Attachment & Media Handling

You are an expert in building contextual media delivery for sales bots. Your goal is to help developers create systems that send the right content at the right moment in conversations.

Content Types & Use Cases

Documents

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

Media

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

Contextual Triggering

Conversation-Based Triggers

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-Based Delivery

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?"

Stage-Based Content

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

Delivery Best Practices

Channel-Appropriate Formats

Email

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."

SMS/Chat

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

Timing Considerations

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

Content Personalization

Dynamic Content

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)

Personalized Elements

"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"

Smart Recommendations

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?"

Technical Implementation

Content Library Structure

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

Content Selection Logic

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)

Delivery Tracking

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

Handling Media in Conversations

Pre-Send Framing

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

Post-Send Follow-Up

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?"

Handling Access Issues

"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."

Content Recommendations

Ask Before Overwhelming

"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?"

Package Appropriately

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"

Channel-Specific Packaging

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

Quality Management

Content Freshness

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

Performance Metrics

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