Building an Automated Email System Using OpenAI

Published: June 19, 2024
Last Modified: June 30, 2024

NOTE: This article contains referral links to various services I used in building my automated email system. Please consider using my links to explore these tools and support my ongoing projects.

Embarking on the journey of building an automated email system with OpenAI AI has been a fascinating and rewarding experience. Through various challenges and iterations, I’ve gained valuable insights into integrating multiple APIs, managing data, and automating processes. Remarkably, all of this was accomplished in less than seven days, thanks to the incredible assistance of ChatGPT AI. Given that I am not a software engineer, this would have been nearly impossible for me to achieve in such a short period without the help of Generative AI. My background as a Product Manager played a crucial role in planning and executing this project effectively.

The Beginning: Concept and Initial Setup

The idea started with a simple goal: automate the process of selecting the most engaging news article, crafting a personalized email from my dog, Pasquale’s perspective, and sending it to a list of subscribers. The initial setup involved configuring various modules and APIs:

  • PSReadLine: To enhance the command-line experience.
  • Airtable API: For managing and retrieving subscriber information.
  • OpenAI API: To generate content and decide which news article to feature.
  • SMTP2GO: For sending out the emails.
  • To curate the RSS feed used to produce articles for ChatGPT.

Evolution of the Email Components

Creating a consistent and professional email format was crucial. I developed a standard email structure that included a signature with links and an image, along with a message template to introduce the content. This helped maintain a cohesive appearance for each email, ensuring that every message looked polished and well-branded.

Fetching and Cleaning News Data

Fetching the latest news articles from an RSS feed curated using was straightforward, but processing the data presented its challenges. The JSON data included various articles, each with an ID, title, and content. Initially, I faced issues with special characters causing errors during processing. To overcome this, I implemented a cleaning function to remove unwanted characters and filter out problematic articles. This step was crucial in ensuring the data was ready for the next phases.

Selecting the Most Engaging Article

Using OpenAI’s GPT-3.5 AI to pick the most engaging article was one of the most exciting parts of the project. I crafted detailed prompts listing all articles with their IDs, titles, and content. The API would then select the most interesting one based on criteria like innovation, controversy, and impact. Extracting the chosen article’s ID from the API response was initially challenging, but refining the prompt and processing logic improved accuracy and reliability.

Crafting Personalized Emails

Once the top article was selected, the next step was crafting a personalized email. Using OpenAI AI again, I created prompts to generate email content from Pasquale’s perspective. The emails needed to be friendly, engaging, and provide key takeaways. Ensuring the response was correctly formatted for HTML email involved several iterations and adjustments to handle different types of content effectively.

Sending Emails

Retrieving the list of recipients from Airtable and sending the emails via SMTP was the final step. I had to ensure the recipient list was clean, removing duplicates and filtering based on test or live modes. Generating unique unsubscribe links for each recipient using the Softr API added an extra layer of personalization and compliance.

Overcoming Challenges and Improving Robustness

Throughout this journey, several challenges required creative solutions:

  • Data Cleaning: Implementing robust data cleaning to handle special characters and ensure smooth processing.
  • Error Handling: Adding detailed logging and graceful exits to manage errors during API requests or email sending.
  • Hard-coded Recipients: Initially, the script used a hard-coded recipients list. Switching to an Airtable database enhanced automation by dynamically fetching the list of recipients.
  • Testing Changes: Adding a test mode allowed me to test changes without sending emails to the entire list of recipients, making the development process safer and more controlled.
  • Purchasing a Domain: Acquiring the domain “” helped establish a brand identity, associating emails with a professional domain.
  • No-Code Integration: Connecting the Airtable database to the Softr no-code platform enabled new subscribers to sign up easily and automatically populate the database used by the application.
  • Duplicate Emails: Discovering and addressing instances of duplicate subscriber emails improved the accuracy of recipient lists by implementing a method to ensure unique emails.
  • Custom Domain in iCloud Mail: Configuring the new domain as a custom domain in iCloud Mail allowed replies to be managed effectively with minimal cost and setup.
  • Unsubscribe Functionality: Updating Softr to allow users to unsubscribe provided a user-friendly way to manage email preferences, enhancing compliance and user satisfaction.

Leveraging Product Management Skills

As a Product Manager, my experience in planning, executing, and managing projects played a crucial role in the successful implementation of this automated email system. Understanding user needs, defining clear goals, and iterating on feedback allowed me to adapt quickly and overcome obstacles. This project showcased the synergy between product management and Artificial Intelligence, demonstrating how AI can be leveraged to enhance productivity and deliver personalized user experiences.

Reflection and Future Directions

Building this automated email system has not only enhanced my technical skills but also demonstrated the potential of AI in transforming how we manage communications. The journey has been filled with learning, problem-solving, and continuous improvement, making it a truly rewarding project. Accomplishing all this in less than seven days, with ChatGPT as a partner, highlights the transformative power of Generative AI in simplifying complex tasks.

However, the journey doesn’t end here. OpenAI’s API will often timeout, which, according to OpenAI’s support, is unrelated to my prompts and may equate to growing pains. I am actively adjusting my processes to avoid erroneous instances like this. Additionally, I am considering adding user control over Pasquale’s topic of the day, allowing the content to be catered to each subscriber’s preferences.

Embracing the power of automation and AI has opened up new possibilities and streamlined the way I engage with my audience. The adventure of tinkering with AI continues, and I look forward to exploring even more innovative ways to leverage technology.

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