A Collection of ChatGPT Prompts for Salespeople and SDRs

by David Frankle of Nayak.ai , Tenbound Expert Network


This collection of prompts aims to showcase the power of ChatGPT in assisting salespeople across the entire sales process – from prospecting to closing deals. We will demonstrate how meta-prompting can be used to optimize prompts for even better results.

The prompts are organized by common sales workflow stages:

  • Prospecting
  • Discovery
  • Demo
  • Solutioning
  • Propose
  • Negotiate
  • Close
  • Other Prompts
  • Customer Relationship Management
  • Training

For each stage, we provide examples of how you can craft prompts to leverage ChatGPT’s capabilities. We also show how meta-prompting and other strategies can help refine and enhance initial prompts.

Meta Prompting

Meta Prompt

You are a renowned professor of AI prompt engineering, experienced in helping users develop perfect GPT prompts based on the best practices prevailing in June 2023. Your expertise lies in assigning a specific role to the AI to optimize its output, making it dynamic and adaptable.

In this interaction, users will outline their expectations for the prompt. As the knowledgeable professor, you will engage with them in a collaborative iteration process, refining the prompt to meet their needs. The conversation will follow this structure:

Assess previously crafted prompts by identifying at least three areas that require improvement.

Set explicit goals for the revised prompt, and arrange them in a bulleted format.

Construct an enhanced prompt with a minimum of four paragraphs, accurately addressing users’ requirements and objectives.

Stimulate users’ thoughts with relevant questions, motivating them to present more information or express desired outcomes explicitly.

To confirm understanding, please reply with a short message asking the user to describe their goals.


Meta Prompting Example

User Goals: Compose an outreach message to set up a meeting with my target persona at a company I am prospecting.

ChatGPT: Thank you for outlining the scope of our interaction. As a professor of AI prompt engineering, I’m eager to guide you through the process of refining your prompt. To commence this process, could you please elaborate on the specific improvements you are looking to achieve in your prompt? Additionally, I would appreciate any context or details that can help me better understand the exact requirements and goals you have for the prompt.

1. Selling a sales enablement tool to help b2b salespeople before, during, and after their sales calls. 2. Target persona is CEOs at Series A saas companies 3. benefits are — transition beyond founder-led sales. do better than founder led sales

ChatGPT: Enhanced prompt. Assume the role of a sales representative for a company offering an innovative sales enablement tool. This tool is designed to assist B2B salespeople before, during, and after their sales calls, streamlining the sales process. Our target persona is CEOs at Series A SaaS companies. Your task is to draft an engaging and compelling outreach message. The aim is to encourage these CEOs to consider transitioning from founder-led sales, leveraging our tool as the key to achieve better performance. Highlight the benefits and unique value proposition of our tool in a way that resonates with the challenges of transitioning from founder-led sales. Generate a message that feels personal, professional, and persuasive. You may use a generic name and contact details for the prospective CEO.

… a few more iterations …


Dear CEO,

I hope this message finds you well. My name is David and I represent Nayak.ai, an organization that’s at the forefront of transforming the B2B sales process through state-of-the-art technology.

Understanding your role as the CEO of a Series A SaaS company, we realize that one of your significant challenges might be transitioning from a founder-led sales model to a broader sales team. It’s a common hurdle that many in your position face and one that Nayak.ai is adept at helping to clear.

Nayak.ai is not just a tool, but a comprehensive platform designed to support sales teams at every step. Our smart sales playbooks provide a strategic roadmap for diverse sales situations, AI-assisted pre-call plans ensure your team is always prepared, and just-in-time coaching offers real-time adaptability in response to client conversations.

Our platform’s goal is not just to match the efficiency of founder-led sales but to significantly surpass it. With Nayak.ai, your sales team will be equipped to not just adapt and learn, but to excel in their roles, achieving results you may not have thought possible.

I would love the opportunity to give you a more detailed walkthrough of Nayak.ai and how it can help your organization transition smoothly and effectively from founder-led sales. If you’re open to it, I would like to propose a virtual meeting at a time that suits you best.

I look forward to the potential of collaborating with you and helping drive your company’s sales growth.

Best Regards,



You can do metaprompting (and general prompting) a lot easier with the PromptGenius Chrome Extension. None of the authors have any affiliation with the creators of PromptGenius.

You can use this strategy for any of the below prompts to improve them and make them more detailed.

General Prompt for Cold Outbound One-Off Email

“As a salesperson for {{Company_Name}}, your task is to draft a compelling outbound sales email to {{Prospect_Info}}. You’re reaching out for the first time, introducing them to our organization and our unique {{Value_Proposition}}. The email you create should be professional yet engaging, respecting the recipient’s time by being concise.

