GTM operations · Series A and B · Two builds at a time
I'm Will Chartain. As the first GTM operations hire at LegalOn, an AI contract review company, I built the revenue system from a blank HubSpot instance to multimillion ARR. Now I build that foundation for startups with reps on the floor and nobody owning ops, inside the CRM you already have, on a fixed fee.
Not a startup? AI setup and coaching for anyone →
The pattern
The version I see most at Series A is a handful of reps, no ops owner, and each rep uploading their own lists into the CRM. It gets more expensive with every hire: the next two reps double the untangling, and a new head of sales spends their first quarter auditing pipeline by hand.
The fix is unglamorous and fast. One governed account universe, an ownership model the system enforces, and stage definitions with entry and exit criteria, so the number you report to the board is a number you trust.
Sprints and pricing
Fixed scope, fixed fee and acceptance criteria written before we start. Software stays in your accounts and on your own bill.
$6,500
Credited in full toward a sprint if you sign within 30 days. The findings become its scope.
From $19,500
For reps colliding on accounts and a CRM nobody trusts.
Scoped after the Diagnostic
For when the pain is the forecast, usually ahead of a board meeting or a raise.
One or two days a week, three month minimum, then monthly. Forecast cadence, data quality, onboarding new reps into the model, monthly AI office hours for the team, and whatever the quarter demands. It's also the cleanest path to a permanent seat if you want one.
Stay on HubSpot or move to Salesforce? A requirements driven memo with decision criteria and the migration cost in rep hours. Platform neutral, so sometimes the answer is to cancel the migration.
AI in the revenue system
AI on top of a messy CRM just makes the mess faster. Once the account layer is sound, these two builds sit on top of it. I run the prospecting engine on my own pipeline today.
Account research, an ops and incumbent gate, and first touches drafted in each rep's own voice from a style guide built on their replied to messages. Runs on HubSpot and your enrichment tool. Reps approve every send, and every touch logs back to the record.
Four working sessions for up to fifteen reps, on Claude workflows wired to your cleaned CRM: account research, call prep, follow ups and prospecting. Ships with a shared prompt playbook and a usage policy your security team can approve.
Proof
How I work
Rep count and CRM, or take the scorecard. I'll tell you which sprint fits, or that you don't need one yet.
We agree on the problem in your numbers before anyone talks about scope.
I look before I touch. Nothing gets written until you've approved the fix list and the rollback has been tested.
Acceptance criteria are written in advance, everything lives in your accounts, and the runbook outlasts the engagement.
Questions buyers ask
You do. Every workflow, field, report and runbook lives in your CRM and your accounts, and tools are billed to you directly.
Your team running the system without me, checked against acceptance criteria we write down before the work starts.
I do, personally. There is no junior bench, and nobody else touches your systems without your written OK.
I build the foundation your first ops hire inherits. If you'd like me to be that hire, a fractional engagement is the cleanest way for both of us to find out.
I'm hands on in HubSpot, where I've done the admin and build work. I sold inside Salesforce for three years, and I stay neutral on platform decisions.
Bad data and unclear ownership. AI on a messy CRM sends the wrong message to the wrong person faster, which is why the account layer comes first.
The Diagnostic Sprint is $6,500 and is credited in full toward a sprint if you sign within 30 days. The Account Integrity Sprint starts at $19,500. Fractional work starts at $7,500 a month. Fees are fixed and agreed in writing before work starts.
About
I've worked in contract technology since 2014, selling to in house legal teams for over a decade. At Apttus I sold contract management to lawyers and procurement teams, working inside Salesforce every day. At LexCheck I started and hired the SDR team and ran business development, marketing and revenue operations. At Astera I ran a Dynamics to HubSpot migration and built the BDR function from zero.
Then LegalOn, where I was the first GTM operations hire and built the revenue system the company ran on. Rep, SDR manager, then ops builder. Having run every one of those motions in one system, I know which change to the account object quietly breaks the renewal report three months later.
I also use AI for most of my working day, and I run weekly sessions where friends bring what they're building and leave with it working. That practice is on its own page: AI setup and coaching.
Get in touch
Rep count, CRM and what's breaking. I'll reply within two business days and tell you honestly whether I can help.
Rather start with numbers? Take the scorecard. Or email billychartain@gmail.com.
