Lincoln Park Chamber of Commerce
Marketing Mastermind
Wednesday, April 22  ·  12:00 – 1:15 PM CT

Do You Actually Need AI?
A Practical Guide for Everyday Business

No hype. No tool tours. Just an honest conversation.

WS
Will Seide
Founder & Managing Partner · Pivotal Pathways Consulting
AI Innovation
Your Host

Meet Will Seide

Will Seide
15+
Years Enterprise Software & AI
IBM
Early Watson Era
Big Data
Led AI/ML Proof-of-Concepts
ERP
~10 Yrs Midsize Biz Systems
Started at IBM: predictive analytics & Watson era
Senior leadership at a big data AI startup
Nearly a decade modernizing ERP systems
Finance · Operations · Sales · Supply Chain
Active Clients: Insurance, Construction, Distribution, Professional Services & more
Today's Session

Here's What You'll Walk Away With

01
Clarity on where AI actually fits, and where it doesn't
Cut through the buzzwords and get a real picture of what AI can do for a business like yours.
02
Real examples of connected marketing systems
Not theoretical. We'll show real workflows built for businesses just like yours.
03
A practical framework to evaluate AI for your business
Walk away with a decision model, not a sales pitch.
04
A starting point, not a 6-month project
One workflow. One win. Build from there.
Today's Roadmap

What We'll Cover

Welcome, Intro & Framing VideoContext
From Broad Communication to Smarter Engagement, What Actually ChangedThe Shift
Where Marketing Time Goes + Data Silos, The Structural ProblemThe Problem
What Changes When Marketing Is a System, Before & AfterThe Solution
How The System Decides, Then Live Hyper-Personalization DemoDemo
3 Use Cases: Newsletter, Outreach at Scale & Intelligent Lead PipelineUse Cases
Full Intelligence Loop, Knowledge Base & Brand VoiceInfrastructure
People > Process > Tech, Maturity Model & GuardrailsFramework
How Pivotal Pathways Works + Next StepsHow We Help
Open Q&A & pivotalpathwaysconsulting.comClose
Before We Start

Four Ways to Get the Most Out of Today

Focus
Focus
Close the tabs. This is time that could reshape how you work every day.
Participate
Participate
Use the chat. Get specific about your business. No bad questions.
Take Notes
Take Notes
You don't need to do everything. One good idea is enough to start.
Think Outside the Box
Think Outside the Box
Stay curious a little longer. The businesses winning with AI did not find a perfect fit, they made one.
Setting the Stage

Before We Build Systems
Let's Start With This.

The Shift
From Broad Communication
to Smarter Engagement
How the delivery model has changed, and why demographics, voice, and channel now determine what actually lands
Traditional Outreach
Marketing in the AI Era
Audience
Broad assumptions, one message for all
Age, business stage, and engagement history are ignored. Same email goes to a 28-year-old founder and a 62-year-old established owner.
Audience
Segmented by demographics, behavior, and need
Age, industry, engagement history, and interests shape who gets what message and when. Different generations respond to different formats and timing.
Voice of Customer
Occasional and fragmented
Lives in event conversations, scattered email replies, and annual surveys. Hard to act on and always delayed.
Voice of Customer
Continuous and multi-channel
Email clicks, event behavior, website actions, CRM notes, reviews, and direct feedback all become usable signals, in real time.
Delivery
Static channels, pushed outward
Newsletters, printed handouts, flyers, general social posts. Value exists but members have to work to find it.
Delivery
Easier to access, easier to act on
Short-form email, mobile touchpoints, QR access, personalized recommendations, and digital hubs reduce friction and meet people where they are.
The Shift, Continued
Behavior-Driven Follow-Up
and Measurement That Moves
The last mile: what happens after the message goes out determines whether communication becomes engagement
Traditional Outreach
Marketing in the AI Era
Follow-Up
Manual, generic, and often too late
Whoever has time makes the call. Members are informed but not guided toward a next step that actually fits where they are.
Follow-Up
Timely, relevant, and behavior-triggered
Members get the next best action based on what they actually did, not a generic blast sent to everyone three days later.
Measurement
Reporting looks backward
Open rates and attendance counts tell you what happened after the moment passed. Decisions are made on data that is 30 days old.
Measurement
Feedback improves the system in real time
Content, outreach, and event strategy adjust based on what people actually engage with. The system gets smarter with every interaction.
"This is not about replacing relationships. It is about making the value you already provide easier to access, easier to act on, and easier to scale."
The Pivotal Pathways Frame
The Real Problem

Where Marketing Time Actually Goes

These are not people problems. They are system problems.

