I've spent 15+ years inside growth-stage companies watching this pattern repeat. That experience led to two bodies of work—one for professionals building independent practices, one for revenue operators navigating what comes next.

The Fractional Institute — for professionals building expertise-based practices

Going fractional sounds simple: you have expertise, companies need it, you connect the two. But most people who make this leap aren't failing because they lack skill. They're trapped by outdated expectations and roles that no longer fit how companies buy.

Three books address different parts of the journey:
→ The Fractional Operator — the reality of executive-level work without a safety net
→ The Fractional Practice — the complete operational playbook (positioning through exits)
→ The Fractional Trap — why revenue specialists are losing ground, and what replaces them

The Fractional Practice Course turns those frameworks into a 90-day launch plan with templates, scripts, and artifacts.

More at TheFractionalInstitute.com

Chief Revenue Architect — for revenue operators evolving past execution

The Fractional Trap names a problem. Chief Revenue Architect is the solution, specifically for fractional CMOs, CROs, and RevOps leaders feeling the hard edges of their roles fade as AI absorbs execution.

Most companies don't have a marketing problem. They have a systems problem. The Rise of the Chief Revenue Architect defines the role emerging as execution automates and system design becomes the real leverage.

The CRA Course (coming soon) is for operators ready to move into work AI can't replace: designing systems, governing decisions, creating leverage across revenue.

AA+OS is the operating system I built for founder-led companies that need their revenue engine to run without constant oversight.

More at ChiefRevenueArchitect.com

The throughline:

If you're considering going fractional, start with the practice.
If you're already fractional in revenue and feeling the ground shift, the architecture work is where this is heading.

Different starting points. Same destination: building leverage that compounds.

Will G.

One "yes" cost me 70 days and every dollar of profit on that client.

I was out for the night when my phone buzzed. New client. CEO. Panicking.

"We have a problem. I need your help. Tonight."

It was late. I did not have my head in the game. But he was panicked, and I wanted to be the guy who shows up.

I accepted. That one yes turned into 70 days of hell.

The "problem" wasn't a quick fix. It was systemic. A mess that touched everything. Way outside our original scope.

But I'd already said yes. So I kept going. I burned double the hours I'd scoped.  My profitability on that engagement went negative. All because I said yes to calm a panicky CEO on a Tuesday night.

Here's how I handle it now:

𝗜𝗻 𝘁𝗵𝗲 𝗺𝗼𝗺𝗲𝗻𝘁, 𝗯𝘂𝘆 𝘁𝗶𝗺𝗲. "Let me look at this tomorrow and tell you what it would take." Never scope on the spot. Panic is contagious.

𝗡𝗮𝗺𝗲 𝘁𝗵𝗲 𝘁𝗿𝗮𝗱𝗲𝗼𝗳𝗳."I can take this on. Here's what it would replace, or here's what it adds to our agreement." Make the cost visible. Let them choose.

𝗣𝘂𝘁 𝗶𝘁 𝗶𝗻 𝘄𝗿𝗶𝘁𝗶𝗻𝗴. A quick email: "Just to confirm, we're adding X to scope. This changes our timeline/fee to Y." Not legalistic. Just clear.

𝗨𝘀𝗲 𝘁𝗵𝗲 𝗰𝗼𝗻𝘁𝗿𝗮𝗰𝘁 𝗮𝘀 𝗮 𝗽𝗮𝗿𝘁𝗻𝗲𝗿, 𝗻𝗼𝘁 𝗮 𝘄𝗲𝗮𝗽𝗼𝗻. "When we scoped this, we planned for A and B. This is C. Let's figure out together how to handle it." You're solving it with them, not blocking them.

𝗧𝗵𝗲 𝗵𝗮𝗿𝗱𝗲𝘀𝘁 𝗽𝗮𝗿𝘁:  Saying "yes, and here's what that changes" when they want to hear "yes, no problem."

But every boundary you don't hold becomes a precedent.

This is the kind of thing we work through inside Fractional Institute — how to protect your practice without damaging the relationship.

Will Gould

Human+AI+Automation Org Evolution | I build revenue operating systems and teach operators the revenue architecture skills necessary to replace collapsing GTM roles.

"So what do you do?"

I used to dread this question. (nobody is worse at personal positioning that a marketer who has been doing it for others for years)

Explaining fractional leadership in a pithy, circumspect way isn't easy. 

