AI Strategy Workshops and Fractional Executive Support

AI Strategy Workshop for Marketing & Sales Teams

With Support of Fractional AI, Automation & Data Executives to Support Success at Scale

A facilitated AI strategy workshop for Sales and Marketing Automation is designed for B2B companies that want to build more mature marketing automation and sales enablement across both the buyer and customer lifecycle.  Participants arrive with a completed Gabriel Sales’ Automation & Sales Enablement Maturity Benchmark™ and a completed AI Data Readiness Audit so the two to three day working session is spent making informed decisions to align sales and marketing around AI activations that scale. We rank AI use cases across multiple stages of the buyer an customer lifecycle, sequence them against what your data supports, and deliver framed projects with a phased road map and named owners.

The Challenge

Everyone wants to deploy AI and Automations at Scale. Many leadership teams don’t have the time to align around the order and expected return of deployments.

The top questions we hear from leaders who have already completed the diagnostic work:

“We have budget for AI this year and a list of twenty ideas. We don’t know the order for deployments.”

“We know our data has gaps. Nobody can tell us which gaps are blocking the things we want to do.”

“Our people are already using AI. We have no idea what they are using, or what data they are putting into it.”

“Marketing wants AI for content. Sales wants it for prospecting. IT wants to know who is accountable.”

“Our Salesforce rep says Agentforce solves this. Should we use Claude instead?”

“Everyone’s offering us free pilots and we don’t want to waste our time and give them access to our data.”

“We know how to use AI for GTM.  Can AI help us grow the customers we already have.”

We’re spending on AI and can’t show the board what is bought and when we’ll turn an ROI”

Your marketers work with a chat window open all day.  Your sales managers are running half a dozen free pilots nobody reviewed. Four new vendors are offering another four new pilots this quarter. Salesforce keeps giving you more free licenses.  None of it governed, none of it measured, and none of it sequenced against what your data supports.  Your pilots that work aren’t scaled, and the pilots that fail can’t be explained.

It’s overwhelming. Your Marketing organization knows AI and automation can transform campaigns and content production. Sales knows Claude and AI accelerates what a rep produces. IT is correct that nobody has addressed all the governance questions.   You think Agentforce can automate multiple processes with clean data and whoever asked whether you should use Claude, Co-Pilot or ChatGPT instead may be asking the right questions.  And your CFO feels the pressure of next year’s budget and explaining the ROI of all of it to the board.

AI has been deployed and its producing varied results, but your team now has a mandate/desire to deploy AI, automation and sales enablement tools systematically. And while you are waiting to get aligned and organized around a collective strategy your teams are using AI without a policy and/or with without a plan putting your budget and organization at risk using whatever tools and data they have access to.

8 out of 10 employees use unauthorized AI tools at work. 68% of security leaders, including CISOs, admit to using unapproved AI in their own daily workflows and 41% of employees find a way around application blocking.  Source:  UpGuard Survey, “The State of Shadow AI”

 Everyone is using AI. Very few have decided where it goes to work at scale and what the return on investment needs to be. That gap between knowing, deciding, forecasting and scaling are the gaps this workshop closes.

High-growth B2B companies are 3x more likely to have raised AI spending by double digits this year (71% versus 25%) and nearly 3x more likely to have fundamentally redesigned workflows around AI.  Yet fewer than 10% of organizations have scaled AI in any given function. (McKinsey, “The future of B2B sales: How growth champions rewire their playbooks with AI,” 2026 B2B Pulse Survey)

What Areas Does The Workshop Address

Automation is not new.  Automation with AI is. An AI and Automation strategy workshop from Gabriel Sales is a facilitated two to three day onsite working session, not a presentation. Your leaders do the deciding; we bring the structure, the learnings from your Data Hygiene and Readiness Audit, the proven AI / Data Science expertise and the technical experience required to help your team make the right decisions for your organization.

Where it Lands: Ideal Customer Profile (ICP) and behavioral segmentation, content and campaign production, predictive lead scoring, next-best-content, journey personalization, campaign performance analysis. Unbiased Marketing Cloud Next, Data360, Claude & Snowflake advice. 

Where it Lands: Prospect research, prioritized lead lists, call and email drafting, next-best-action, Aligned ABM strategies & workflows, forecasting, Claude, CoPillot,, Agentforce & Einstein agents working inside Sales Cloud. 

Where it Lands: Onboarding and adoption nurturing, health and churn signals, renewal risk, upsell and cross-sell triggers, advocacy and referral programs, service-to-sales hand-offs.

