Brochures/One-pagers:
- Initial interest → Overview brochure
- Specific feature inquiry → Feature sheet
- Executive audience → Executive summary

Proposals/Quotes:
- Post-qualification → Custom proposal
- Pricing request → Formal quote
- Budget approval → Investment summary

Technical Docs:
- Integration questions → API documentation
- Security concerns → Security whitepaper
- Implementation → Setup guides

Videos:
- Product overview (2-3 min demo)
- Feature deep-dives
- Customer testimonials
- How-to tutorials
- CEO/founder message

Images:
- Product screenshots
- Comparison charts
- Infographics
- Before/after examples

Interactive:
- ROI calculators
- Product configurators
- Assessment tools

Trigger: Question about specific feature

Prospect: "Does it integrate with Salesforce?"

Bot: "Yes! We have a native Salesforce integration.
Here's a quick video showing how it works: [link]

Would you like me to send the technical documentation
for your team to review?"

Intent: Comparing options

"I'm trying to figure out which solution is right for us"

Bot: "I have a comparison guide that might help. It shows
how we stack up on the features that matter most.
[Comparison PDF]

Any specific areas you want me to highlight?"

Awareness stage:
- Overview video
- High-level brochure
- Blog posts/thought leadership

Consideration stage:
- Feature comparison
- Case studies
- ROI calculator

Decision stage:
- Detailed proposal
- Implementation guide
- Contract/terms
- Customer references

Best for:
- PDFs and documents
- Long-form content
- Multiple attachments
- Formal proposals

"I've attached our proposal and implementation timeline.
Let me know if you'd like to walk through it together."

Best for:
- Short videos (<2 min)
- Single links
- Quick references
- Mobile-friendly content

"Here's a 90-second video showing exactly how that works: [link]"

Avoid:
- Large file attachments
- Multiple links
- Complex documents

Send content when:
✓ They asked for it
✓ It directly answers their question
✓ Natural pause in conversation
✓ Moving to next stage

Don't send:
✗ Unsolicited dumps of materials
✗ In the middle of active exchange
✗ Before understanding their needs
✗ When they're clearly on mobile

Customize based on:
- Industry (industry-specific case study)
- Company size (SMB vs Enterprise pricing)
- Role (technical vs executive view)
- Use case (their specific application)
- Stage (awareness vs decision content)

"Here's a proposal customized for [Company Name].
I've included:
- Pricing for your team of [number]
- The [Industry] case study you asked about
- Implementation timeline based on your Q2 goal"

Based on similar prospects:

"Prospects in [industry] often find these helpful:
1. [Industry] Case Study
2. ROI Calculator
3. Integration Guide

Want me to send any of these?"

content_library/
├── brochures/
│   ├── product-overview.pdf
│   ├── enterprise-overview.pdf
│   └── industry/
│       ├── healthcare.pdf
│       ├── fintech.pdf
│       └── retail.pdf
├── videos/
│   ├── demo-overview.mp4
│   ├── features/
│   │   ├── reporting.mp4
│   │   └── integrations.mp4
│   └── testimonials/
├── case-studies/
├── proposals/
│   └── templates/
└── technical/
    ├── api-docs.pdf
    └── security-whitepaper.pdf

def select_content(context):
    # Based on conversation context
    if context.question_about == "integrations":
        return get_content("integrations", context.specific_tool)

    if context.stage == "decision" and context.role == "executive":
        return get_content("executive-summary", context.industry)

    if context.objection == "security":
        return get_content("security-whitepaper")

    # Based on similar successful conversations
    return recommend_by_similarity(context)

Track:
- Content sent (what, when, to whom)
- Delivery confirmation
- Open/view events
- Time spent viewing
- Downloads
- Shares/forwards

Use signals:
- Viewed proposal → Follow up on it
- Watched full video → Higher intent
- Didn't open → Resend or call attention

Don't just drop links. Frame the content:

"Before I send this over—this is a 3-minute video showing
[specific thing]. It'll give you a better picture of
[what they asked about]. Want me to send it?"

Why:
- Sets expectations
- Gets permission
- Increases likelihood they'll view it

After sending:

Immediate:
"Just sent that over. Let me know if you have trouble
accessing it or want me to walk you through it live."

Follow-up (if no response):
"Did you get a chance to check out the [content]?
Happy to highlight the most relevant parts if helpful."

Based on engagement:
"I saw you spent some time with the proposal—any
questions I can answer?"

"I can't open the attachment"

Options:
1. Resend with different format
2. Share via different channel
3. Provide web-hosted link
4. Walk through live on call

"No problem! Here's a web link instead: [link]
Can you try that? If still an issue, I can walk you
through it on a quick call."

"I have several resources that might help:
- Product demo video (3 min)
- Feature comparison guide
- Customer case study

Which would be most useful right now?"

Early stage:
Send one thing, gauge interest

Late stage:
Bundle related materials
"Here's your proposal package:
- Pricing proposal
- Implementation timeline
- Security documentation
- Customer references"

Email: Can include multiple attachments
SMS: One link at a time
Chat: Mix of inline and links

Track content age:
- Last updated date
- Review schedule
- Deprecation flags

Alert when:
- Content over 6 months old
- Pricing outdated
- Statistics stale
- Screenshots don't match product

By content piece:
- Send frequency
- Open/view rate
- Time spent
- Correlation with advancement
- Correlation with close rate

Optimize:
- Promote high-performing content
- Update or retire underperforming
- A/B test variations