Lead follow-up
Manually tracking who responded, who ghosted, who needs another touch.
Hot leads go cold while you are busy with cold ones
Content creation
Writing emails, social posts, and campaign copy from scratch, every single time.
Brand goes quiet during busy periods when marketing matters most
Social scheduling
Posting manually platform by platform with no system for repurposing high-performing content.
Inconsistent presence erodes trust with your audience over time
Campaign reporting
Pulling data from 3 different platforms, building a spreadsheet, already a month out of date.
Budget and strategy decisions made on stale information
List & CRM hygiene
Removing bounces, tagging contacts, updating segments, all done manually and usually behind.
Campaigns send to the wrong people and damage deliverability
The opportunity
Every one of these is a system problem, not a people problem. And every one has an automation solution that runs without a human in the loop.
Give your team their time back.
The Structural Problem

Data Silos and the Marketing Disconnect

View:
Click any department to see its data
Each department captures valuable signals every day. Almost none of it reaches marketing in time to matter.
Step 1
Data Signals
Captured in each dept
→
Step 2
Automation Routes
Moves data to the center
→
Step 3
AI Interprets
Scores, classifies, decides
→
Output
Marketing
The high-value layer
Data provides the signals. Automation moves them. AI interprets and acts. Marketing becomes the intelligent output.
The Connected Difference

What Changes When Your Marketing Is a System

Today: Disconnected
Leads sit in a spreadsheet
Manually reviewed when someone has time, often days later
Generic messaging for everyone
Same email, same CTA, regardless of industry, role, or intent
Inconsistent follow-up
Depends on who is available, not on how important the lead is
Backward-looking reporting
Monthly summaries of what happened 30 days ago
Campaigns restart from scratch
No institutional memory, same work every cycle
Wasted motion. Missed timing. Slower growth.
→
After: Connected System
Leads routed instantly
High-intent signals trigger CRM updates and sales alerts in real time
Adaptive messaging by persona
The right headline, proof point, and CTA, based on who someone is
Behavior-based follow-up
Follow-up fires based on signals, pricing page visits, form fills, repeat engagement
Real-time reporting
Dashboards show what is working now, not what worked last month
Marketing gets smarter each cycle
Each campaign informs the next, the system learns and improves over time
Better leads. Faster follow-up. Smarter decisions.
Marketing is no longer just campaigns, it is a system. And systems improve over time.
The Foundation

Before We Look at the Systems

"You do not rise to the level of your goals. You fall to the level of your systems."
James Clear, Atomic Habits
Without systems
Good intentions. Inconsistent execution. Data sitting unused.
→
With systems
Consistent execution. Data flows. Marketing outputs at scale.
Most businesses do not have an AI problem. They have a systems problem. What follows is what a connected system looks like with marketing as the high-value output.
Under The Hood

How The System Decides In <500ms

01
🌐
Visitor Arrives
Page loads. System starts reading, before a single click.
URL & UTM params
Referrer source
Session history
→
02
📡
Signals Collected
Real-time data from 4 sources, combined into one profile.
IP firmographic
Behavioral events
CRM record match
→
03
🤖
AI Classifies
Weighted rules score each signal. Confidence threshold determines the call.
Score: HVAC 75%
Score: Retail 12%
Score: Ops 8%
→
04
✨
Experience Adapts
Headline, proof points, case study, CTA, all switch. Automatically.
No page reload
No human trigger
<500ms total
This is not A/B testing, it's individual-level response.  Let me show you live.
System 3: Interactive Timeline

The Full Intelligence Loop: Marketing as the Output

💬
Sales Alerts
Hot prospects flagged in real time
🎯
Campaign Optimization
Every cycle learns and improves
🔁
Re-engagement
Lapsed contacts re-entered automatically
📊
Live Dashboards
Real-time performance at a glance
The Brand Intelligence Layer

Knowledge Base, Brand Voice and Brand Kit

What goes into the knowledge base
V
Brand voice guide
Tone, style, vocabulary, phrases to use and avoid. Every output sounds like you.
K
Brand kit
Colors, fonts, imagery standards, logo rules. AI-generated content stays on-brand visually.
D
Business and campaign data
Services, personas, past campaign performance, customer segments, and win/loss notes.
I
Instructions, how the AI should behave
Tone: conversational, direct, avoid jargon
Emphasize: outcomes and ROI, not features
Avoid: hype words ("revolutionary", "disruptive")
Format: question headlines, emails 200 words max
Review: all customer-facing outputs approved first
Supported tools & what your team can do
🤖 ChatGPT
🟣 Claude
📓 Notion AI
Your Brand
Your AI Knowledge Base · Brand-Trained
What subject line angle would work best for local professional services leads?
Question-format subjects get 3.2x better opens in your professional services segments. Example: "Is your follow-up process costing you deals?"
Write a follow-up email for a construction prospect who clicked but didn't register.
Done. In your brand voice, under 180 words, outcome-focused hook. Ready for review before sending.
What are the top objections showing up in our outreach?
Based on your last 90 days: pricing clarity (34%), timeline concerns (28%), and "we already have a vendor" (22%). Drafting rebuttal angles now...
Create 3 LinkedIn post ideas based on our webinar theme.
Drafting now with your formatting rules: hook in line 1, no jargon, outcomes-first framing...
No data scientist. No agency. Anyone on your team can use it in plain language.
The Framework

People → Process → Technology

Skip People or Process and jump to Technology, the project fails. Follow all three, you build something that lasts.