Where it Lands:  The findings from your audit executed prior to the workshop are mapped use case by use case so you understand what can be done immediately, what needs to be fixed with timelines. 

Tracks 1, 2 and 3 are the onsite business sessions. 

In most AI workshops the data conversation is speculative.  Not ours.  Because we will have run the Data Audit prior to the event. After the onsite we finalize Track 4 against your selected pilots, budget and plan. 

What Happens Before the Workshop 

Two things need to happen before we schedule the workshop

There are two things we need to complete before we schedule the workshop to ensure it’s worth leaderships time. 

Why. We score your current system’s health and score your current level of automations, sales enablement and sales & marketing connectivity and alignment. Its the sequencing instrument for smart and viable recommendations. 

Why. We examine thresholds, sync and duplicate integrity, enrichment coverage, governance, and what your records can and cannot ground an AI model on. It is the feasibility instrument that turns “can we do this?” from an argument into a scored answer before anyone books a flight.  Then on Day 1 of the workshop it allows us to tell you which of your ambitions viable vs. aspirational

Why. These services provide sales and marketing teams jump starts on increased maturity and sales enablement in the short term while simultaneously prepare for the foundational readiness for AI at scale.  It also gives Gabriel Sales a deeper understanding of how your frontline users run marketing and sales processes and campaigns.

If you have not done either of these you can get started with your Start with the free Salesforce Technology Health Check. It costs nothing to take this first step.  And all Health Check come with your Gabriel Sales Automation & Sales Enablement Maturity Matrix™ Benchmark with no future obligations. 

The rest of the preparation start three to four weeks prior

A stakeholder survey to every participant: Current priorities, biggest time sinks, what they have already tried with AI, and what they believe the technology can and cannot do for their function.

Selected one-to-one conversations: Wherever the survey surfaces something worth going deeper on usually the Salesforce owner, one sales leader and one marketing leader.

A pre-read education package: Covering how AI is being applied by B2B revenue teams: How it fits across the stack, and what the Health Check, Data Audit and Benchmark findings mean in plain language for people who will not read a technical assessment.

A working session between our data lead and yours: To turn the audit into a shared, agreed statement of what is possible today so the workshop group starts from one version of the facts.

Workshop Formats (two options) and What Your Team Gets

We run two or three day workshops. Both with the end goal of aligning your Marketing and Sales Leadership and Technical teams around viable AI deployments that can scale.  

1. Define & Decide – Two-day workshop

2. Commit, Scope & Budget – Add third day

Define & Decide Workshop 

Day One – We define and discuss all the possibilities and rank

A shared read out of Maturity Benchmark, Data and other Audit findings.  A short baseline session on what AI and Automations can be leveraged on the sales and marketing tech stack. Then a session across Track 1,2 and/or 3 to understand how processes run today and what better looks like. How processes run today, what better looks like.  You exit the day with your teams ranked list of processes/initiatives.  

Day Two – We decide what makes the most sense across the organization based on viability and value

Gabriel Sales returns with preliminary data viability, data remediation and/or tech stack remediation, rough time line, AI technology and rough budget for each process.  We then walk facilitate a final decision and you exit the day with two to three viable pilots and where they will place you on the Maturity Matrix.

What Your Team Gets / Deliverable (within one week)

• Ranked list (immediately)
• An executive one-pager for each of the two to three initiative pilot you have decided to execute: Document will includes: the problem it solves, what it takes to implement, what it is worth, what it depends on for success, and who owns it.
• The data remediation and AI enablement sequence: the specific data, governance and technology repairs, the remediation and preliminary process work each initiative requires before it can run at scale. (This information is drawn directly from your audit findings and ordered by dependency and sequence)
• Resource and ownership alignment: What Gabriel Sales can provide and who does what on both sides (your org and ours).

Commit, Scope & Budget

Day Three – We dig into the two to three pilots, Leaders commit to projects, and then Gabriel Sales crafts the plan.

An optional/final one-day session where we work with your team to provide fully scoped 90 to 180 day plan against the two to three pilots, we clearly define business value, objectives, data requirements, success metrics. Post the workshop we provide Board and CFO ready documents including a rough draft preliminary budget, ROI forecasts and final project plan.

What Your Team Gets / Deliverable (within three weeks)

• The phase-one pilot definition: scope, data requirements, success measures and review cadence.
• The phased implementation roadmap: Sequenced through the stages of the Gabriel Sales Automation & Sales Enablement Maturity Matrix™, with your current stage, your target stage, and what moves you between them.
• Budget & Project Plan
• Rough draft Board Ready presentation: To support and justify budget allocation.