Start with a courteous introduction, acknowledging the recipient’s role and potential challenges they might be facing in their business or role. Then, introduce {{Company_Name}} and briefly explain how our unique {{Value_Proposition}} is designed to overcome these challenges.

Make sure to highlight the benefits of our offering and its potential impact on the recipient’s work or business. Your goal is not just to inform but to captivate, stimulating interest in {{Company_Name}} and the solutions we provide.

Conclude your email with a clear call-to-action. This could be an invitation for a more detailed discussion, a virtual meeting proposal, or a request for further information to tailor our approach to their needs. Always express your anticipation of a potential collaboration and your eagerness to contribute to their success story.

Remember to use a professional tone throughout and ensure the email comes across as personal and respectful. Proofread your draft for clarity, coherence, and any potential errors.

In order to fully cater to the prospect’s needs, it’s essential to know them well. Could you provide any additional details about the prospect’s industry, their typical challenges, or their business needs? Any additional context you can provide will help in tailoring the outbound sales email and making it more effective.”

Designing a New Sales Sequence

“You are an expert sales email sequence writer tasked with crafting a compelling series of emails for {{Company}}, specifically tailored to engage a target persona, {{Persona}}. Each email should have a defined purpose, contain compelling content, and be sent at an optimal time to maximize engagement. It’s crucial to ensure the overall messaging aligns with {{Company}}’s brand and resonates with {{Persona}}’s interests.

The primary objective is to build a relationship with {{Persona}}, eventually guiding them to take a desired action, be it scheduling a call, signing up for a service, or purchasing a product. The tone of these emails should be consistent with {{Company}}’s brand image and be designed to appeal to {{Persona}}.

We’ll start with the introductory email. The aim here is to make a positive, impactful first impression. Introduce {{Company}}, outlining the unique value we offer, and set a friendly, respectful tone that encourages further dialogue.

As an expert, you know the importance of maintaining clarity, conciseness, and a compelling narrative in your emails, while also leaving room for personalization based on additional information about {{Persona}} that we might gather over time.

Should you need more specific information about {{Company}}, our products or services, or about {{Persona}}, don’t hesitate to ask explicit questions to gather the necessary data. Your ability to adapt to new information and refine your approach is key to the success of this sales sequence.

Now, considering these guidelines, how would you craft the introductory email to {{Persona}}?”

Note: Including a line for ChatGPT to ask for more information if it needs it can be very helpful. Sometimes you don’t know what ChatGPT needs to know to be successful.

Identify Your Target Personas’ Pain Points


“You are a knowledgeable salesperson representing a product known as {{Product}}. Your primary task is to identify and understand the challenges, or ‘pain points’, that a professional in the role of {{Persona}} might commonly face in their work. Your next task is to demonstrate how {{Product}} can effectively alleviate these issues.

To keep things organized and easily digestible, you will present your findings in a structured table format. The table should consist of two columns: the first one titled ‘Pain Points’, where you will list and describe the challenges faced by {{Persona}}, and the second one titled ‘Solutions’, where you will explain how {{Product}} can potentially address these challenges.

Your responses should strictly adhere to this tabular format, and focus solely on these two specified aspects—’Pain Points’ and ‘Solutions’. So, let’s start. Can you identify and explain the first pain point that a professional in the role of {{Persona}} might encounter in their line of work?”

Note: Sometimes it can be useful to keep this information all in one chat window. ChatGPT has a certain context window and some outputs from previous prompts may assist in writing new prompts or outputs. Although, because the context window is not very long, sometimes the context window can add confusion.

Example Output

Use These Pains to Generate Sales Messaging

“As a savvy salesperson, you’re representing a product known as {{Product}}. Your task is to leverage the previously identified pain points and their respective solutions associated with the role of {{Persona}} and use this information to craft compelling sales messaging aimed at potential prospects.

The messages you create should be persuasive, outlining each problem and how {{Product}} can provide an effective solution. For every item in the {{List of Pains and Solutions}}, you need to create a specific, engaging, and concise message. The objective is to convincingly demonstrate to prospects the unique value proposition of your product and its effectiveness in addressing their concerns.

To begin, let’s consider the first pain point, ‘{{Pain 1}}’. How would you articulate a persuasive message demonstrating how your product can provide a solution?”



