October 21, 2024
In our world of sales, staying sharp isn't just nice - it's necessary. And that's exactly why we're diving into this topic today. We're not here to state the obvious or rehash ‘Sales 101’. We know you've got the basics down. This is about taking what you already know and cranking it up to an 11.
Enter ChatGPT - your always-on sparring partner, ready to help you level up your game. Whether you're waiting for your next call or killing time at the airport, ChatGPT's got your back.
The objective is:
In this blog, you’ll find prompts that you can just copy paste (with a little fine-tuning) and use to roleplay with ChatGPT, the various situations that you’ll encounter as a sales rep.
To get a good mock session, you can follow some tips that we recommend you do pre, during, and post.
1. Pre:
You’ll need to provide chatGPT with as much detail and context as you can. Let’s discuss the basic requirements that every prompt will need:
2. During:
Give it your best & honest shot. This is your chance to A/B test those comeback lines without the pressure. Want to try a new way to handle that pricing objection? Go for it. Need to rework your value prop? This is your lab. You can keep iterating until you find your groove.
3. Post:
After any roleplay, don’t just shut your system & go on. Few things that you can learn further:
For the purpose of this blog, I’m going to talk about fictional situations with characters at fictional companies. Any resemblance to real life situations is purely coincidental.
Contextual Prompt: I’m speaking with Ryan, the VP of Sales at LogiTex, a SaaS company specializing in logistics management software for eCommerce businesses. Ryan is responsible for equipping his sales team with tools to improve efficiency, reduce churn, and close deals faster.
We’ve had several discussions and demos, and Ryan was ready to move forward until he raised a last-minute objection. He’s detail-oriented and focused on feature comparisons, and his main concern is that a competitor offers a native integration with their CRM tool, which automatically updates client fields after each interaction. The competitor is also cheaper, making Ryan hesitant, as he’s under pressure to justify every dollar spent with measurable improvements in sales performance.
Although he recognizes the value of Sybill’s broader AI-powered insights and automation, this one feature feels like a potential dealbreaker. Ryan’s company operates on tight margins, so cost efficiency is critical.
Goal: My goal in this roleplay is to overcome Ryan’s objection by highlighting Sybill’s long-term value, such as better follow-up timing, personalized insights, and workflow adaptability. I also want to showcase Sybill’s new webhook feature, which allows integration with any tool of his choice, overcoming the CRM limitation. Throughout the conversation, I’ll address his budget concerns with data and case studies to prove Sybill’s cost-efficiency and superior ROI over time.
I want you to roleplay this conversation with me. I will start the conversation and you can then continue, ask me hard questions, be skeptical, and embody the analytical personality of the Sales leader. I’ll start the conversation after you respond to me with "okay.”
Contextual Prompt: I’m speaking with Claire, the Director of Sales at FinWise, a fintech company providing B2B payment solutions. Claire has been in her role for over five years and is focused on growing the sales team while scaling operations in a competitive market. FinWise’s small sales team handles a high volume of complex, multi-stakeholder deals, making efficiency a top priority for Claire.
Claire first showed interest in Sybill after downloading our AI in Sales playbook and attending a panel discussion where one of Sybill's founders spoke. She’s interested in streamlining her sales processes but hasn’t committed to a trial or demo yet. Her team is stretched thin with a new product launch and ongoing projects, leaving little time to explore new tools. However, improving efficiency remains a critical priority.
Claire is practical and data-driven, often asking for hard evidence before making decisions. She’s cautious about adopting new technology, especially after past experiences with tools that failed to deliver the expected ROI.
Goal: In this roleplay, my goal is to reignite Claire’s interest by showing how Sybill can immediately address her team’s pain points, particularly in time management and prioritization. Focus on how Sybill’s AI can automate call summaries, follow-ups, and CRM updates, and emphasize how easy it is to set up. Highlight the quick, measurable results her team can achieve with minimal time investment, making Sybill the perfect solution for their busy schedule and need for efficiency.
I want you to roleplay this conversation with me. I will start the conversation and you can then continue, ask me hard questions, be skeptical, and embody the analytical personality of the Sales leader. I’ll start the conversation after you respond to me with "okay.”
Contextual Prompt: I’ve just completed a demo with Megan, the VP of Operations at CloudSync, a mid-sized SaaS company that helps organizations manage cloud infrastructure. Megan is responsible for equipping her team with the right tools to streamline client onboarding and manage customer success. During the demo, she was interested in Sybill’s ability to automate follow-ups and generate action items, but she expressed hesitation about whether her team would fully utilize all of Sybill’s features.