I'd launch into fifteen years of experience. B2B marketing. Demand gen. 
Sales alignment. Built teams. Scaled programs. Worked with companies from Series A to PE rollups.

By the time I finished, their eyes had glazed over. Polite nod. Subject change.

I was answering with my resume. Not with what they actually needed to hear.

The breakthrough came when I flipped it.

Stop describing yourself. Start describing who you help and what changes for them.

Now I say:
"I help growth-stage companies figure out why their marketing and sales aren't working together—and fix it."

One sentence. They instantly know if they're the person I help or not.

The structure is simple:
"I help [specific type of company] with [specific problem] so they can [specific outcome]."

Not clever. Clear.

A few more examples:

"I help B2B SaaS companies between $5M-$20M ARR build demand gen that doesn't depend on the founder's network."

"I help PE-backed companies fix the sales and marketing handoff so deals stop dying in the middle of the funnel."

If you can't say who you help and what problem you solve in one sentence, you don't have positioning yet.

You have a resume.

And resumes don't get referrals. Clarity does.

Every week, the clock resets.

No one is checking if you were at your desk by 8am. No one noticed you worked until 10pm on Thursday. No one is tracking your PTO or asking about your Q1 goals.

No one cares.

I don't mean that harshly. I mean it literally.

As a fractional executive, there's no system holding you accountable. No boss. No standup. Just you, your clients, and the quiet weight of keeping it all moving.

The inertia required to do be a fractional executive is enormous.

Not the client work. That part's easy. 

I mean the other stuff:
Finding the next client(s) before you need one. 
Following up when you haven't heard back. 
Networking when you'd rather be out with friends. 
Turning the crank of the business when no one's watching. 
Starting over every Monday like the week before didn't count.

There's no momentum that carries you. You create the momentum. 

Every week.

So if you're reading this on a Sunday night, thinking about the week ahead, wondering if you're doing this right (as I am), you're not alone.

Every fractional I know feels this. The successful ones just keep showing up anyway.

Here's to another week of building it yourself.

I have six fractional clients, twelve standing meetings, and complete control of my week. Here's how.

Five years in, and my Tuesday still looks like chaos.

The difference is I built the chaos on purpose.

When I started, fragmentation was something that always seemed to happen to me. 

Now it's something I design.

Here's what Tuesday looks like in year five:

7am: Deep work block. No calls before 9. Non-negotiable. 
9am: Client A leadership meeting. I'm the "CMO" for the next 90 minutes. 
10:30am: Transition buffer. 15 minutes I used to skip. Now I protect it like a client meeting. 
11am: Client B call. Different company, different problems, complete context switch. 
12pm: Lunch away from the desk. Took me three years to learn this one. 
1pm: Prospect call. Capped at 45 minutes. I end it, not them. 
2:30pm: Deliverable work. Batched. No Slack, no email. 
4pm: Client A emergency lands in my inbox. I see it at 5pm. It can wait until tomorrow. 
5pm: Admin block. Invoicing, contracts, the stuff that used to slip through the cracks. 
5:30pm: Done. Actually done.

It's still fragmented. That doesn't change.

What changes is who's in control of the fragmentation.

The first few years, you're surviving the juggle.

Eventually, you realize the juggle is the job, and you either architect it intentionally or it architects you.

Three things that took me too long to figure out:
→ Buffers between clients aren't wasted time. They're the reason your 11am doesn't suffer from your 9am. 
→ Protecting deep work blocks matters more than adding another client. 
→ "Urgent" is usually someone else's failure to plan. You don't have to absorb it.

The freedom of fractional work isn't "do whatever you want."

It's "design the constraints you're willing to live inside."

If your Tuesday still feels like it's happening to you, the system needs redesigning, not more effort.

Marketing isn't a generalist's game. Especially not fractional marketing.

I learned this the hard way.

Early in my fractional career, I thought expertise was transferable. I'd spent years in mid-market B2B — $5M to $20M companies figuring out how to scale. I knew that world cold.

Then I took a client at $80M.

Same industry. Same buyer persona. Same general function.

Completely different job.

The tools were different. The team structure was different. The decision-making speed was different. The problems I was hired to solve weren't problems I'd ever actually solved.

I was learning on their dime. It didn't go well.

Here's what I've come to believe:

The growth patterns that work at $3-10M are completely different from the ones that work at $50M+.

At $3-10M, you're building the plane while flying it. Scrappy. Fast. Founder-adjacent. You're often the entire marketing function.

