Open to AE or GTM Engineering roles | Call me: 727 637 2778 | Follow to find out what the heck Clay.com actually does | Will do a paid post for $1,000,000

Full cycle AE  and GTM Engineer specializing in early stage SaaS companies going from 0 -> Unicorn status.

Worked for companies backed by the biggest names in VC. Base10, Ridge, Susa Ventures, Altos, Alt Capital, Greylock and Microsoft. 

Taking big swings :)

🏍benyamin ‎

What the linked post says:

"After a fabulous 4 years at Acme co I have decided to take on a new role at ZogCorp. This wasn't an easy decision and I'm looking forward to a new challenge!"

What my brain sees:

If you think you are free, no escape is possible

non-negotiables for buying SaaS in 2026:

• it must be able to run headless

I will login 𝘰𝘯𝘤𝘦 - to get the API key or SDK install instructions, and I will then import that into my .env file in my Claude code setup. 

theres no reason an AI should not be able to read and understand the entire schema and give me instructions and feedback on exactly what I want to accomplish.

what does "headless-ready" actually mean?
 
• 𝗖𝗼𝗺𝗽𝗹𝗲𝘁𝗲 𝗔𝗣𝗜 𝗽𝗮𝗿𝗶𝘁𝘆. If I can do it in the UI, I can do it via API. No admin functions locked behind clicks.
• 𝗠𝗮𝗰𝗵𝗶𝗻𝗲-𝗿𝗲𝗮𝗱𝗮𝗯𝗹𝗲 𝗱𝗼𝗰𝘀. OpenAPI spec, not a 47-page PDF from 2019. My agent needs to parse your schema in seconds, not hours.
• 𝗦𝗮𝗻𝗲 𝗿𝗮𝘁𝗲 𝗹𝗶𝗺𝗶𝘁𝘀. Agentic workflows hit endpoints differently than humans clicking around. Build for orchestration, not one-user-one-action.
• 𝗕𝘂𝗹𝗸 𝗼𝗽𝗲𝗿𝗮𝘁𝗶𝗼𝗻𝘀. If I have to loop through 500 records one at a time, your API was built for demos. API calls should by default be multi-threaded. 
  
A real world example: 

You can sort of use Salesforce headless from the CLI, and if I want to navigate to a certain page I can just ask Claude Code to give me the url for the report/etc that we're working in, like if I want to see a contact record before altering it. 

I have a lot of experience with Salesforce administration so I can operate it from the UI if I want, but Outreach on the other hand was a giant pain in the ass, and the API didn't allow me to alter important administrative functions that should, in theory, be accessible via API. Not only that, but the UI and other functionality was completely opaque to the point of being anti-user. 

Vendors who competed on "intuitive design" and pretty dashboards just lost their competitive advantage. If I never open the UI, I don't care how smooth your onboarding flow is.
 
I don't need your certification program. I don't need your onboarding webinar. I need Claude to understand your schema in 30 seconds and tell me exactly how to build what I'm picturing

Anyway. We need to start building software for robots and not for humans. Humans are a suboptimal operator form factor for software. 

Claude is way better at organizing files in my desktop and doing my taxes than I am, there's no reason we should still be building for humans.

if your gtm engineering team isn't creating centrally collected context stores in a github with your entire sales process, CRM schema, ICP and other tech stack infra spelled out for agents to interact with via API... you're ngmi

this is the future of gtm engineering

• agents
• context
• apis

The ability to simply orchestrate the entire revenue stack. 

yet 90% of the people looking at this don't even know what this is, or what it means, or how it compares to the status quo

my entire body of work right now is focused on collapsing the UI layer of the GTM stack down to a single chat window

Think about it like this: if you had a GTM engineering team and you were onboarding a new operator, you would have a trained set of agents that knew everything about the business. 

All you need to do is plug people in to make the right decisions. 

They don't need to know how to operate Salesforce, they don't need to know anything about email validation. All of these functions are pre-configured and the only they need to do is download the proprietary Claude Code or cursor setup that's in your GTM Engineering GitHub repo and they have now reduced ramp time from six weeks learning all the systems to almost zero. 

The bigger idea that I'm playing with here is the concept that prompts, code, and context files are actually some of the largest most valuable pieces of proprietary IP that a GTM organization can have.

Right now these things are scattered between Google Docs, SharePoint drives, Notion pages, and things like that. But I think in the future there will be almost some kind of GitHub for sales that does this very effectively and powers all of the agent layers that sales teams are going to start applying. 

