AI Career Tools: ChatGPT, VMock, and more

Blog Contributors: Heather Holland, Phoenix Vicari, Gayle Grader 

ChatGPT and other AI tools are making headlines with their potential to speed up and improve job search communication – including resumes, cover letters, career summaries and profiles, identifying skills, anticipating interview questions and other forms of job search communication and strategy. 

Do these tools really deliver? In short, yes: AI tools can be useful in your job search, especially if you approach them as resources for generating ideas and options, and take care to refine the results as well as protect your personal privacy. Read on to learn how to use these tools to your advantage. 

Philip Gerity, EMBA ’23 

We recently connected with MIT Sloan EMBA ’23 Philip Gerity about his experience using AI tools to refine his value proposition/elevator pitch. Philip used ChatGPT to generate a rough draft of his elevator pitch, which he refined. He then used Loom to practice his pitch to perfection. 

The most useful part about using AI technology as part of his career communication strategy: “It’s a way to get started quickly. It’s a way to get that rough draft out there, and it may not be perfect, but it’s a really good starting point that you can build from. I used ChatGPT to get going with initial ideas, have a conversation with the AI that generates some useful starting points; and then I take it from there, edit it down, and refine it to capture my insights and my voice.”

When used thoughtfully and strategically, AI tools can be a useful addition to your career communication toolkit: 

1) Use it to get started and to generate ideas. AI technology excels at gathering input information and generating different options quickly – helping you to pivot from long versions to short versions of your career pitch, and to explore different tones or approaches. It can also be used to gain insights and language about your industry and transferable skills. For example, one could enter the prompt “I worked as a Product Engineer for 4 years at a growing B2B technology company, what are the different skills I developed in that role?” 

2) Refine your draft, using your own insights, expertise, and voice. Remember that you have arrived at a unique and specific place in your career. While typical AI tools can create boilerplate responses for typical career paths, AI tools falter the more you deviate from entry-level or easily-categorized roles. With most AI tools, you bring the insight and expertise. Exception: The CDO has invested in two AI tools, VMock and Big Interview, that have been specifically trained on top business school career paths and communications. We encourage you to leverage these tools for 24/7 support and practice. Read more about these tools below. 

3) Consider your privacy. One reason to approach public AI tools with caution: they work by leveraging the information you and other share with it. ChatGPT ‘learns’ from the information input by developers and users, so if you share information with it, expect it to store this information. We encourage you to read OpenAI’s privacy policies and be cautious about sharing any personal or sensitive information with it. 


VMock for Master’s Level Executive Resumes 

AI tools are only as good as the information they are fed, which makes them problematic for writing targeted resumes for unique or sophisticated job roles. Recognizing the power of AI to offer good advice on master’s-level resumes if trained on relevant examples, the CDO jumped in as early adopters of this AI technology through a partnership with VMock.

VMock Smart Resume is an AI-powered resume feedback tool designed specifically for business students, created through analysis of thousands of resumes from top business school graduates. The tool can provide feedback on how well the resume demonstrates key competencies including communication, leadership, and teamwork skills, and taking initiative.

VMock Aspire is an AI-powered LinkedIn optimization application, allowing you to create a consistent narrative from your resume to your LinkedIn profile, to align your LinkedIn profile with your target career track.

Big Interview: Practice Your Pitch and Interview Skills 

An important element that Philip Gerity EMBA ’23 incorporated into his pitch was practice. While he used Loom for this, the CDO offers an AI tool that can help you practice your elevator pitch, including ‘walk me through your resume’ and ‘tell me about yourself’, and your interview skills: Big Interview. 

For interview practice, Big Interview offers two paths for practice: The Fast Track is intended for users who have an interview coming up in the next few days or do not have a lot of time to prepare. It takes about an hour and a half to complete. The Mastery Track covers more in-depth content for more competitive/difficult interviews. When you click on the Practice Interviews area, you will see six interview categories to choose from. We recommend that you start with General Practice as these practice interviews will cover 80% of questions that come up in actual interviews.


We are excited about the ways AI tools can help us speed up and re-imagine our job search communications, but sometimes human insights are what you need! Contact the CDO for support with your job search. Visit your program’s page on Your CDO to learn how to connect with Career Advisors and Coaches who can help you navigate career resources and career decisions. 

Not sure where to start? Email us at 

By MIT Sloan CDO