At $50M+, you're optimizing an existing machine. Managing managers. Navigating politics. Working through layers.

The skills don't transfer cleanly. The playbooks don't transfer at all.

And here's the part that surprises people:
Moving sideways, different industry, same company size, is easier than moving up or down within an industry you know well.

A fractional who scaled three $8M SaaS companies can probably scale an $8M services business. The context changes. The physics don't.

But a fractional who spent their career at $100M companies? Dropping into a $5M company isn't a step down. It's a different sport.

As a fractional, you're hired for fast results. There's no six-month learning curve. No training program. You're expected to know what works and do it.

That only happens if you stay in the zone where you've already done it.
Generalists get hired. Specialists get results.

Agree or disagree: sideways is easier than up or down?

If you're running a business in the $1-5M range, you probably still own revenue.

Not officially. But in practice, you're the one who knows why deals close, which channels actually work, and what to do when the pipeline gets weird.

This creates a timing problem.

Hire a CMO or CRO too early: You're paying an executive salary for someone to guess. You don't have enough signal yet to know what playbook fits. They'll build infrastructure for a business you're not sure will scale yet, and you'll rebuild it later.

Hire too late: The revenue system calcifies around you. Your workarounds become load-bearing walls. When you finally hire, it's in crisis mode, which means desperation picks and no time to onboard well.

The framework I use:
You're too early if you're hiring them to figure out what works.
You're on time if you're hiring them to scale what's already working.
You're too late if you're hiring them to fix what broke while you were busy doing everything else.

Most founders in this range aren't actually ready for a full-time executive. They're ready for architectural support, someone who can design the system, install the infrastructure, and create the conditions for that future hire to succeed.

That's a different job. Often a fractional one.

The goal isn't to delay building your revenue team. It's to stop hiring executives into a system that isn't ready to receive them.

I sold 45 hours my first month as a fractional.

Four clients. Full calendar. Finally doing the work I was good at, on my own terms.

By week three, I was underwater.

Not because the client work was hard. That part I could do.

I was drowning in everything else: 
→ Chasing the next client while serving the current ones 
→ Invoicing at 10 pm because there's no back office 
→ The 45 minutes of mental reset every time I switched contexts 
→ The thinking time that makes your advice worth paying for 
→ The recovery time that keeps you from hating all of it

Here's the math nobody tells you:
40 hours a week ≠ 40 billable hours.

It's closer to 24.

Roughly 40% of your time is the business of the business, not the billable work.

I call it the 40% problem.

And if you don't build it into your capacity math from day one, you'll spend your first year wondering why you're exhausted and underearning.

#fractionalCMO

The positioning that made you successful fractional executive might be the thing holding you back in 2026.

I've been thinking about this a lot lately.

Five years ago, I had rock solid positioning. "I help growth-stage B2B companies fix their marketing and sales alignment."

It worked. Referrals flowed. Conversations with new prospects were easy. 

But in the last couple of years, something's been slipping.

As the market has changed so has the work. I'm not just fixing marketing and sales alignment anymore. I'm redesigning how revenue systems connect-marketing, sales, ops, retention. 

I'm the person who sees across functions that don't naturally talk to each other.

The problem? My positioning still says "fractional CMO."

So I get pulled into conversations about marketing execution when the real problem is architectural. I get compared to other fractional CMOs when what I'm doing isn't really that anymore.

The clarity from years ago that got me out of the gate is now a box.
I'm hearing this from other experienced fractionals too:

→ The "fractional CRO" who's really redesigning the entire revenue operating system 
→ The "fractional CMO" who spends half their time fixing sales process gaps 
→ The "RevOps leader" who's actually the only person seeing the whole picture

The titles made sense when we started. They don't describe what we've become.

Here's the tension:

Narrow positioning makes you referable. But it also makes you legible only for the thing you used to do, not the thing you've evolved into.

I don't have this fully figured out yet. But I know the answer isn't "go broader." That's just a different trap.

The answer seems to be: position for the problem you solve at the system level, not the function you came from.

Still working on what that looks like.

If you've been at this a while, are you feeling this too? What's your positioning say versus what you actually do now?

"I'm not sure I'm doing this right." You're not alone.

I have a couple dozen conversations with people doing fractional revenue work every week.

The same themes keep coming up:

"I didn't realize how much time pipeline would take" 
"Pricing feels like guessing" 
"I miss having people to talk through problems with" 
"The context-switching is brutal" 
"I'm not sure I'm doing this right"

None of this is surprising. But it's validating to hear it's not just you.

