Most vendor outreach fails before it's even opened. And most demos lose the deal before the second slide.

In this episode of The Human Side of MarTech, Sean Simon sits down with Chris Seahorn, Co-founder of Boundless Digital — a fractional CMO agency he started two years ago with a longtime colleague after 25+ years in digital marketing at companies like eBags, MapQuest, Naked Wines, and others.

Chris evaluates MarTech stacks across multiple clients simultaneously. He has an unusual vantage point: he sees what vendors do well, what kills deals, and what separates implementations that stick from ones that quietly die at renewal time.

In this conversation:

→ The StoryBrand framework: why "your customer is the hero" changes everything about how you sell

→ What makes Chris immediately delete a cold email (and what gets a meeting)

→ The "kitchen sink demo" problem — and how to fix it before you walk in the room

→ How a fractional CMO evaluates a client's tech stack from day one

→ Why conversion rate optimization is always the first quick win (and how 5% improvements stack to 25–30% total lift)

→ The most common checkout conversion killers: coupon confusion, account creation walls, and traffic mismatches

→ Why SaaS implementations fail — and it's almost never the product

→ AI customer service agents: why they went from "worse than useless" to genuinely impressive

→ The self-checkout analogy and what it tells us about AI adoption timelines

→ What Chris would tell his 1999 self: "Progress over perfection — trust your gut, but come with the receipts"

0:00 — Introduction: Chris Seahorn and Boundless Digital

1:30 — Chris's 25-year journey: eBags, MapQuest, Naked Wines, startups

3:30 — Why Chris left the CMO seat to go fractional

5:30 — What signals to Chris that a vendor actually understands his world

8:00 — The StoryBrand framework: hero, guide, problem, plan

11:00 — The "creep factor" — when vendor research goes too far

13:30 — Getting from inbox to meeting: breaking through the clutter

16:00 — What makes a good vs. bad vendor demo

19:30 — The kitchen sink problem: analysis paralysis in presentations

22:00 — Why use cases and follow-ups close more than the deck does

24:30 — How a fractional CMO walks into a new client

27:00 — The first assessment: looking at data before charging anything

30:00 — Evaluating a tech stack: measurement first, then fundamentals

33:00 — Email/SMS, CRO, and A/B testing as the foundation

36:00 — Conversion rate: the tide that lifts all ships

39:30 — Why 5% improvements on key pages beat swinging for 50%

42:00 — The most common conversion killers (coupon confusion, account walls)

45:30 — Seasonal behavior: why November cart abandonment is actually a good sign

48:00 — The tire store checkout story — friction that kills conversions

51:00 — Are consumers actually changing their behavior with AI?

54:00 — AI recommendation engines and what winning e-commerce brands do

57:00 — AI customer service agents: from worse-than-useless to genuinely impressive

60:00 — The self-checkout analogy and AI adoption timelines

63:00 — Why SaaS implementations fail: no champion, no success definition

66:00 — Chris's advice to vendors: step out of your own shoes

68:00 — The case for trials and reduced-rate pilots

70:00 — Advice to his early-career self: progress over perfection