Ever wonder why your carefully crafted outreach messages sometimes fall flat? The secret sauce to truly engaging prospects lies in personalized, context-aware messaging—messages that show you get their unique challenges and opportunities.
In this playbook, we’ll show you how Derrick App’s askOpenAI feature lets you instantly generate highly personalized content directly inside Google Sheets by leveraging the power of OpenAI’s language models. Say goodbye to manual copy-pasting or juggling multiple tools — automate your messaging at scale with AI-crafted precision.
Derrick App Features Used in This Playbook:
- askOpenAI: Generate AI responses dynamically based on prompts in your sheet
- Lead & Company Import: Easily bring your prospect lists into Google Sheets
- Data Enrichment: Add rich context to your contacts for smarter prompts
Use Cases Detailed in This Article:
- AI-Generated Personalized LinkedIn Icebreakers
- Automated Audience Segmentation
- Intelligent Lead Scoring Based on Pain Points
1. AI-Generated Personalized LinkedIn Icebreakers
Perfect for: Sales teams seeking to break the ice with warm, relevant messages that don’t feel robotic or generic.
How many times have you struggled to write unique LinkedIn openers that actually spark conversations? askOpenAI lets you automate this process by feeding contact details into AI-crafted prompts — producing natural, insightful icebreakers tailored to each prospect.
How to use it:
- Import your lead data into Google Sheets
- Write a prompt template in a column, combining static instructions with dynamic contact info (e.g., name, title, company)
- Use Derrick’s askOpenAI feature to process each row’s prompt and return a custom icebreaker
- Copy and paste or automate outreach directly from your sheet
Example prompt:="You are a B2B sales expert writing short, natural LinkedIn icebreakers. Based on this contact's info: First Name: "&A2&", Title: "&D2&", Company: "&E2&". Write a friendly and relevant opener."
2. Automated Audience Segmentation
Perfect for: Marketing teams needing to categorize large contact lists quickly and accurately.
Manually segmenting leads can be tedious and error-prone. With askOpenAI, feed the contact’s profile and company info into an AI prompt that outputs a precise audience cluster or segment — speeding up list building and campaign targeting.
How to use it:
- Prepare your contacts’ professional details in your sheet
- Design a prompt that instructs the AI to assign a segment based on defined criteria
- Run askOpenAI to generate segment labels for each contact
- Use results to tailor your marketing campaigns and messaging
Example prompt:="Assign this contact to one of these segments: Corporate Leaders, Tech Innovators, SMB Owners, Emerging Talent. Contact info: "&A2&", "&B2&", "&D2&", "&E2
3. Intelligent Lead Scoring Based on Pain Points
Perfect for: Sales ops and growth marketers who want to prioritize leads most likely to convert based on their marketing or acquisition pain.
Lead scoring can be complex, especially when relying on subjective data. askOpenAI lets you automate scoring by analyzing contact info and outputting a numeric score that reflects their potential need for your solution.
How to use it:
- Gather relevant contact details and job descriptions
- Write a prompt asking the AI to score the lead from 1 (low need) to 5 (high need) based on pain indicators
- Process the list with askOpenAI and prioritize outreach accordingly
Example prompt:="Score this lead from 1 to 5 on customer acquisition pain based on: Title: "&D2&", Company: "&E2&", Description: "&G2
Pro Tips
- Always test and tweak your prompts for clarity and specificity — better prompts = better AI responses
- Use askOpenAI in combination with other Derrick features for enriched, smarter outreach workflows
- Remember the 5,000 character limit per prompt — keep prompts concise but informative
- Mix static instructions with dynamic data pulled from your sheet columns for personalized results
Troubleshooting
- If responses seem generic, try adding more context or instructions to your prompt
- Prompt formatting matters — ensure your concatenated strings in Sheets are error-free
- Large datasets may require patience; process in batches if needed
- Make sure you have an active internet connection and valid OpenAI API access through Derrick
Ready to unlock AI-powered personalization at scale?
Try Derrick’s askOpenAI feature today — automate your messaging, segmentation, and lead scoring, all from the comfort of your Google Sheets. Say goodbye to manual work and hello to smarter outreach!
Jonathan Maurin