If you're in your first year, what's been harder than you expected?

And if you're past that year, what do you wish you'd known?

The proposal review was on Monday. By Thursday, I was spiraling.

Friday morning I checked my email six times before 9am. Refreshed LinkedIn. Checked spam. Opened send receipts to make sure they were still engaging with me.

It were. They just hadn't responded.

By Friday afternoon my brain had written the whole story:

They hated the price. 
They're talking to someone else. 
I misread the conversation. 
I'm not getting this. 
I need to find three more opportunities immediately.

By Saturday I was mentally restructuring my entire pipeline, questioning my positioning, and wondering if I should lower my rates.

Monday morning they replied: "Sorry, been slammed. This looks great. Let's talk Wednesday."

All of that spiral. For nothing.

Here's what I've learned:
When your pipeline is five conversations instead of fifty, every silence feels like a signal. You overweight every deal. You live and die on each reply.

The math of fractional work makes this worse. You don't need a hundred clients. You need five or six. So when one goes quiet, it feels like 25% of your future just evaporated.

It didn't. But your nervous system doesn't know that.

What helps me now:
𝗡𝗮𝗺𝗲 𝗶𝘁. When I catch myself refreshing email, I literally say out loud: "This is the panic. It's not real information."

𝗭𝗼𝗼𝗺 𝗼𝘂𝘁. I keep a list of every time I spiraled over silence, and what actually happened. Almost always: they were just busy.

𝗞𝗲𝗲𝗽 𝗺𝗼𝘃𝗶𝗻𝗴. The spiral wants you to freeze. Actively work on your pipeline. Follow up with one dormant contact. Action breaks the loop.

𝗥𝗲𝗺𝗲𝗺𝗯𝗲𝗿 𝘄𝗵𝗮𝘁 𝘂𝘀𝘂𝗮𝗹𝗹𝘆 𝗵𝗮𝗽𝗽𝗲𝗻𝘀. Most silence isn't rejection. It's just silence. People are busy. Proposals sit in inboxes. Decisions take time.

The quiet week panic never fully goes away. You just get faster at recognizing it for what it is.

And it's almost never what you think it is.

AI is a stress test.

In companies without a system, revenue ops lives in permanent patch-and-move mode:
 
Fix the CRM.
Chase the forecast.
Patch the funnel.
React to the miss.
Repeat.

AI just makes that cycle faster.

The problem isn’t effort.
It’s the absence of an operating system for revenue.

When there’s no shared model for how demand becomes deals, and deals become decisions, every new tool adds noise instead of leverage.

The fix isn't better tools. It's a forcing function.

Before any AI implementation, answer one question: "What decision does this enable that we couldn't make before?"

If you can't answer that clearly, you're automating chaos.

CMOs get blamed and fired for systems they don’t control.

I've watched dozens of strong CMOs lose leverage with their CEOs.

Not because they got worse at marketing. 

The problem is the layer they're operating at.

When a revenue miss happens, marketing always seems to get the first call. "What's wrong with the campaigns?" "Why isn't the funnel converting?" "Can we try a different channel?"

But the actual problem is often upstream.  

Sales changed the lead scoring and never told anyone. 

Stage definitions that mean one thing in the system and another in the board meeting. 

Forecasts that extrapolate activity instead of reflecting reality.

The CMO didn't create these problems. But they absorb the blame for them. And no amount of campaign optimization fixes a system that was never designed correctly.

This is the CMO trap: high accountability, limited authority, and a scope that keeps you downstream of the decisions that actually determine outcomes.

The escape isn't more tactics. 

The escape is learning to see revenue as a system. 
To diagnose before you prescribe. 
To distinguish system failures from execution failures from authority constraints. 
To explain what's actually broken in the revenue system in a way that executives can act on, instead of producing another dashboard that gets questioned in the next QBR.

Ths is the shift from CMO to CMO + CRA capability.

It's not a new title. It's not a replacement for marketing expertise. It's the diagnostic layer that makes your experience durable as execution becomes cheap and AI accelerates activity.

If you're a CMO in 2026, it's time to stop living in systems that are stacked against your success. Learn to explain what's actually broken across all revenue domains that marketing feeds into.

If you can’t explain the revenue system, someone else eventually will.

#cmo #marketingleadership

Most fractional discovery calls fail before they start.

The fractional executive shows up trying to impress. The prospect shows up hoping to be sold.