Layer 1: Foundation
People
Who owns it · Who changes · Who maintains it
Layer 2: Structure
Process
Map it · Identify waste · Redesign for clarity
Layer 3: Accelerator
Technology
Now choose tools · Connect systems · Add AI decision points
Success
Your Path Forward

Where AI Actually Fits: Three Levels of Maturity

1
Level 1
Tasks: Disconnected
Using AI tools one at a time, for individual tasks. No connection between them.
ChatGPT for drafting one email at a time
Canva AI for individual social posts
Copy.ai for occasional content
Manual steps between every tool
Results: time savings on individual tasks, no compounding value
2
Level 2
Workflows: Momentum
AI and automation connected in workflows. Repeatable, reliable, reduces manual work.
Form fill → CRM update → email sent
Lead scored → sales alert triggered
Content scheduled → posted across platforms
Reporting automated on a cadence
Results: consistent execution, team gets time back
3
Level 3
Systems: Results Scale
All workflows connected. Data feeds intelligence. Marketing improves automatically over time.
Ops signals trigger marketing campaigns
AI personalizes by persona in real time
Every cycle learns from the last
Marketing as the high-value output layer
Results: better leads · faster follow-up · smarter decisions · compounding ROI
You do not have to start at Level 3. You start where you are, and build. The goal is a clear path to connected systems.
Guardrails

Guardrails: Deploying AI Responsibly

1. Where to start
Start internal before external. Automate what your team sees before you automate what your customers see. Get confident in how the system behaves before it represents your brand.
2. Customer-facing AI
The bar is higher. A wrong answer, a tone-deaf message, a personalization that misses, these are not errors. They are brand moments your customer remembers.
3. Behavior change
Automation changes how people work. If your team does not understand why the system works the way it does, they will work around it. This is a change management project.
4. Human in the loop
AI will make mistakes. The question is whether you have a human checkpoint at the right moment to catch them before they reach a customer. Design that from day one.
The businesses that earn long-term trust with AI are not the fastest movers, they are the most intentional ones.
One Step After Today

You Don't Need a 6-Month Plan. You Need One Step.

1
🔍
Identify one task
Find one thing your team does manually every week that follows a repeatable pattern. It doesn't matter how small. That is your starting point.
Lead follow-up? Content publishing? Reporting?
Ask: "What do we do the same way every time, that a system could do for us?"
2
🔗
Connect two tools
Look at the tools you already have. Find one place where a person is manually moving information from one system to another. Connect them.
Form → CRM Email → Spreadsheet CRM → Alert
Ask: "Where are we copy-pasting, exporting, or manually updating something?"
3
⚙
Build one workflow
Use a simple automation tool, Zapier, Make, or n8n, to connect those two steps. Run it for 30 days. Measure what changed.
Time saved? Errors reduced? Speed improved?
Outcome: You now have proof of concept, and momentum to build the next one.
Every great connected marketing system started with one workflow. Start there.
www.pivotalpathwaysconsulting.com
How We Can Help
Pivotal Pathways Consulting
Education first. Engagement second: only when it makes sense.
AI Strategy & Data
AI & Data Strategy
Strategy, roadmaps, and data systems that drive decisions
Workflow Automation
Workflow Automation
Eliminate manual steps and build systems that scale
Data Analytics
Data Analytics & Reporting
Turn raw data into decisions that drive performance
📱
Custom Business Applications
Purpose-built apps and tools designed around your operation
👥
Team Training & Enablement
Practical skills your team can apply the next day
How We Work
Project · Retainer · Assessment
Proof-of-concept first, always
Small pilots → proven ROI → scale
Industry agnostic · Business-size neutral
🌱
"The best time to plant a tree was 20 years ago. The next best time is today."
The Goal for Today

By Now, You Should Be Thinking...

✓
"Marketing is no longer just campaigns, it is a system. And systems improve over time."
✓
"AI alone is not the advantage. Connected systems are."
✓
"Most businesses do not need more tools, they need their tools working together."
✓
"The goal is not more activity, it is better outcomes. Better leads, faster follow-up, smarter decisions."
Intelligent marketing engine, built on AI, Automation, and Analysis.
Team success
Pivotal Pathways team
Pivotal Pathways Consulting
Lincoln Park Chamber of Commerce
Lincoln Park Chamber of Commerce · April 22, 2026

Thank You

Open Q & A

Pivotal Pathways Consulting · Chicago, IL
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