted to pull out a few things that caught my eye:
1. AI-native companies are growing faster AND more efficiently
The growth rates are really staggering. And they’re doing it with very few people. The demand for AI is insatiable, like nothing we have ever seen, and is diverting budget away from traditional software. This is an existential moment for the incumbents. I’ve been saying Accelerate or Die for months. The accelerating is unprecedented, and the growth is coming at the expense of SaaS 2.0. Only death can pay for life
2. They’re doing it without going head-to-head with incumbents
This is probably the most interesting slide to me. These AI-native businesses are growing so fast by using two approaches:
A) Finding a wedge into the enterprise, scaling quickly, then trying to expand
B) Building AI-native Systems of Record from below. @arampell calls this “Greenfield Bingo.” New businesses/SMB have zero/low switching costs, so AI-native CRM/HR/ERP companies can take share and march upmarket from below
Both of these are particularly tricky for incumbents to defend against. They simply aren’t able to move quickly enough to build compelling AI point solutions, and they’re struggling to defend downmarket while also defending the enterprise (bimodal go-to-market and running multiple service models in one company is incredibly difficult)
3. Incumbents scale by throwing people at the problem
This has been the dirty little secret of SaaS for 15 years. It’s basically impossible to grow revenue faster than headcount. Some companies like Shopify did it by layering on payments. Consumption-based companies have been doing it. The AI native companies have this figured out. The incumbent, seat-based, companies simply have never been able to decouple revenue from headcount. They will have to learn or die
4. Incumbents have the right to win but they are failing to capture the moment
As I’ve said before, the CIO wants to stick with their current vendors. They WANT to buy AI solutions from the incumbents. The problem is their solutions suck. @jasonlk has been all over this. These incumbents have a shrinking window of time where they have the advantage, but that window is shrinking. Rapidly.
When are we getting this for @GeminiApp ?
Replying to @claudeai
Claude in PowerPoint is now available in research preview for Max, Team, and Enterprise.
Claude reads your layouts, fonts, and slide masters to stay on-brand — whether you're building from a template or generating a full deck from a description.

