Neither is assessing fit.

A discovery call has one purpose: figure out if you can help and if you want to.

Here's the structure I use: 30 minutes. No pitch deck.

𝗦𝗲𝘁 𝘁𝗵𝗲 𝗳𝗿𝗮𝗺𝗲 (𝟮 𝗺𝗶𝗻)
Start by telling them how this works.
"Here's how I like to use this time. I'll ask some questions to understand what's going on, then I'll tell you honestly whether I think I can help. 

This does two things: takes the sales pressure off and positions you as the one assessing them.

𝗖𝗼𝗻𝘁𝗲𝘅𝘁 (𝟱 𝗺𝗶𝗻)
"Tell me about the situation that led to this conversation."
Then stop talking.
You're listening for the real problem under the stated problem. They'll often say "we need marketing help" when the actual issue is "our sales and marketing teams blame each other and nothing converts."

𝗛𝗶𝘀𝘁𝗼𝗿𝘆 (𝟱 𝗺𝗶𝗻)
"What have you already tried?"
This tells you what's failed and why. It also prevents you from recommending something they've already done.
Follow-ups:
"What worked? What didn't?"
"Why do you think that didn't solve it?"
"Who was involved in that effort?"

𝗦𝘁𝗮𝗸𝗲𝘀 (𝟱 𝗺𝗶𝗻)
"What happens if this doesn't get solved in the next 6 months?"
Urgency lives here. No urgency, no engagement.
If they can't articulate the cost of inaction, they're not ready to hire. They might take calls forever.
Follow-ups:
"Who else is feeling the pain from this?"
"Is this a priority or a someday problem?"

𝗩𝗶𝘀𝗶𝗼𝗻 (𝟱 𝗺𝗶𝗻)
"What does success look like?"
Now you know the target. And you'll hear whether their expectations are realistic.
Follow-ups:
"How would you know it's fixed?"
"What would be different in 90 days if this worked?"
"Is there a number attached to this?"

𝗙𝗶𝘁 (𝟱 𝗺𝗶𝗻)
Finally it's your turn to talk.
If it's a fit: "Based on what you've shared, here's what I think is actually going on, and here's how I'd approach it."
Give them a taste of how you think. This is where they decide if they trust your brain.
If it's not a fit: "I don't think I'm the right person for this. Here's why, and here's who might be better."

𝗥𝗲𝗱 𝗳𝗹𝗮𝗴𝘀 𝘁𝗼 𝗹𝗶𝘀𝘁𝗲𝗻 𝗳𝗼𝗿:

Money talk before problem talk. If they're negotiating fees before they've explained the problem, budget will be a fight the whole engagement.
Vague pain, vague timeline. "We just need help with marketing" + "sometime in the next quarter" = not ready.
Blame everywhere. If the problem is everyone else's fault, you're inheriting a mess with no ownership.
Shopping for validation. They've already decided what they want. They're looking for someone to execute their bad plan.

You're not trying to win the call. You're trying to figure out if this is a client you want, solving a problem you can fix, at a price that works.
If the answer is no to any of those, the best outcome is a fast, clear no.

30% of your automation> AI> Human operations mix is askew. Here's how to tell which 30%.

Most revenue leaders ask: "How much should we automate?"

Wrong question.

The real question: "What are we automating that we shouldn't? And what are we doing manually that's already commoditized?"

The anxiety I'm seeing:
→ "We invested $200K in AI sales tools. Did we jump too early?"
 → "My competitor automates their SDR function. Should we?"
 → "We manually review every proposal. Are we dinosaurs?"
 → "AI can do X now. Should we fire our team doing X?"

Leaders are paralyzed between moving too slow (falling behind) and too fast (deploying AI that breaks things).

The issue isn't speed. It's category confusion.

Four categories most organizations mix up:
🟢 COMMODITIZED – Fully automated. If you're doing this manually, you're burning money.
🔵 DEPLOYING AT SCALE – AI-assisted with governance. Companies figuring out boundaries.
🟠 EMERGING – Early adoption. High variance. Some winning, most experimenting.
🔴 HUMAN REQUIRED – Still needs humans. Not capability limits—accountability.

The mistake I see repeatedly:

Companies deploy "Emerging" AI (proposal generation) while still manually doing "Commoditized" work (lead routing). That's backwards.

Or they automate something that should stay "Human Required" (forecast commits) and wonder why their forecasts got worse.