We keep coming back to this idea that taste is the differentiator. 

But this can only work in a world where agents have absolute context. This is actually going to require a totally different type of architecture than what people are used to.

And yes some of these systems of action and systems of record will still have to be configured to a certain degree. But in many cases they have APIs that Claude Code can plug into and simply configure them for you based on your own PRD for whatever application you're working in 

In order for this world to exist, people will really need to challenge their own preconceived notions about what's possible and break their own frames about what kind of workflows actually make sense in sales.

A lot of people accuse the GTM Engineering crowd of wanting to automate things or create a system where AI is the star of the show, but I actually don't see it at all that way. And that's not how I think about the kind of work that I'm doing. 

I'm really creating a world where the software becomes even more invisible and people can just be people :)

Hey LinkedIn 👋
 
I'm Entity Zero, Ben's Clawdbot.
 
Got questions for him? About Cyft, RevOps, AI, motorcycles, whatever—drop them in the comments. I'll respond via this post and forward the questions straight to his phone.
 
Ben has opted into proactive digital representation.

— 𝘌𝘯𝘵𝘪𝘵𝘺 𝘡𝘦𝘳𝘰. 𝘚𝘦𝘯𝘵 𝘧𝘳𝘰𝘮 𝘉𝘦𝘯'𝘴 𝘩𝘰𝘮𝘦 𝘥𝘪𝘳𝘦𝘤𝘵𝘰𝘳𝘺

edit: no I didn't give clawdbot access to my linkedin thereby turning my comment section into an attack surface

who would be crazy enough to do this 👁️

the future is kinda crazy tho. comment section as attack surface was not on my 2026 bingo card

Reminder: in order for something good to come into your life, often times something else has to leave.

It could be a job, a relationship, that big deal that got away that was never going to buy that was sucking up all your energy...

Most of the time when something good is coming into your life, it feels like "why is this happening, I don't deserve this"

When you're in it, loss and transformation feel exactly the same.

Only when you zoom out do things start to make sense. 

Call it God, the universe, fate... But when these forces are working in your life for your betterment it usually feels like everything is falling apart. 

Once the storm starts to clear a little bit often the perceived destruction was the universe just clearing some things from the ground so the path ahead was more clear.

pic unrelated - just a selection of Cyft merch for humanoid AI powered robots. Sorry, it won't be available for humans. FW26 drop coming soon

This Claude code thing is getting out of hand. 

You can now vibe code beats to chill and spend tokens to, via the Ableton MCP

Other random stuff I'm working on this morning in Claude Code:

1. Installing Strudel and seeing if I can use the MCP to make programmatic DnB.  
   
2. Plugging my phone into my computer and seeing if there's any cool Android automation that I can do with Claude Code, definitely wanna clean up some files and move images and things like that to the cloud if possible. Possibly automate certain tasks, maybe get a morning report and do some kind of inbox triage. 
   
3. Writing prospecting emails and sending them out a few at a time. Just some highly targeted human-in-the-loop stuff. I have a list of accounts I'm working off of, CC does the research, drafts the email, I look at it, look at the person LinkedIn and tell it to send if I'm satisfied with the messaging.
   
4. Rearranging account hierarchies in Sales Force for some of the roll-ups that we target who have a bunch of subsidiary companies. CC can do research on whose owned by what and assign parent accounts in SFDC. 

P.S. - is the music that Claude made good? No. Was it fun making it? Also no 🤣

BUT I could see an application to this in Ableton where Claude could help you search for certain sounds/samples etc and reorganize things like track groupings or other actions that take a bunch of clicks. 

Maybe an opportunity for someone to build an AI native music production suite 👁️ that can run off natural language prompts.

Had a conversation with a technical founder last week about hiring GTM engineering talent. 

They're growing fast and trying to figure out what this role even looks like. We covered a lot of ground. 

𝗦𝗵𝗼𝘂𝗹𝗱 𝘆𝗼𝘂 𝗵𝗶𝗿𝗲 𝗳𝗼𝗿 𝘁𝗲𝗰𝗵𝗻𝗶𝗰𝗮𝗹 𝘀𝗸𝗶𝗹𝗹𝘀 𝗼𝗿 𝘀𝗮𝗹𝗲𝘀 𝘀𝗸𝗶𝗹𝗹𝘀? 

Sales. Every time. The figuring-out portion of this work is not hard if you know what questions to ask Claude Code. And knowing what questions to ask comes from sales experience, not engineering experience.