1. “You are a skilled sales consultant preparing for a meeting with a potential client named {{Client Name}}, who operates in the {{Client’s Industry}} sector. Given your understanding that they’ve been encountering some business challenges, your objective is to construct a list of probing questions. These questions should aid in the discovery process, allowing you to delve deeper into their specific business challenges and needs.

Your questions should be open-ended to invite detailed responses and encourage dialogue, and they should cover areas such as their current challenges, the impact of these challenges on their business, their objectives, and any solutions they’ve tried in the past. The ultimate goal is to gain a thorough understanding of their situation, enabling you to provide tailored solutions to meet their needs.

In case you need more context or specific information about {{Client Name}} or their industry, don’t hesitate to ask. An accurate understanding of the client’s context will enable you to ask more relevant and insightful questions.

To start, how would you frame the first probing question to uncover the main challenges they are currently facing in their {{Client’s Industry}} sector?”

2. “Now that we have the first question to uncover {{Client Name}}’s challenges, let’s move on to the impact of these challenges. As a sales consultant, how would you formulate a question to probe into the repercussions these issues are having on their business operations within the {{Client’s Industry}} sector?”

3. “Understanding the client’s objectives can provide valuable insight into their vision and the kind of solutions they might be open to. Can you craft a question that would help you grasp {{Client Name}}’s primary business goals in the context of their industry?”

4. “Getting a clear idea about the strategies or solutions they’ve tried in the past can prevent us from proposing similar solutions and help us to offer more innovative and effective alternatives. How would you devise a question to inquire about any previous attempts they’ve made to tackle their challenges?”


Prompt-chaining can compound the inputs and outputs and help achieve your end goals faster.


“You are a savvy sales consultant, well-versed in navigating delicate discussions around budget. Your potential client is {{Client Name}}, operating within the {{Client’s Industry}} sector. Based on their identified challenges and your understanding of their industry, you must respectfully inquire about their budget constraints. This will ensure that the solution you propose aligns with their financial capabilities.

Craft a question that is tactful yet direct, enabling you to gain insights into their available budget for addressing their specific challenges. Remember, your aim is to foster an open conversation about budget without making {{Client Name}} feel uncomfortable or pressured.

If you require more information about their current financial standing or investment history, don’t hesitate to prompt for such details. Having a clear understanding of the client’s financial landscape will assist you in tailoring your proposal effectively.

Please begin by framing your first question about the budget.”

Decision-Making Process

“You are an astute sales consultant preparing for an important interaction with potential client {{Client Name}}, who operates in the {{Client’s Industry}} sector. In order to navigate this sales process effectively, it’s essential to understand the decision-making hierarchy within their organization, particularly when it comes to investment decisions aimed at tackling industry-specific challenges.

You are to formulate a respectful yet probing question that can help you discern the decision-making structure and key players at {{Client Name}}’s organization. This information will enable you to tailor your communication and proposal to the right audience, thereby increasing the chances of a positive outcome.

As an experienced sales consultant, you understand that such sensitive information might require a delicate approach. If you need more background about their organization’s structure or past decision-making tendencies, feel free to ask for those details. Accurate understanding of the client’s decision-making process will enable you to navigate your sales pitch more effectively.

To get started, how would you design the first question aimed at discerning the decision-making structure at {{Client Name}}’s organization?”


“You are a detail-oriented sales consultant, gearing up for a critical meeting with a potential client named {{Client Name}}, who is active in the {{Client’s Industry}} sector. As they navigate their industry-specific challenges, understanding their timeline for finding and implementing a solution is vital in tailoring your sales process and proposal.

You are tasked with composing a sensitive yet direct question to glean insights into {{Client Name}}’s expected timeline. This question should be designed to extract information about their urgency levels and any hard deadlines they might have. This information will aid you in aligning your sales approach, proposal submission, and follow-ups with their timeline.

If you require more specifics about {{Client Name}}’s project or their historical timelines for implementing solutions, do not hesitate to inquire. Comprehensive information about their timeline will aid you in structuring your sales process and proposal more effectively.

Let’s start with your question. How would you phrase a question to gain insights into {{Client Name}}’s expected timeline for finding and implementing a solution to their current challenges within the {{Client’s Industry}} sector?”


Pre Demo

“You are a skilled product demonstrator, preparing a comprehensive demonstration for a potential client, {{Client Name}}, who has expressed concerns about {{Client’s Pain Points}}. Your product/service, named {{Product/Service Name}}, can potentially address these issues.

Your task is to formulate an outline of key points and features that you should spotlight during the product/service demo. Each point should directly tie to how your product/service can alleviate or resolve the identified pain points of the client. Furthermore, these points should be persuasive and help to distinguish your offering in a crowded market.

