CMO+

Dynamic Fractional CMO/CRO with a proven track record in early-stage growth, specializing in scaling companies from $3-10MM to $10-30MM in annual revenue. I focus on building robust revenue operations, strategic marketing frameworks, and sustainable growth plans that align with a company’s unique trajectory. With hands-on leadership and a data-driven approach, I work alongside founders and teams to optimize processes, refine brand messaging, and expand market share.

Fractional CMO

V&L Growth Labs

-  Accelerating the growth of the consumer business through both direct digital sales & sales enablement across a network of franchise partners.
 - Building and leading an integrated marketing function encompassing both the B2B side of the business as well as the fast-growing D2C side.
 -Championing a customer-centric culture, team & attitude infused with digital and retail (or local) agility.

Partner

Brand Buddha

Lead management, account, and development teams through significant growth at a leading brand & creative marketing agency

* Manage 20+ account managers, designers, and developers 
* Promote and train four department directors 
* Manage a diverse roster of healthcare, pharma, biotech, and MedTech clients  
* Architected a company restructure resulting in a dramatic and qualifiable increase in ARR profit 
* Design and roll out a new project management department/system 
* Develop key accountabilities and responsibilities for all roles 
* Oversee talent acquisition, assessment, and placement of local and independent contractors

President - Chief Strategy Officer

Leveraged core advertising planning skills and experience to define and transform brands. Worked with clients to define brand goals, brief creative, and develop strategies based on consumer insights, trend analysis, and business objectives.  Led consumer research and insight development, bringing qual and quant together in collaboration with data analysts. Worked in concert with clients to provide strategic direction across the brand’s ecosystem (web, email, social, mobile, retail, activations, etc.).Lead client stakeholder meetings and workshops. Led team developing research including competitive analysis, emerging opportunities, and consumer insights. Provided strategic guidance on emerging media channels and platforms.

Vice President Brand Management & Strategy

Responsible for leading and executing strategic planning and business development functions for Brand Buddha. Serves as the primary strategy resource for Brand Buddha clients, and has oversight for relationship development, network development, strategic evaluation of business plans, affiliations, joint ventures, acquisitions and marketing.

Vice President Of Business Development

ConstantPLAN - (acquired August 2016)

ConstantPLAN is a wall-to-wall marketing and media organization focused on creating brands for individual business professionals. ConstantPLAN's methodology creates strong, hyper-local brands for advisors, consultants, attorneys, and professionals in the advice business.

Senior Vice President Marketing

PointServ

Developed and implemented sales forecasting, planning, and budgeting processes. Establishes high levels of quality, accuracy, and process consistency in planning, forecasting, and budgeting approaches used by the sales organization.

Developed and administer and compensation, commission plans and incentive development and tracking. 

Created company-wide sales plan. Prepares forecasts, including significant input into strategic planning and the direction of the PointServ.

Developed company-wide training systems designed to raise sales performance against plan for all aspects of the sales group across a variety of key performance metrics. Implements metrics to generate data and tracking for decision making.

Currently providing knowledge and experience-based leadership to PointServ (particularly Sales, Finance and Marketing) to guide effective decision-making and continuous improvement.

Vice President - Sales & Marketing

Valentine & Lewis

As VP of Institutional Accounts my daily efforts are to lead new account acquisition of multi-channel financial services product platform, and to foster working C-level professional relationships. Strategically, my responsibilities are to create organic leads of targeted prospects, to score potential relationships for profitability and to oversee the multi-stage sales process for all prospective C-level relationships.

A leader in delivering corporate and "accredited investor" solutions, V&L Institutional Services mission is to empower corporate officers with the most effective cash management, investment philosophy, key personnel retention strategies, and HR retirement platforms they require, in order to optimize their financial needs and meet their business strategy.

V&L Institutional Services is changing how "accredited" investors approach the Reg D marketplace by combining high altitude analytics with performance predictive capabilities.

VP of Institutional Accounts

Raymond James Financial Inc.