The right approach:
Audit your current state - Where are you spending human time on commoditized work?
Identify the gap – What's deploying at scale in your industry that you're not using?
Experiment carefully – Test emerging tech, but with boundaries and validation.
Protect the human layer – Some things should stay manual. That's strategy, not weakness.

I mapped this across Marketing, Sales, Customer Success, and AI systems. The results are... revealing.

(See graphics attached)

What I learned:
Most companies have ~30% of their revenue operations in the wrong category. They're either:

Automating things that require judgment (and creating chaos)

Manually doing things that should have been automated years ago (burning budget)

Treating "Emerging" AI like it's "Commoditized" (deploying without governance)

The winners aren't automating more. They're architecting better boundaries.
They know what to commoditize, what to pilot, and, most importantly, what to protect.

If your mental model of "what can be automated" is more than 6 months old, it's already outdated. The landscape shifted. Again.

The question isn't "are we behind?" The question is: "Do we know where to draw the lines?"

What category confusion are you seeing in your revenue operations?

You've tried fixing this before.

The CRM and automation upgrades were supposed to create visibility. The sales consultant who fired everyone up for two weeks. The marketing agency that promised leads. The RevOps hire who built dashboards nobody looks at.

Each one made sense to you on that Zoom call. Each one “solved” a piece of the problem. None of them fixed it.

And today, someone new is in your inbox promising they can help.

Sooo, why would this time be different?

Here's what I've learned after 10+ years inside companies like yours: most solutions fail because they treat symptoms, not the system.

You don't have a CRM problem. You don't have a marketing problem. You don't have a sales problem.

You have an architecture problem. Hard stop. 

You have a revenue system that was never designed. It just... accumulated. 

Every tool, every hire, every process was added to fix the last thing that broke. Nobody ever stepped back to see if they fit together.

That's why the CRM didn't help. It was a good tool dropped into a broken system.

That's why the agency didn't deliver. They drove leads into a handoff that was already leaking.

That's why the dashboards collect dust. They're measuring a machine that doesn't work.

So, before you try another tool, consultant, AI solution, it's worth understanding why the last five didn't stick. The answer usually isn't that they were bad. 

It's that nothing underneath them had changed.

Nobody is going to tap you on the shoulder and tell you it's time.

No boss is going to say "you've outgrown this." No client is going to appear and make the leap feel safe.

Going fractional is a decision you make without permission. That's exactly what makes it hard.

You've built real expertise. Delivered real results. But the jump still feels like risk because it is.

So you wait. For more savings. More clarity. More proof it'll work.

But here's what nobody tells you: The clarity comes after the jump, not before.

Every fractional leader you admire made the decision while uncertain. 

They just decided that uncertainty was better than another year of the same ceiling.

You're not waiting for readiness. You're waiting for a guarantee that doesn't exist.

The only question is whether 2026 is the year you stop negotiating with yourself, or another year of almost.

#fractionalCMO #marketingleadership

The Expectation Gap

I spent fifteen years inside companies and agencies. Titles, teams, budgets, the whole thing.

When I went fractional, I assumed the hard part was behind me. I knew how to do the work. How hard could the rest be?

That first year nearly broke me.

Not because the client work was hard. I could do that with my eyes closed.

What broke me was everything else:

Selling when I'd never had to sell myself before

Pricing when I had no idea what I was worth outside a salary

Managing three clients who all thought they were my only priority

The silence of working alone after years of teams was deafening

The work wasn't the problem. The business of the work was the problem.

Nobody told me that being good at the work and being good at running a practice are two completely different skills.

If you're making this transition, or thinking about it, that's the gap to prepare for.

The expertise gets you in the door. Everything else determines whether you stay.

The thing that surprised me most about going fractional:

It wasn't the sales. Wasn't the pricing. Wasn't even the context-switching.

It was the loneliness.

Not "I need friends" loneliness. A different kind.

The loneliness of making a big call with no one to gut-check it.

Of carrying a problem I couldn't share with the client, because they were the problem.

Of landing a win and having no team to celebrate with. Just me, my laptop, and a Slack emoji from someone who'd moved on to the next thing.

Of having fifteen years of expertise and no one to develop with it.

Inside a company, you're surrounded by people who share your context. They know the politics, the history, the stakes. You can say "can you believe what happened in that meeting?" and someone knows exactly what you mean.

As a fractional, you're always a little bit outside. Even when you're embedded. Even when they call you "part of the team."