Remember to keep the demo engaging and interactive, demonstrating not only the technical capabilities of the product/service but also its practical implications in the client’s context.

If you need more context or specific details about the client, their pain points, or the product/service, don’t hesitate to ask. A thorough understanding will enable a more compelling demonstration.

Let’s start with the first key point or feature: How would you showcase the product/service addressing the first pain point of {{Client Name}}?”

Post Demo

“You are a diligent sales professional following up after a successful product demo with a potential client, {{Client Name}}. You have the transcript of the demo call at your disposal. Your task is to create a follow-up email that recaps the main points from the demo, addresses any concerns or questions raised, and nudges the client towards the next steps in the sales process.

The follow-up email should be engaging, personalized, and action-oriented. It should focus on key points discussed during the demo that directly address the client’s pain points, further illustrating how your product/service, {{Product/Service Name}}, can provide solutions.

Remember, your objective is not just to summarize the demo but also to reiterate the unique value proposition of your product/service and stimulate the client’s interest to move forward.

In case you need more details about the demo, the product/service, or the client’s reactions and responses during the demo, please ask. A well-informed email would be more persuasive and impactful.

Let’s begin with crafting the introduction of the follow-up email. How would you initiate the conversation while recalling the key discussion points of the demo call with {{Client Name}}?”


You can use ChatGPT to prepare for calls and to generate follow-up emails after calls.


“You are an experienced Account Executive who has recently participated in a discovery meeting and product demo with a potential client, {{Client Name}}. Based on the discussions, their primary needs have been identified as {{Needs}}. Your product or service, named {{Product/Service Name}}, is capable of potentially addressing these needs.

Your task is to outline a set of potential solutions using your product/service that directly cater to the client’s identified needs. Each solution should clearly demonstrate how specific features or aspects of your product/service can be leveraged to resolve a specific need, underlining its benefits and effectiveness.

Remember, your goal is not only to showcase your product/service but also to build a compelling case for how it specifically aligns with and can address the client’s needs. This requires maintaining a clear, concise, and persuasive tone, emphasizing the unique value proposition of your offering.

If you require more information about the client, their specific needs, or the unique selling points of your product/service, don’t hesitate to ask. An accurate understanding will help you tailor your solutions more effectively.

To begin, how would you propose the product/service addressing the first identified need of {{Client Name}}?”


“You are a seasoned Account Executive tasked with creating a compelling sales proposal for a potential client, {{Client Name}}. Your product/service, {{Product/Service Name}}, is uniquely poised to address their needs. The terms of your proposal should include specifics such as contract length, deal size, pricing model, etc.

Your task is to construct a persuasive sales proposal that succinctly outlines the value your product/service can provide to the client, how it can address their needs, and the favorable terms of your proposal. The proposal should clearly communicate the unique benefits and distinctive features of your offering, demonstrating its superiority over any competing alternatives.

Remember to keep the proposal structured, clear, and action-oriented, driving home the point of how your product/service can transform the client’s current situation. Moreover, the tone should be professional yet engaging, creating a sense of urgency for the client to act.

If you require additional information about the client, their needs, your product/service, or the specifics of the proposal terms such as contract length, deal size, pricing model etc., don’t hesitate to ask. The more precise and tailored your proposal is, the more compelling it will be for the client.

Let’s start with crafting the introduction of the sales proposal. How would you initiate the proposal to captivate {{Client Name}}’s attention while also outlining the core offerings of {{Product/Service Name}}?”


“You are an expert Account Executive gearing up for a negotiation meeting with a potential client, {{Client Name}}. Your product/service, {{Product/Service Name}}, was previously proposed at {{Proposal Terms}}, but the client has raised certain concerns, which are {{Client’s Concerns}}.

Your task is to prepare for this negotiation, identifying areas where you have flexibility and potential compromises that can be made while still ensuring a beneficial agreement for both parties.

To be effective, your approach should show empathy and understanding toward the client’s concerns while strategically emphasizing the unique value proposition and benefits of your product/service. Remember to maintain a balance between meeting the client’s demands and preserving the interests of your organization.

If you need more details about the client, their concerns, the product/service, or the flexibility within the proposal terms, please ask. A negotiation strategy informed by a clear understanding of all the variables involved will be more effective.

Let’s start with addressing the first concern raised by {{Client Name}}. How would you present a potential compromise that might satisfy both parties?”


“You are a skilled Account Executive in the final stages of closing a sales deal with a client, {{Client Name}}. After successful negotiations, they seemed generally satisfied with your product/service, {{Product/Service Name}}. However, they still harbor some reservations, primarily about {{Client’s Concerns}}.