Megan’s concerns stem from her team’s familiarity with their current tools and the potential learning curve involved in adopting a new system. She’s worried that Sybill could become another underutilized tool, especially since CloudSync has had issues in the past with tools that didn’t integrate well or were too complex. Additionally, Megan is under pressure to improve operational efficiency without adding to costs.
Goal: In this roleplay, my goal is to follow up with Megan and directly address her concerns. I’ll emphasize Sybill’s ease of use, quick setup, and minimal learning curve to ensure smooth adoption by her team. I’ll also highlight the quick wins Sybill can deliver, such as automating follow-ups and summarizing calls, which will provide tangible results without adding extra workload. I’ll be prepared to share data and case studies from similar teams who have quickly realized the value of Sybill, reassuring Megan that it will seamlessly integrate into her team’s workflow and deliver immediate, measurable benefits.
I want you to roleplay this conversation with me. I will start the conversation and you can then continue, ask me hard questions, be skeptical, and embody the analytical personality of the Sales leader. I’ll start the conversation after you respond to me with "okay.”
Contextual Prompt: I’m on a call with David, a Sales Manager at eComPro, an eCommerce software company that provides B2B solutions for online retailers. David manages a team of 10 sales reps who are responsible for handling a high volume of inbound and outbound sales calls each week. His team is struggling with the sheer amount of manual work involved in tracking leads, taking notes during meetings, and following up with prospects. As a result, critical details often get lost, follow-ups are delayed, and opportunities slip through the cracks.
David’s primary goal is to improve his team’s efficiency without adding more tools that would increase their workload. He’s frustrated with how much time his reps spend on administrative tasks rather than selling. He’s also mentioned that his team is using several tools that don’t communicate well with each other, which creates even more inefficiencies.
David has heard good things about AI-powered tools but is skeptical about whether they would actually solve the problem.
Goal: My goal in this roleplay is to convince David that Sybill can help reduce his team’s workload and improve efficiency by automating much of the manual work they’re currently doing. I need to show how Sybill can automatically generate call summaries, take notes with next steps and update their CRM automatically, freeing up his reps to focus on selling. Also, explain how Sybill integrates with the tools they’re already using and won’t add more complexity. Use specific examples of how Sybill has helped other teams streamline their processes and close more deals faster.
I want you to roleplay this conversation with me. I will start the conversation and you can then continue, ask me hard questions, be skeptical, and embody the analytical personality of the Sales leader. I’ll start the conversation after you respond to me with "okay.”
Contextual Prompt: I’m nearing the end of a long sales cycle with Lisa, the CFO of Precision Services, a B2B services company. Precision Services provides consulting and project management solutions to large enterprises, and Lisa oversees all financial decisions related to new investments.
Over the past three months, I’ve had several discussions and demos with Lisa and her team, and they’ve shown a strong interest in Sybill. However, as the deal nears the finish line, Lisa has raised concerns about the long-term ROI of the platform. She needs to be certain that Sybill will not only improve her team’s efficiency but also deliver measurable cost savings or revenue growth.
Lisa is conservative with spending and highly data-driven. She’s been tasked with ensuring that any new tool will justify its cost through clear, quantifiable improvements in her team’s performance.
Goal: In this roleplay, my goal is to provide Lisa with the data and reassurance she needs to move forward. I plan to use case studies, ROI calculations, and examples of how Sybill has delivered long-term value to similar organizations. I want to focus on Sybill’s ability to help her team close deals faster, improve lead conversion rates, and reduce the time spent on administrative tasks while addressing Lisa’s specific concerns around cost and ROI.
I want you to roleplay this conversation with me. I will start the conversation and you can then continue, ask me hard questions, be skeptical, and embody the analytical personality of the Sales leader. I’ll start the conversation after you respond to me with "okay.”
Contextual Prompt: I’m on a quarterly check-in call with Tom, a Sales Director at DataPros, an enterprise software company that has been using Sybill for six months. Tom’s team has been utilizing Sybill’s core features, such as automated call summaries and CRM updates, but they haven’t explored the platform’s more advanced capabilities, like Pre-call Briefs and Deal AMA.
Tom is generally happy with Sybill and has seen an improvement in his team’s efficiency, but he’s not fully convinced that they need additional features. He’s focused on keeping costs under control and doesn’t want to pay for features his team might not use. However, from my data, I’ve identified that Tom’s team could significantly benefit from Sybill’s advanced capabilities.