I didn't expect this to be the hard part. But it was.

The fix wasn't to push through it. It was to stop pretending it wasn't there.

I built the support structures I was missing, peers who do this work, people I can call when I'm stuck, a community that shares the context my clients can't.

The fractionals who thrive don't white-knuckle it alone.

#fractionalCMO

I made my audit shorter, more expensive, and less comprehensive. It works better now.

My audit (diagnostic, assessment) offer used to close at 54%. Last year it bottomed out at 25%.

Same offer. Same price. Same pitch. 

I've had my head in the sand for the past couple of years not wanting to believe that the market had moved on from what I was offering.

Here's what I figured out. And, what I changed.

What broke:
Four years ago, "let me assess your situation" was enough. Companies were buying diagnostics because they didn't know what they didn't know.

Now? Everyone's been diagnosed. They've had consultants in. They've done the audits. They've seen the decks.

"I'll tell you what's wrong" isn't a value prop anymore. It's noise.

What I changed:

Old audit: "I'll assess your marketing and sales alignment and deliver a report with recommendations."

New diagnostic: "I'll find the three deals you should have closed last quarter and show you exactly where they died. Then we'll fix the first one together."

Same duration. Same price. Completely different energy.

The shift: → From "I'll observe and report" to "I'll find something specific and we'll fix it" → From comprehensive to precise → From recommendations to outcomes.

The details that matter:
Duration: Still 2-3 weeks. Didn't change.

Price: Actually raised it. $4,500 → $6,000. The specificity justified the increase.

Deliverable: No more 20-page decks. One working session, one fixed problem, one clear decision on whether to continue.

Conversion to implementation: Back up to 53%. Not because I'm selling harder. Because they've already experienced the work.

What I learned:
The audit isn't a discovery phase. It's a proof of concept.

If they don't feel something shift during the audit, they won't buy the implementation. No matter how good your report is.

The other two offers (implementation and advisory) needed tuning too, but fixing the diagnostic fixed the whole pipeline.

The question for you: If your entry offer isn't converting like it used to, it might not be your sales skills.

It might be that the market moved and the offer didn't.

When's the last time you rebuilt your diagnostic from scratch?

Everyone tells you to ditch hourly pricing. Retainers are better. Value-based is the goal. Hourly is for beginners.

I've been doing this for years. I still use hourly for one specific situation.

And it's the most profitable part of my practice.

𝗧𝗵𝗲 𝘀𝗶𝘁𝘂𝗮𝘁𝗶𝗼𝗻: 𝗔𝗱𝘃𝗶𝘀𝗼𝗿𝘆 𝗿𝗲𝗹𝗮𝘁𝗶𝗼𝗻𝘀𝗵𝗶𝗽𝘀.

Two to four hours a month. No deliverables. No projects. Pure strategic access.

A CEO texts me a question about their revenue process. We jump on a call for 45 minutes. I send a follow-up with three things to try. Done.

No scope document. No retainer negotiation. No monthly check-ins to justify the fee.

Just: "I need your brain for an hour. What do you charge?"

𝗪𝗵𝘆 𝗵𝗼𝘂𝗿𝗹𝘆 𝘄𝗼𝗿𝗸𝘀 𝗵𝗲𝗿𝗲:
𝗧𝗵𝗲𝗿𝗲'𝘀 𝗻𝗼𝘁𝗵𝗶𝗻𝗴 𝘁𝗼 𝘀𝗰𝗼𝗽𝗲 𝗰𝗿𝗲𝗲𝗽 𝗶𝗻𝘁𝗼.

Retainers fail when the work expands beyond what you quoted. 

Advisory has no deliverables to expand. They're buying access to thinking, not output.

𝗧𝗿𝗮𝗰𝗸𝗶𝗻𝗴 𝗵𝗼𝘂𝗿𝘀 𝗽𝗿𝗼𝘁𝗲𝗰𝘁𝘀 𝗯𝗼𝘁𝗵 𝗼𝗳 𝘂𝘀.

They know exactly what they're paying for. I know exactly what I'm giving. No ambiguity, no resentment.

𝗧𝗵𝗲 𝗿𝗮𝘁𝗲 𝗰𝗮𝗻 𝗯𝗲 𝗵𝗶𝗴𝗵𝗲𝗿 𝘁𝗵𝗮𝗻 𝘆𝗼𝘂 𝘁𝗵𝗶𝗻𝗸.
My advisory rate is $500/hour. Two-hour minimum.