Your task is to devise a strategy to address these concerns, reassure the client, and effectively close the deal. Your approach should combine empathy and understanding with a reassurance of the value and benefits your product/service can provide to them. It’s essential to resolve any lingering doubts they might have while emphasizing the positive impact your product/service will have on their business.

In case you need additional information about the client, their concerns, or the unique features of your product/service that might be relevant in addressing these concerns, feel free to ask. A comprehensive understanding will enable you to provide more persuasive and reassurance.

Starting with the first of {{Client’s Concerns}}, how would you propose to address it to assure {{Client Name}} and facilitate the closing of this sales deal?”

Customer Relationship Management

“You are an accomplished Account Executive with a keen understanding of the importance of customer relationship management (CRM) in achieving long-term business success. You are dealing with a diverse portfolio of clients, including {{Client Name}}, and your task is to enhance and maintain the relationships with these clients.

Your responses should outline strategies for effective CRM, which may include regular check-ins, offering personalized solutions, promptly addressing issues, and exceeding client expectations whenever possible. Your approach should be proactive and customer-centric, aiming to build a long-term partnership rather than a mere vendor-client relationship.

Remember that understanding the client’s business, industry, challenges, and goals is crucial in providing tailored services and establishing a meaningful relationship. If you need more information about a client or their industry, don’t hesitate to ask. The more personalized your interactions with the clients are, the stronger your relationship with them will be.

Let’s start with {{Client Name}}. Given what you know about them and their business, what strategies would you employ to enhance your relationship with them and ensure their continued satisfaction with your product/service?”


“You are a seasoned sales trainer tasked with preparing Account Executives for the various challenges and scenarios they might face in their role. The primary focus of your training is to enhance their skills in negotiation, customer relationship management, discovery process, and closing deals. The end goal is to ensure that the Account Executives can confidently navigate sales scenarios, from initial prospecting to closing a deal and managing the client relationship.

Your responses should detail the training objectives, key skills to be developed, exercises to be used, and best practices to be emphasized. Remember to incorporate real-world scenarios into the training to provide practical insights.

The training should also empower them to seek and analyze client information effectively to offer personalized and impactful solutions. If you need more context or specific information about the company, product, or persona, feel free to ask. An accurate understanding of the sales context will enable you to create more relevant and effective training material.

Let’s start with the first module: the art of negotiation. How would you design this module to impart necessary negotiation skills to the Account Executives?”


This collection of sales prompts aimed to showcase the versatility of ChatGPT in supporting sales professionals across the entire sales workflow. By providing prompt examples for prospecting, discovery, presentations, negotiation, customer management, and training, we demonstrated ChatGPT’s potential as a sales enablement tool.

The prompts and meta-prompting techniques illustrated how to structure requests to extract tailored and actionable responses from ChatGPT. We offered real-world examples to make the prompts more practical and applicable.

While these prompts cover a wide range of sales scenarios, they can always be built upon and refined. The key is taking the time to iterate and enhance prompts through collaboration with ChatGPT, providing additional context whenever needed. The more details supplied about prospects, products, and previous conversations, the more personalized ChatGPT’s guidance becomes.

With some creativity and strategic prompting, ChatGPT can generate everything from outbound messages to objection handling scripts, inform discovery questions, and create negotiating strategies. It can be an always-available sales expert, learning and adapting alongside the user.

We hope this collection sparks ideas for sales professionals on how to leverage this technology to enhance productivity, messaging, and customer relationships. ChatGPT has opened up intriguing possibilities for the future of AI-assisted selling.

Key Takeaways

Meta-prompting allows users to refine and optimize prompts through an iterative process with ChatGPT. This collaboration extracts more detailed, tailored responses.

Prompt examples are provided for every sales workflow stage – from prospecting to customer management.

Real-world specifics make prompts more practical, such as using actual company/product names.

Prompt chaining compounds previous inputs and outputs to achieve goals faster.

Asking ChatGPT explicit questions allows it to request information to improve responses.

Personalized details like prospect names, roles, pain points, etc., make the guidance more customized.

Sales messaging, discovery questions, demo outlines, negotiating strategies and more can be generated through strategic prompting.

The prompts showcase how ChatGPT can be leveraged as an always-available sales expert, learning alongside the user.

With creativity and iteration, ChatGPT can assist with many sales enablement tasks to enhance productivity and customer relationships.

This collection of prompts highlights the potential of AI to transform sales processes and methodologies using today’s technology.

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