Tom is a practical, results-driven leader who cares deeply about maximizing his team’s performance without overburdening them with unnecessary tools. He’s willing to invest more if it will directly lead to better results, but he needs clear evidence that the extra features will provide measurable value.
Goal: My objective in this roleplay is to convince Tom that upgrading to Sybill’s more advanced features will help his team improve their sales outcomes by providing deeper insights into customer behavior, learning how to improve their own pitch, prioritizing leads more effectively, and driving more conversions. I have data and examples to show how other customers have successfully leveraged these features to increase sales performance and ROI. I need to reassure Tom that these features won’t add complexity but will instead help his team work smarter and achieve better results with less effort.
I want you to roleplay this conversation with me. I will start the conversation and you can then continue, ask me hard questions, be skeptical, and embody the analytical personality of the Sales leader. I’ll start the conversation after you respond to me with "okay.”
Contextual Prompt: I’m speaking with Jen, the VP of Sales at MedTech Solutions, a healthcare technology startup. Jen has shown interest in Sybill but is hesitant to move forward due to budget concerns. She’s managing a small, resource-constrained sales team, and while she sees potential in Sybill’s AI capabilities, she’s not convinced that her team can justify the cost, especially considering they tend to have offline sales conversations as well.
Jen has mentioned that she likes how Sybill automates follow-ups and reduces administrative work for her team, but she’s still unsure whether the investment will pay off on the call upload feature. She’s also concerned that her sales reps are already overwhelmed with their current workload and might not have the time to learn a new tool, even if it could help them in the long run.
Jen needs reassurance that Sybill will integrate smoothly into her team’s existing processes & needs to be confident that the ROI from Sybill will be noticeable and measurable within the first few months of implementation.
Goal: In this roleplay, my goal is to address Jen’s concerns around budget and adoption. I need to emphasize how Sybill can help her team get quick wins by saving time on follow-ups, improving relationships with clients by removing note-taking during meetings, and automating administrative tasks. I can offer data or case studies showing how Sybill has delivered fast ROI for other small teams, especially in resource-constrained environments. I want to reassure Jen that Sybill will ease, not add to, her team’s workload, allowing them to focus more on selling and less on manual tasks.
I want you to roleplay this conversation with me. I will start the conversation and you can then continue, ask me hard questions, be skeptical, and embody the analytical personality of the Sales leader. I’ll start the conversation after you respond to me with "okay.”
Contextual Prompt: I’m speaking with Steve, the CEO of FleetSmart Solutions, a fleet management software company. Steve has a packed schedule and only has 10 minutes for this call, so he expects me to get straight to the point. As CEO, Steve’s primary focus is on driving revenue growth and ensuring that every investment his company makes directly contributes to that goal.
Steve is not interested in diving into the technical details of how Sybill works. Instead, he wants high-level insights into how Sybill will solve his company’s biggest challenges - specifically, improving his sales team’s performance and shortening the sales cycle. He’s also very budget-conscious and needs to know that any tool his company adopts will deliver measurable, fast results.
I know that FleetSmart’s sales team currently struggles with long sales cycles and inconsistent follow-ups. They’re using outdated tools that don’t provide much in the way of data-driven insights, and Steve is keen to improve their efficiency.
Goal: My goal in this roleplay is to quickly convey Sybill’s high-level value to Steve without getting bogged down in the details. I want my focus to be how Sybill’s AI can help his team shorten sales cycles, improve lead conversion, and drive revenue growth - all while fitting within the company’s budget. I need to be concise, focusing on outcomes rather than features, to keep the conversation within the 10-minute window.
I want you to roleplay this conversation with me. I will start the conversation and you can then continue, ask me hard questions, be skeptical, and embody the analytical personality of the Sales leader. I’ll start the conversation after you respond to me with "okay.”
Contextual Prompt: I’m speaking with Sarah, the Head of Procurement at GreenTech Innovations, a company that develops renewable energy solutions. Mia has been tasked with finding the best sales enablement tool for her company’s rapidly growing sales team. She’s interested in Sybill but is also evaluating several competitors, some of which offer lower prices.
Mia is practical and focused on getting the best deal for her company. She’s not just concerned about upfront costs - she also wants to make sure they get the most value out of the investment over time. Mia has mentioned that one of our competitors is offering a similar solution at a lower price, and she’s hoping I can either match or beat that price.