What Happens After the Workshop

Your team has multiple options.  You can execute on your own.  Execute specific parts with us.  Or run the entire set of AI innovations with a retained Managed Services Engagement,  Including the ongoing support of a Fractional Automation, Sales Enablement & AI Executive.  

The Fractional Automation, AI & Sales Enablement Support Executive

What Is a Fractional AI and Automation Executive?

A Fractional Automation, AI & Sales Enablement Executive is a part-time senior leader from Gabriel Sales who supports both the Sales and Marketing Leadership Team.  They steward the AI, automations, technology optimizations and data processes required for aligned sales and marketing success.  They focus on the details that often slip when innovating across multiple teams.

The six jobs this role focuses on

Strengthen the nurture-to-close engine. Helps leverage AI and technology to create great sales and customer experiences after the initial lead has been generated. Focuses on aligned sales and marketing processes and maximizing technology to increase productivity across the entire buyer journey. 

Build and hold the marketing ↔ sales bridge. Owns the hand-off, the feedback loops, shared definitions and trusted data, so both teams align around one customer experience.

Continued research and education. Stays current with emerging AI capabilities and/or researches tools you would like to explore for relevance and application so your team remains current and informed.

Stewards AI and Data Readiness. Turns the workshop, projects and prioritized roadmap into a sequenced program with owners, guardrails and measurement.

Manages Adoption & Training. Ensures the right training and support is in place for the right professionals because technology and AI without purpose and adoption is just overhead.

Ensures AI is oroducing with ROI you can measure:  Most Marketing and Sales Leaders already have enough on their plate.  A fractional AI executive helps you maximize your P&L and to share that success with your Board.

31% of Chief Sales Officers name difficulty proving the ROI of AI-driven tools as a top challenge for meeting their 2026 objectives. (Gartner Sales Survey, May 2026)

What AI, Automation and Data stewardship looks like day to day

The technology and AI decision is one to three weeks of work. The stewardship is the year that follows.

Project management. Including the data prep, governance and tech stack optimization and process work that has to land before each initiative can run, managed as a program with dates rather than as a backlog.

Tracks results. Keeps track of ROI so the investment can be defended, altered or reallocated based on ROI and strategic goals.

Guardrails and review standards for agents and prompts. What an AI agent is permitted to do inside your tech stack without a human.

88% of data and analytics leaders agree AI demands entirely new approaches to governance and security. (Salesforce, State of Data and Analytics)

Adoption and Training.  Ensures end users are trained to use the tools you invested in.

Builds toward full customer life-cycle automation. Extends automation and workflows deeper into the customer journey. 

Quarterly and/or semi-annual reviews and a re-benchmark on the Maturity Matrix™.  To support informed decisions and next step recommendations including unbiased measurement of tools and pilots.

45% of martech leaders say vendor-offered AI agents fail to meet expectations of promised business performance. (Gartner, October 2025)

Where this role fits

Out of Scope (a separate function)

Go-to-market strategy · initial awareness/demand generation and top-of-funnel lead creation · brand · media and ad buying · PR · enterprise-wide AI policy outside the revenue engine.  We have managed and can support and integrate with these these processes. Most companies we work with have the CROs, CMOs + Brand, content experts, existing Agency Partners and initial AI deployments/vendors to support GTM and lead gen. Our focus is a seamless and powerful buyer and customer after the lead has been generated.

FAQs

AI Strategy Workshops and Fractional Executive Support

What is an AI strategy workshop?

An AI strategy workshop is a facilitated working session where a company’s marketing, sales and technical leaders decide where artificial intelligence will create measurable revenue impact, and in what order to build it. A Gabriel Sales workshop runs one, two or three days, requires a completed maturity benchmark and Salesforce data readiness audit beforehand, and produces a ranked use-case list, a remediation sequence and a phased roadmap with named owners.

Why do we have to be benchmarked and audited first?

Because a workshop without evidence is a strategy offsite. The benchmark gives the roadmap its order of operations, and the audit turns “can we do this?” into a scored answer instead of an argument. It also protects your investment: we would rather tell you your data needs six weeks of remediation than discover it on Day 2 with six executives in the room.

What if we have not done either of them?

Start with the free Technology Health Check & Maturity Benchmark. If a workshop still looks right afterward, the readiness audit runs as pre-work in the three to four weeks beforehand and its findings become your Day 1 starting point. If the Health Check shows you need remediation more than a strategy session, we will tell you that.