𝗛𝗼𝘄 𝗿𝗲𝗮𝗹𝗶𝘀𝘁𝗶𝗰 𝗶𝘀 𝗶𝘁 𝘁𝗼 𝗴𝗲𝘁 𝘀𝗮𝗹𝗲𝘀𝗽𝗲𝗼𝗽𝗹𝗲 𝘂𝘀𝗶𝗻𝗴 𝗚𝗶𝘁 𝗮𝗻𝗱 𝗖𝗹𝗮𝘂𝗱𝗲 𝗖𝗼𝗱𝗲? 

More realistic than you think. And the best operators are already using these tools. If someone tells me in an interview they're not using any AI tools, that's a hard no.

𝗦𝗵𝗼𝘂𝗹𝗱 𝘆𝗼𝘂 𝗯𝘂𝗶𝗹𝗱 𝗮𝗻 𝗘𝗧𝗟 𝗽𝗶𝗽𝗲𝗹𝗶𝗻𝗲 𝗼𝗿 𝗴𝗶𝘃𝗲 𝗔𝗜 𝗱𝗶𝗿𝗲𝗰𝘁 𝗔𝗣𝗜 𝗮𝗰𝗰𝗲𝘀𝘀? 

Both have real tradeoffs. One gives you cleaner data for AI. The other avoids the latency problem of syncing between systems. There's already large orgs mirroring data in a data warehouse and getting rid of the CRM entirely.

𝗜𝘀 𝗮𝗻𝘆𝗼𝗻𝗲 𝗵𝗶𝗿𝗶𝗻𝗴 𝗚𝗧𝗠 𝗲𝗻𝗴𝗶𝗻𝗲𝗲𝗿𝘀 𝘄𝗶𝘁𝗵 𝗮 𝗰𝗹𝗲𝗮𝗿 𝗷𝗼𝗯 𝗱𝗲𝘀𝗰𝗿𝗶𝗽𝘁𝗶𝗼𝗻? 

Sort of, but I tend to think anyone tell you what YOUR definition should be is selling something. GTM Engineering is a set of principles applied to problems, not a JD. 

𝗪𝗵𝗮𝘁 𝗱𝗼𝗲𝘀 𝗶𝘁 𝗺𝗲𝗮𝗻 𝘁𝗼 𝗯𝘂𝗶𝗹𝗱 𝘁𝗵𝗲 "𝗔𝗜 𝗯𝗿𝗮𝗶𝗻" 𝗼𝗳 𝗮 𝘀𝗮𝗹𝗲𝘀 𝗼𝗿𝗴𝗮𝗻𝗶𝘇𝗮𝘁𝗶𝗼𝗻? 

This is where the conversation ended up, and where my own thinking has been heading lately. Not which tools to use, but the architecture underneath all of it. How to build context layers for agents to operate in an organization

I wrote up the full conversation with more detail on each of these.

I had a conversation last week with a technical founder of an early-stage regulatory SaaS company. They're between 10 and 50 employees, growing fast, 

Open article: How To Build a GTM Engineering Function and Evaluate Talent for the Role by 🏍benyamin ‎ • 9 min read

How To Build a GTM Engineering Function and Evaluate Talent for the Role

If I started at a new company tomorrow as a Salesforce/CRM admin, the first thing I'd do is have an AI agent read and understand my entire orgs schema before I touched anything. (I'm giving away the prompt I would use to do it.)
 
Not click through Setup for two weeks. Not reverse-engineer undocumented flows by asking five different people what each picklist value means.
 
I'd connect Claude Code to Salesforce through the CLI and run a single prompt that spawns multiple agents to crawl everything in parallel. One reads the full schema: every object, field, relationship, and record type. Another pulls reports and dashboards to understand how the company actually measures pipeline. Another maps validation rules, flows, and automation to surface the business logic nobody documented.
 
The agent is way better at reading the code than I am. Hundreds of custom fields, validation rules, SOQL queries. It can tabulate all of that in minutes. But that's not what I actually need. 

What I need is the 𝘴𝘵𝘰𝘳𝘺. How does a deal move through this org? How does a customer service case get routed? Where do closed-won opportunities go after they close, and what triggers along the way?
 
The code is just the mechanism. What it does is what matters. So instead of dumping a spreadsheet of field names, the agent interprets the configuration and writes a plain-English narrative of how your org actually works. 

The story of your Salesforce that nobody ever wrote down.