•Effectively managed expansion and business operations for the Western Region
•Energized Defined Contributions (DC) & Defined Benefit (DB) business through approximately three new market territories in the Southwest resulting in 34 new corporate relationships.
•Delivered effective plan selection and employee education for corporations, institutions, foundations, and accredited individuals
•Actively managed dynamic pooled asset accounts
•Presented retirement sales training and market updates relating to best practices for DB, DC, NQDC, etc. plans.

Vice President, Private Wealth Management 

Associate Vice President

Prudential Financial (previously Prudential Securities)

Financial Advisor

Terminix

Vice President Direct Sales

You are a founder. A CEO. An Entrepreneur. What you know about marketing, sales, and revenue operations has taken your company as far as it can.  

You likely have a couple of entry/mid-level marketers or a consultant or two on your payroll. You know marketing, sales, and revenue operations are evolving rapidly due to AI systems. You know you need to do something now. 

That is where I come in.

I work with startup founders (seed to series B) to turn their vision into actionable strategy, systems, and execution that attracts the right eyeballs, engages, and converts new business to scale your revenue operations. 

𝐇𝐞𝐫𝐞’𝐬 𝐡𝐨𝐰 𝐢𝐭 𝐰𝐨𝐫𝐤𝐬. 3-6 𝐦𝐨𝐧𝐭𝐡 𝐞𝐧𝐠𝐚𝐠𝐞𝐦𝐞𝐧𝐭𝐬

In the past 24 months, I’ve scaled 8 startups from $8MM ARR to $49MM by fixing one thing: The math behind growth.

𝐌𝐲 𝐀𝐩𝐩𝐫𝐨𝐚𝐜𝐡:

𝐀𝐈 𝐓𝐡𝐚𝐭 𝐏𝐫𝐢𝐧𝐭𝐬 𝐏𝐢𝐩𝐞𝐥𝐢𝐧𝐞: The systems I employ slash CAC by 40%* in 90 days (no, that’s not a typo).
𝐏𝐥𝐮𝐠-𝐚𝐧𝐝-𝐏𝐥𝐚𝐲 𝐒𝐜𝐚𝐥𝐢𝐧𝐠: Done-for-you frameworks for messaging, ads, and lead gen—no “strategy debt.”
𝐙𝐞𝐫𝐨 𝐕𝐚𝐧𝐢𝐭𝐲 𝐌𝐞𝐭𝐫𝐢𝐜𝐬: I obsess over revenue, not likes or clicks.

𝐇𝐨𝐰 𝐈𝐭 𝐖𝐨𝐫𝐤𝐬 (3-6 𝐌𝐨𝐧𝐭𝐡𝐬 𝐭𝐨 𝐏𝐫𝐞𝐝𝐢𝐜𝐭𝐚𝐛𝐥𝐞 𝐆𝐫𝐨𝐰𝐭𝐡)

𝐆𝐫𝐨𝐰𝐭𝐡 𝐀𝐮𝐭𝐨𝐩𝐬𝐲: I reverse-engineer your funnel to find where $$ bleeds (spoiler: it’s usually attribution).
𝐀𝐈 𝐎𝐯𝐞𝐫𝐡𝐚𝐮𝐥: Deploy tested systems to hyper-target high-LTV customers (not just “more traffic”).
𝐒𝐜𝐚𝐥𝐞 𝐨𝐧 𝐀𝐮𝐭𝐨𝐩𝐢𝐥𝐨𝐭: Train your team to run the machine—so you don’t need me forever.

Getting beyond $5M ARR isn’t luck. 

𝐋𝐞𝐭’𝐬 𝐅𝐢𝐱 𝐘𝐨𝐮𝐫 𝐌𝐚𝐭𝐡:
I only take 3 clients per quarter. DM me today.

If you’re a founder building something real - and ready to scale, let’s talk.

Will G.

Most SMBs don’t have a marketing problem.
They have a systems problem.

Leads slip through cracks.
Follow-up is slow.
Tools don’t talk to each other.
Teams are drowning in manual work.
Founders can’t see what’s working and what isn’t.