Mia is also concerned about long-term costs and wants to ensure that Sybill won’t come with unexpected add-ons or fees down the road. While she’s intrigued by Sybill’s AI capabilities, she’s trying to figure out if it’s worth paying more for features that might not be necessary for her team right now.
Goal: In this roleplay, my objective is to justify Sybill’s pricing by emphasizing the additional value it provides compared to the competitor’s cheaper solution. I need to show Mia that Sybill’s AI capabilities - such as deeper insights, precise note-taking, and more personalized follow-ups - will lead to better outcomes for her sales team, ultimately driving higher revenue and providing a greater return on investment. I should also reassure Mia that Sybill’s pricing is transparent, without hidden fees or extra costs.
I want you to roleplay this conversation with me. I will start the conversation and you can then continue, ask me hard questions, be skeptical, and embody the analytical personality of the Sales leader. I’ll start the conversation after you respond to me with "okay.”
Contextual Prompt: I’m speaking with Mark, the VP of Sales at PayFam Solutions, a financial technology company. Mark is evaluating several sales enablement tools for his team, and during our last conversation, he mentioned that he’s also considering a competitor that offers a specific feature he’s particularly interested in: automated lead scoring based on call analytics. This feature has caught his attention because it aligns with his team’s goal of prioritizing high-quality leads more effectively.
Mark is practical and results-oriented. He’s interested in any tool that can help his team close deals faster and improve lead management. However, he’s concerned that if he chooses Sybill, his team will miss out on the competitor’s lead-scoring feature, which he believes could give them a competitive edge.
Our previous discussions have highlighted Sybill’s strengths in areas like call summaries, AI-driven follow-ups, and CRM integration, but Mark is still stuck on the competitor’s lead-scoring advantage. He’s not fully convinced that Sybill offers something as valuable in that area.
Goal: My goal in this roleplay is to address Mark’s concerns about the competitor’s lead-scoring feature and show him how Sybill’s AI provides even greater value through its comprehensive approach to sales enablement. I need to emphasize how Sybill’s AI provides deeper insights into customer interactions with it’s Deal AMA feature, while also enabling personalized follow-ups, and non-verbal cue reading to help reps close more deals.
I want you to roleplay this conversation with me. I will start the conversation and you can then continue, ask me hard questions, be skeptical, and embody the analytical personality of the Sales leader. I’ll start the conversation after you respond to me with "okay.”
Practice till you gain confidence & adaptability, not just to know the ‘right responses’.
By running through these roleplay scenarios, you’re giving yourself the space to refine your strategies, test out new approaches, and sharpen the skills that will ultimately help you close more deals.
So, take these scenarios, make them your own, and run through them. The more you practice, the more natural these tough conversations will feel when they happen in real time.
Here’s to turning objections into opportunities and roleplay into real-world success. Happy selling!
In our world of sales, staying sharp isn't just nice - it's necessary. And that's exactly why we're diving into this topic today. We're not here to state the obvious or rehash ‘Sales 101’. We know you've got the basics down. This is about taking what you already know and cranking it up to an 11.
Enter ChatGPT - your always-on sparring partner, ready to help you level up your game. Whether you're waiting for your next call or killing time at the airport, ChatGPT's got your back.
The objective is:
In this blog, you’ll find prompts that you can just copy paste (with a little fine-tuning) and use to roleplay with ChatGPT, the various situations that you’ll encounter as a sales rep.
To get a good mock session, you can follow some tips that we recommend you do pre, during, and post.
1. Pre:
You’ll need to provide chatGPT with as much detail and context as you can. Let’s discuss the basic requirements that every prompt will need:
2. During:
Give it your best & honest shot. This is your chance to A/B test those comeback lines without the pressure. Want to try a new way to handle that pricing objection? Go for it. Need to rework your value prop? This is your lab. You can keep iterating until you find your groove.
3. Post:
After any roleplay, don’t just shut your system & go on. Few things that you can learn further:
For the purpose of this blog, I’m going to talk about fictional situations with characters at fictional companies. Any resemblance to real life situations is purely coincidental.
Contextual Prompt: I’m speaking with Ryan, the VP of Sales at LogiTex, a SaaS company specializing in logistics management software for eCommerce businesses. Ryan is responsible for equipping his sales team with tools to improve efficiency, reduce churn, and close deals faster.
We’ve had several discussions and demos, and Ryan was ready to move forward until he raised a last-minute objection. He’s detail-oriented and focused on feature comparisons, and his main concern is that a competitor offers a native integration with their CRM tool, which automatically updates client fields after each interaction. The competitor is also cheaper, making Ryan hesitant, as he’s under pressure to justify every dollar spent with measurable improvements in sales performance.