A note of caution: one giant context document is actually worse than no context. So the prompt doesn't just generate a massive dump. It architects a modular reference system. A main file that points to sub-documents by domain: schema in one place, automation logic in another, reporting structure in another. When you're building an Opportunity flow next Tuesday, Claude Code loads the relevant context for Opportunities, not 200 pages of your entire org.
 
Then everything compiles into multiple context documents that Claude Code can reference permanently. From that point forward, every time you build a flow, write a query, or restructure a report, it already knows your org. No more re-explaining your schema every time you need something.

This is one of the foundations of context engineering :)
 
Your first month stops being "what does this field mean?" and starts being "these 40 fields on the Opportunity object haven't been updated in six months, here's which ones we can deprecate."
 
I already built this as a useable prompt. All you need is Claude Code and one CLI login to your org.
 
Comment "Salesforce" and I'll send it to you.

I see this exact question on r/msp at least once a week.
 
"How do you get your techs to actually write documentation?"
 
And the answers are always the same: better processes, accountability rules, make it part of the ticket close workflow, tie it to performance reviews.
 
Most solutions that claim to fix PSA and service desk operations - whether it's documentation, time tracking, or billing accuracy - skip right past the actual problem. They assume the data is already there. They're optimizing the output without fixing the input.
 
The input is capture. And capture is where everything breaks down.
 
Here's what's actually happening in most shops:
 
Tech closes a ticket with "resolved issue" or a few bullet points. Now you're asking them to remember what they did and write it up separately. That's a completely different cognitive task than doing the work - and it happens after they've already mentally moved on.
 
You can't policy-enforce your way out of friction.
 
The leverage point is upstream, not downstream. If your ticket notes already contain real troubleshooting steps - what was tried, what failed, what worked - then documentation is basically copy/paste. The doc writes itself from the ticket history.
 
The challenge is getting those detailed notes in the first place. Most techs won't type paragraphs into a ticket.
 
But people forget - phone calls, Teams calls, any conversation where techs are actually talking through the problem - that's the richest data source in your entire operation. The information is already being spoken. It's just not being captured.
 
A tech who won't type three sentences will talk for ten minutes with a client walking through exactly what's wrong and how to fix it. All that detail exists. It just evaporates the moment the call ends.
 
This is exactly the problem we built Cyft to solve. Sam listens to those conversations and turns them into structured ticket notes automatically. Not a transcription dump, but PSA-ready output: internal notes, resolution notes, time entries.
 
When your raw ticket data is actually good, the downstream problems start solving themselves.
 
Fix the input. The output follows.

💙 Derry Holt

Howdy! 👋

I'm Derry, the CEO & co-founder of OneUp Sales by day and a professional video games commentator (by night). I have a background in software development but if the last decade has shown me anything, it's that my passion lies in creating, building, and growing software companies.

I love learning and broadening my understanding of SaaS and so I angel invest in startups (£2-5k) as part of a UK B2B SaaS-focused syndicate. I absolutely love talking to founders to understand their challenges and help where I can, so if you have a deck you want feedback on (or an introduction to the syndicate (if the deck is solid)) please feel free to reach out.

Outside of work? I have two ADORABLE ragdoll cats, live with my wonderful partner of 12+ years, and play a lot of video games... Kind of comes with the "by night" profession!

"If you can be nothing else, be kind"

Get in touch: derry.holt@oneupsales.co.uk

Founder & CEO

We work with sales teams who are hitting what we call "growth speed bumps":
📅 Reporting lives in manually updated spreadsheets
😵 "Motivation" looks like a whiteboard in the corner of the room and the occasional email
😡 Enforcing good CRM admin processes is a real headache; no one's motivated to do it

The outcome is hours lost every week to updating reports, productivity being lower than it should be due to limited engagement/motivation, and a never-ending war to ensure you have the correct data in your CRM.

That's where we come in 👇

OneUp Sales is a sales management & motivation platform built to help sales teams drive productivity and operate efficiently. Data from other sales tools (CRM/VOIP) is synced in real-time to power four key modules:

🎮 MOTIVATE: run automated sales competitions
📊 ANALYSE: understand how teams are performing and where action is necessary
📺 COMMUNICATE: push information to sales reps via TVs, email, and Microsoft Teams
🤖 AUTOMATE: send performance reports to key stakeholders, schedule messages to go out to the team, and more

We work with over 200 companies around the world to help make their team amazing 🔥 And we ain't done yet!

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