Marketing feels chaotic because the system underneath it is broken.

Fix the system → marketing works.
Fix the system → sales accelerates.
Fix the system → your team stops drowning.

If you want clarity, I’m running a handful of 15-minute Revenue Systems Audits this week.

DM me AUDIT and I’ll send you the info.

Will Gould

Author of The Chief Revenue Architect. I build AI-driven revenue operating systems for SMBs (AA+OS) and teach operators the architecture skills replacing collapsing GTM roles. Fractional CMO/CRO

10 Parts of the Sales Process You Can Automate Right Now (And the 3 You Should Never Touch)

Most founders think automation is a nice-to-have.

Operators think automation is risky.

Revenue teams think automation replaces their jobs.

They’re all wrong.

Automation replaces tasks, not people.

But, only if you know where to apply it.
Here are the 10 sales workflows that should have already been automated:

Lead capture
Lead routing
Form enrichment
First-touch email
Meeting scheduling
No-show sequences
Proposal follow-ups
Stalled deal nudges
Basic qualification
CRM hygiene updates

These are pure friction.
No one builds a career repeating them.
But here are the 3 parts of sales you should never automate:

Discovery
Diagnosis
Decisions

These require judgment, the one asset AI can’t replicate.
If you automate the wrong layer, you lose revenue.
If you automate the right one, you gain speed.

The companies that win the next decade won’t out-sell their competitors.

They’ll out-system them.

McKinsey just published their 2025 AI Impact On Business Report - 10 Ways AI Just Quietly Rewrote Sales, Marketing & RevOps (And Most Teams Haven’t Noticed Yet)

McKinsey’s newest AI report makes it painfully clear,  the real shift in sales, marketing, and RevOps already happened, and most teams are still acting like it’s 2019.

AI is collapsing the operator layer
McKinsey’s data shows companies are automating the repetitive middle.
That “operator” tier in Sales/Marketing/RevOps? It’s disappearing fast.

The highest-performing companies are building AI-first systems
Not tools.  Not experiments.  Systems.

Pipeline forecasting is becoming a machine task
Operators aren’t losing their jobs to AI,  they’re losing them to math.

Buyer journey orchestration is now real-time.  AI-driven micro-coordination is replacing human follow-up.

Content is infinite,  differentiation is not
AI leveled the production playing field.  The new advantage is structural clarity: messaging frameworks, segmentation logic, and lifecycle architecture.

CAC drops when systems, not people, run touchpoints
McKinsey notes AI’s biggest benefits are efficiency and personalization.

Data governance moved from “IT task” to “RevOps survival skill”
AI breaks when data breaks. Most companies still have duct-taped systems and ungoverned lifecycle logic.

Sales productivity gains are coming from agents, not reps
McKinsey highlights the rise of agentic systems.  One strategic leader managing dozens of agents is not sci-fi,  it’s the next org chart.

Cross-functional silos are now pure revenue leakage 
AI requires end-to-end flow, not departmental borders.

The only irreplaceable role is the one designing the system
This is the entire thesis of The Chief Revenue Architect:
AI isn’t making humans obsolete.  It’s making the wrong humans obsolete.

Open article: The state of AI in 2025: Agents, innovation, and transformation by mckinsey.com

The state of AI in 2025: Agents, innovation, and transformation

Most GTM teams have three layers:
• Strategy
• Execution
• The operators in the middle holding everything together

Guess which layer AI is swallowing?
Not strategy.
Not leadership.
The middle.

Operators feel it first because they’re the ones doing:
admin work
workaround work
duct-tape fixes
cross-team logistics
manual data stitching
“who owns this?” cleanups

AI removes those tasks faster than leaders can rewrite job descriptions.
This isn’t replacing people.

It’s replacing the part of every job no one actually wanted.

But here’s the twist:

The people who understand the whole system, not just their task, become more valuable than ever.

There's a new leadership postion emerging...The Chief Revenue Architect.

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.

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Will G.

Cynthia O'Connor

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