Although he recognizes the value of Sybill’s broader AI-powered insights and automation, this one feature feels like a potential dealbreaker. Ryan’s company operates on tight margins, so cost efficiency is critical.
Goal: My goal in this roleplay is to overcome Ryan’s objection by highlighting Sybill’s long-term value, such as better follow-up timing, personalized insights, and workflow adaptability. I also want to showcase Sybill’s new webhook feature, which allows integration with any tool of his choice, overcoming the CRM limitation. Throughout the conversation, I’ll address his budget concerns with data and case studies to prove Sybill’s cost-efficiency and superior ROI over time.
I want you to roleplay this conversation with me. I will start the conversation and you can then continue, ask me hard questions, be skeptical, and embody the analytical personality of the Sales leader. I’ll start the conversation after you respond to me with "okay.”
Contextual Prompt: I’m speaking with Claire, the Director of Sales at FinWise, a fintech company providing B2B payment solutions. Claire has been in her role for over five years and is focused on growing the sales team while scaling operations in a competitive market. FinWise’s small sales team handles a high volume of complex, multi-stakeholder deals, making efficiency a top priority for Claire.
Claire first showed interest in Sybill after downloading our AI in Sales playbook and attending a panel discussion where one of Sybill's founders spoke. She’s interested in streamlining her sales processes but hasn’t committed to a trial or demo yet. Her team is stretched thin with a new product launch and ongoing projects, leaving little time to explore new tools. However, improving efficiency remains a critical priority.
Claire is practical and data-driven, often asking for hard evidence before making decisions. She’s cautious about adopting new technology, especially after past experiences with tools that failed to deliver the expected ROI.
Goal: In this roleplay, my goal is to reignite Claire’s interest by showing how Sybill can immediately address her team’s pain points, particularly in time management and prioritization. Focus on how Sybill’s AI can automate call summaries, follow-ups, and CRM updates, and emphasize how easy it is to set up. Highlight the quick, measurable results her team can achieve with minimal time investment, making Sybill the perfect solution for their busy schedule and need for efficiency.
I want you to roleplay this conversation with me. I will start the conversation and you can then continue, ask me hard questions, be skeptical, and embody the analytical personality of the Sales leader. I’ll start the conversation after you respond to me with "okay.”
Contextual Prompt: I’ve just completed a demo with Megan, the VP of Operations at CloudSync, a mid-sized SaaS company that helps organizations manage cloud infrastructure. Megan is responsible for equipping her team with the right tools to streamline client onboarding and manage customer success. During the demo, she was interested in Sybill’s ability to automate follow-ups and generate action items, but she expressed hesitation about whether her team would fully utilize all of Sybill’s features.
Megan’s concerns stem from her team’s familiarity with their current tools and the potential learning curve involved in adopting a new system. She’s worried that Sybill could become another underutilized tool, especially since CloudSync has had issues in the past with tools that didn’t integrate well or were too complex. Additionally, Megan is under pressure to improve operational efficiency without adding to costs.
Goal: In this roleplay, my goal is to follow up with Megan and directly address her concerns. I’ll emphasize Sybill’s ease of use, quick setup, and minimal learning curve to ensure smooth adoption by her team. I’ll also highlight the quick wins Sybill can deliver, such as automating follow-ups and summarizing calls, which will provide tangible results without adding extra workload. I’ll be prepared to share data and case studies from similar teams who have quickly realized the value of Sybill, reassuring Megan that it will seamlessly integrate into her team’s workflow and deliver immediate, measurable benefits.
I want you to roleplay this conversation with me. I will start the conversation and you can then continue, ask me hard questions, be skeptical, and embody the analytical personality of the Sales leader. I’ll start the conversation after you respond to me with "okay.”
Contextual Prompt: I’m on a call with David, a Sales Manager at eComPro, an eCommerce software company that provides B2B solutions for online retailers. David manages a team of 10 sales reps who are responsible for handling a high volume of inbound and outbound sales calls each week. His team is struggling with the sheer amount of manual work involved in tracking leads, taking notes during meetings, and following up with prospects. As a result, critical details often get lost, follow-ups are delayed, and opportunities slip through the cracks.
David’s primary goal is to improve his team’s efficiency without adding more tools that would increase their workload. He’s frustrated with how much time his reps spend on administrative tasks rather than selling. He’s also mentioned that his team is using several tools that don’t communicate well with each other, which creates even more inefficiencies.