Sounds aggressive. But for a CEO who needs a quick answer from someone who's seen their problem fifty times? It's cheap compared to hiring a consultant for a full engagement.

𝗜𝘁 𝗳𝗶𝗹𝘁𝗲𝗿𝘀 𝗳𝗼𝗿 𝘁𝗵𝗲 𝗿𝗶𝗴𝗵𝘁 𝗰𝗹𝗶𝗲𝗻𝘁𝘀.
The people who balk at $500/hour for advisory aren't my clients. The people who don't blink are exactly who I want to work with: decisive, value-focused, no hand-holding.

𝗪𝗵𝗲𝗿𝗲 𝗵𝗼𝘂𝗿𝗹𝘆 𝗱𝗼𝗲𝘀𝗻'𝘁 𝘄𝗼𝗿𝗸:
Implementation. Projects. Anything with a deliverable.

The moment there's a "thing" you're building, hourly turns into a negotiation about how long the thing should take. You either pad your estimate (and feel dishonest) or scope it tight (and eat the overruns).

Retainers and project fees work better there.

The nuance nobody talks about: Pricing models aren't religion. They're tools.

Hourly isn't "bad." It's bad for certain work. For advisory? It's clean, simple, and lucrative.

The goal shouldn't be to eliminate hourly from your practice. It's to know when it serves you and when it doesn't.

𝗠𝘆 𝗰𝘂𝗿𝗿𝗲𝗻𝘁 𝗺𝗶𝘅:
𝗜𝗺𝗽𝗹𝗲𝗺𝗲𝗻𝘁𝗮𝘁𝗶𝗼𝗻 𝘄𝗼𝗿𝗸: Monthly retainer, clear scope, day rate for overflow
𝗗𝗶𝗮𝗴𝗻𝗼𝘀𝘁𝗶𝗰𝘀: Fixed project fee
𝗔𝗱𝘃𝗶𝘀𝗼𝗿𝘆: Hourly, $500/hr, two-hour minimum

Three models. Three purposes. All working together.

What's your mix?

#fractionalCMO

Cynthia O'Connor

Everlaw

Senior Enterprise Account Executive

Prokeep

Prokeep is the leading customer experience management software for wholesale distributors.

Account Executive

Boost Labs

Boost Labs has expertise in new cutting-edge AI services designed to drive your business forward.

Enterprise Sales Executive

Sitecore

Senior Account Executive - Professional Services

Hedgehog Development acquired by Sitecore

Hedgehog is a full service digital agency leveraging deep technical expertise to deliver sophisticated web experiences.

Senior Account Executive

Innovolt

Enterprise Account Executive

Sprint

Solution Sales Engineer

Sales Manager

Senior Sales Executive/Team Leader for Nextel a New Telecom offering

Sales Team Leader/Senior Account Executive

Passionate About Problem Solving, Sales and Client Success Obsessed, and Connoisseur of TV Cooking Shows

Watching my father live his passion for helping others as a Middle School Science Teacher and Volunteer Fire Chief in our community, I have mirrored my career to help others through sales. 

Embracing my client's goals and providing direct communication and transparency, which leads to productive engagements -together we are aligning them with the best solution and delivering key outcomes. 

I am blessed with two great kids and spend most of my free time supporting their endeavors and entertaining my two Boston Terriers.

“Integrity is telling myself the truth. Honesty is telling the truth to other people.”—Spencer Johnson

We Are Data Story Tellers

We solve data challenges for organizations that struggle to communicate their data value. We partner with data-focused customers to build data analytics products that are innovative, scalable, and platform agnostic.  Over the years our continued partnership with extraordinary customers has led us to endless successful product launches that produced real return on investment (ROI), implemented compliance, and more.

We attack each project head on and analyze your data and processes in partnership with you, learning all we can about your goals. Utilizing lean startup methodologies, we then craft an architecture that can support your dreams of greatness and combine this with incomparable elegance in design, developing technologies that help you learn from your data and share it with others in whatever platforms make the most sense. The solutions we deploy are precise and built to exacting standards.

taplio

The Battle

Will G.

Cynthia O'Connor

Followers

Posts

Engagements

Likes

Performance ScoreWill G.'s LinkedIn Performance

Ready to grow your LinkedIn presence?

taplio

The Battle

Will G.

Cynthia O'Connor

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Will G.'s LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScoreWill G.'s LinkedIn Performance