Fractional CSO + AI Sales Systems

Your biggest deals
need a real game plan.

We map out the strategy for your high-stakes B2B accounts, then build tailored AI assistants that handle the research and grunt work. Show up to every deal fully prepared and get hours back every week.

Run an accelerator or founder program? We run workshops for your founders →

A sales leader in your corner

Someone who asks the right questions and learns how your business actually works before giving advice. No generic playbook, just a game plan built for you.

Tools built around your team

AI assistants tailored to how each member of your team actually sells, hosted by us or built inside the tools you already use.

Built and supported by us

We handle the build, hosting, and fixes.

Workshops

Learn how to sell. Optimize with AI.

A hands-on working session on the sales basics most founders never got taught: who to sell to, how to get in the door, and how to manage a deal from first call to close. Then we show you how to use AI to cut the busywork and spend more of your time being strategic.

For sales teams

Sharpen how your team finds and manages deals, then use AI to spend less time on admin and more time with buyers.

For accelerators and founder programs

A session for your founders on how to actually sell: finding the right buyers, getting the first meeting, running the deal, and using AI to move faster while they're still the ones selling.

01 / The problem

Stop running someone else's playbook.

Whether you're a founder who built a great product and got this far on your network, or you're running a team that's stuck, generic sales advice won't get you where you need to go. You need a game plan built around your buyers, your deals, and your people.

01

You built a great product. Selling it is a different job.

Plenty of founders land their first customers through their network, then hit a wall. We make it easy: who to go after, what to say, and what to do next with every deal.

02

Your team knows where things are falling apart. They won't say it in a meeting.

Very few people will say it bluntly to leadership. We get the truth from the field first, then build the game plan around what your team tells us, instead of forcing you into a framework.

03

Advice nobody has time to run is just a document.

Most consultants hand you a strategy deck and leave. A plan fails if running it takes hours of research and admin your team doesn't have. We build the tools that make it doable.

02 / Engagements

Five ways to work with us.

Audit

“We don't know where it's breaking.”

A confidential team survey, discovery calls, and industry research. We also find what each rep is already good at, so the game plan plays to real strengths instead of an ideal rep who doesn't exist. You get what we found and a game plan, then decide what to build.

AI readiness

“Our systems are a mess.”

AI can only work with what you give it. We go into your CRM and the systems around it and fix what needs fixing, with a strategy behind it, so everything supports how you actually sell.

Builds

“Our reps are buried in busywork.”

Custom assistants and automated workflows, tuned to how each rep actually works, hosted by us or built right inside the tools you already use. A strong closer who hates research gets the research handled.

Fractional CSO

“We need someone to run the offense.”

Ongoing sales strategy, coaching on your live deals, sales process design, and reporting guidance, sized to how much of us you need. For teams without a senior sales executive, or founders who are still the ones selling.

Workshops

“Our team needs to get up to speed.”

For your sales team, or for the founders in your accelerator or program. More on workshops →

Pricing. Every team and every build is different, so we don't publish prices. After an intro call, we'll follow up with pricing for your situation.

Strategy advice. We give strategy advice through a Fractional CSO retainer or a full project, never as a one-off. We want to know your business well before we tell you what to do.

Getting started. Nothing starts without a signed agreement.

What we don't do. We help you figure out which accounts to go after and how to work them. We don't run high-volume cold outreach or sell lead lists.

03 / How a build works

We do the heavy lifting.

Step 01

Ask

We learn from your team first, then hold short calls to understand where your process gets hung up.

Step 02

Decide

One strategy review, with a pre-read beforehand. We show you what we found and our recommended game plan. You decide what we tackle. That's where scope locks.

Step 03

Build

We build the tools against the systems you already use, then hand them over for a one-week trial with your reps. Two rounds of fixes are included.

Step 04

Run

Your team puts them to work. If we host them, we monitor them and keep them running. If they live in your own tools, we train your team to manage them. Fixes and changes are booked as support hours.

04 / Under the hood

What your IT team will ask.

For the IT and operations people who need to know how it runs.

Hosted by us, or built in your tools

We host your tools in a secure environment, build them right inside the platforms you already use, or connect them over MCP to the AI tools your team already has.

Secure connections

Connections to your email, calendar, and other tools use standard Google or Microsoft sign-in with scoped permissions. We never see or store your passwords, and you can revoke a connection at any time.

A hosted workspace, if you want one

Don't want your assistants inside your CRM or other AI tools? Use the Grayford Workspace instead: one place to run, test, and monitor everything we build for you.

Monitoring and support

We monitor everything we host and keep it running. If an integration breaks or you want a change, it's booked as support hours with us.

05 / Experience

Carried the quota first. Built the systems second.

On the field

Carried quota on strategic enterprise accounts, with deal cycles that ran one to two years and C-suite buying committees. Built a $1B pipeline and closed $712M.

Building the systems

Led the internal sales AI systems for a $14B global technology company: deciding what gets built, designing it, and rolling it out to an enterprise sales team, saving that team over 2,000 hours.

06 / Questions

Practical questions before booking a call

Why not just follow a proven sales framework?

Frameworks are a fine starting point, but they're built for someone else's buyers. We learn how your buyers buy and how your team works before we recommend anything, so the game plan actually fits you.

Why not just use AI ourselves?

You can, and we'll show you how in a workshop. But AI only speeds up what you're already doing. If the sales process underneath isn't working, AI just makes you faster at the wrong things. We get the strategy right first, then build AI around how your team actually works.

What if you can't help us?

We'll tell you. That's what the intro call and discovery are for: understanding your business and seeing whether we're the right fit. If we're not, we'll say so plainly.

Can we just get some quick strategy advice?

Not as a one-off. We give strategy advice through a Fractional CSO retainer or as part of a full project, because good advice depends on knowing your business well. A single call would only get you the same generic advice you can find anywhere.

Do you help us find new customers?

Yes, on the strategy side. We help you figure out who your best buyers are, how to reach them, and how to move a first conversation forward. What we don't do is run high-volume cold outreach for you or sell lead lists.

What if we don't have a formal sales process yet?

That's common. It's easier to build the right fundamentals from the start than to untangle a messy process two years down the road. We map the plays with you and equip your team from day one.

My team is small. Is an anonymous survey necessary?

Yes. Even with three reps, people rarely tell the boss the unvarnished truth about why deals get lost or where the tools get in the way. A confidential survey gets the real problems on the table.

Can you build inside the tools we already use?

Yes. We can build assistants and workflows right inside the platforms your team already works in, like your CRM, so there's nothing new to log into. If your data or systems need work first, that's what our AI readiness work is for.

Let's talk about your business.

A free 30-minute intro call, no sales pitch. We'll learn how your company sells today and where we might be able to help. If it makes sense, we'll set up a follow-up to walk through options and pricing. If we aren't the right fit, we'll tell you plainly.