What if we were audited by someone else?

Bring it. If the assessment is current and covers what our sessions need, field completeness against AI thresholds , sync and duplicate integrity, and governance we will work from that document after a short validation pass.

Do we have to hire the fractional executive afterward?

No. The workshop is a complete deliverable, and plenty of teams take the roadmap and run it themselves. If you do want us to own execution we will scope the fractional executives role.

Who needs to be in the room?

Marketing and sales leadership for the value sessions, and whoever owns your Salesforce org, your data and your integrations for the sequencing session. The two- and three-day formats deliberately separate those groups for part of the time so the technical read on feasibility is honest, then bring them back together.

How much does an AI strategy workshop cost?

Workshops are fixed-fee and scoped by format one, two or three days with the price confirmed during scoping.  Travel and expenses are quoted separately at cost.

What makes this different from a generic AI strategy workshop?

Every use case is sequenced against a completed audit of your own data, including Salesforce’s published minimums for Einstein features and/or are own thresholds for Claude, so you leave knowing what is possible now, what is possible after remediation, and what is not happening yet. Every recommendation is sequenced your stated goals on the Gabriel Sales Automation & Sales Enablement Maturity Matrix™, so you get an order of operations rather than a wish list.

Is it onsite or remote?

The two- and three-day formats are onsite. Being in the same room is most of why the alignment holds. The one-day format is available with some team members attending remotely.

What is a Fractional Automation, AI & Sales Enablement Executive?

A part-time senior leader who owns your post-lead revenue engine. This includes nurturing, lead scoring, sales enablement, the marketing-to-sales hand-off, lifecycle automation, and the AI and data readiness agenda underneath that anchors AI you can trust.  They direct a certified Salesforce build team to improve your stack and AI, for a fraction of the cost of a full-time hire.

How is this different from a fractional CMO?

A fractional CMO usually owns top-of-funnel strategy brand, demand generation and awareness.  This role owns what happens after the lead is generated, and comes with a certified Salesforce team to build the systems rather than simply advise on enhancements.

How is this different from a RevOps leader?

RevOps tends to own tooling and process across the whole funnel. This executive owns a specific outcome: converting demand you have already generated and keeping the customers you have already won, by strengthening nurturing, enablement, the hand-off and the lifecycle programs sequenced stage by stage on our maturity model.  They would support these areas for your RevOps leader.

Which platforms does this cover?

Salesforce Marketing Cloud Account Engagement (Pardot) for marketing automation, Sales Cloud sales-enablement features, Data Cloud for unified and governed customer data, Agentforce and/or Claude for AI agents that act inside your CRM, and the integrations that feed your nurturing and hand-off. If you are also weighing a Marketing Cloud Next migration, that decision is sequenced inside the same roadmap.

Everyone is offering us a free AI pilot. How do we tell which ones are worth the time?

By deciding what you are trying to prove before you accept one. A pilot is only worth running if it tests a use case you have already ranked, on data you have already scored, with a measure you have agreed in advance. Most free pilots fail that test. They demonstrate the vendor’s product rather than answer your question, and they quietly put company data into an environment nobody governs. The workshop produces the shortlist and the success measures first, which turns a pile of vendor offers into a decision you can make in an afternoon.

Should we use a general-purpose AI assistant instead of Salesforce AI?

Often both, for different jobs.  Salesforce’s AI (Einstein features inside Sales Cloud, and Agentforce agents that take action in your CRM) works on your governed CRM records and can write back to them, which is what you want for scoring, next-best-action and anything that has to touch a record. A general-purpose assistant is usually better for drafting, research, analysis and summarizing work that happens beside the CRM rather than inside it. The wrong answer is picking one on principle. We map each ranked use case to whichever is genuinely the better tool for it, and flag which ones your data volumes qualify for today.

We are spending on AI and cannot show the board what it bought. Can the workshop fix that?

That is usually a measurement problem created upstream, not a reporting problem. 31% of chief sales officers name difficulty proving the ROI of AI-driven tools as a top challenge for meeting their 2026 objectives. This is largely because nobody constructed the workflow to capture the value before the tool was switched on. Every use case that leaves our sessions has a way to measure it. We start with a baseline so the reporting exists before the spend does.

Can AI help with the customers we already have, not just new pipeline?

Yes, and it is usually the fastest return on the list. An entire track of every workshop explores post-close lifecycle onboarding and adoption nurturing, health and churn signals, renewal risk, upsell and cross-sell triggers, advocacy programs. Many marketing teams have not gotten this deep into the funnel.