David has heard good things about AI-powered tools but is skeptical about whether they would actually solve the problem.
Goal: My goal in this roleplay is to convince David that Sybill can help reduce his team’s workload and improve efficiency by automating much of the manual work they’re currently doing. I need to show how Sybill can automatically generate call summaries, take notes with next steps and update their CRM automatically, freeing up his reps to focus on selling. Also, explain how Sybill integrates with the tools they’re already using and won’t add more complexity. Use specific examples of how Sybill has helped other teams streamline their processes and close more deals faster.
I want you to roleplay this conversation with me. I will start the conversation and you can then continue, ask me hard questions, be skeptical, and embody the analytical personality of the Sales leader. I’ll start the conversation after you respond to me with "okay.”
Contextual Prompt: I’m nearing the end of a long sales cycle with Lisa, the CFO of Precision Services, a B2B services company. Precision Services provides consulting and project management solutions to large enterprises, and Lisa oversees all financial decisions related to new investments.
Over the past three months, I’ve had several discussions and demos with Lisa and her team, and they’ve shown a strong interest in Sybill. However, as the deal nears the finish line, Lisa has raised concerns about the long-term ROI of the platform. She needs to be certain that Sybill will not only improve her team’s efficiency but also deliver measurable cost savings or revenue growth.
Lisa is conservative with spending and highly data-driven. She’s been tasked with ensuring that any new tool will justify its cost through clear, quantifiable improvements in her team’s performance.
Goal: In this roleplay, my goal is to provide Lisa with the data and reassurance she needs to move forward. I plan to use case studies, ROI calculations, and examples of how Sybill has delivered long-term value to similar organizations. I want to focus on Sybill’s ability to help her team close deals faster, improve lead conversion rates, and reduce the time spent on administrative tasks while addressing Lisa’s specific concerns around cost and ROI.
I want you to roleplay this conversation with me. I will start the conversation and you can then continue, ask me hard questions, be skeptical, and embody the analytical personality of the Sales leader. I’ll start the conversation after you respond to me with "okay.”
Contextual Prompt: I’m on a quarterly check-in call with Tom, a Sales Director at DataPros, an enterprise software company that has been using Sybill for six months. Tom’s team has been utilizing Sybill’s core features, such as automated call summaries and CRM updates, but they haven’t explored the platform’s more advanced capabilities, like Pre-call Briefs and Deal AMA.
Tom is generally happy with Sybill and has seen an improvement in his team’s efficiency, but he’s not fully convinced that they need additional features. He’s focused on keeping costs under control and doesn’t want to pay for features his team might not use. However, from my data, I’ve identified that Tom’s team could significantly benefit from Sybill’s advanced capabilities.
Tom is a practical, results-driven leader who cares deeply about maximizing his team’s performance without overburdening them with unnecessary tools. He’s willing to invest more if it will directly lead to better results, but he needs clear evidence that the extra features will provide measurable value.
Goal: My objective in this roleplay is to convince Tom that upgrading to Sybill’s more advanced features will help his team improve their sales outcomes by providing deeper insights into customer behavior, learning how to improve their own pitch, prioritizing leads more effectively, and driving more conversions. I have data and examples to show how other customers have successfully leveraged these features to increase sales performance and ROI. I need to reassure Tom that these features won’t add complexity but will instead help his team work smarter and achieve better results with less effort.
I want you to roleplay this conversation with me. I will start the conversation and you can then continue, ask me hard questions, be skeptical, and embody the analytical personality of the Sales leader. I’ll start the conversation after you respond to me with "okay.”
Contextual Prompt: I’m speaking with Jen, the VP of Sales at MedTech Solutions, a healthcare technology startup. Jen has shown interest in Sybill but is hesitant to move forward due to budget concerns. She’s managing a small, resource-constrained sales team, and while she sees potential in Sybill’s AI capabilities, she’s not convinced that her team can justify the cost, especially considering they tend to have offline sales conversations as well.
Jen has mentioned that she likes how Sybill automates follow-ups and reduces administrative work for her team, but she’s still unsure whether the investment will pay off on the call upload feature. She’s also concerned that her sales reps are already overwhelmed with their current workload and might not have the time to learn a new tool, even if it could help them in the long run.
Jen needs reassurance that Sybill will integrate smoothly into her team’s existing processes & needs to be confident that the ROI from Sybill will be noticeable and measurable within the first few months of implementation.
Goal: In this roleplay, my goal is to address Jen’s concerns around budget and adoption. I need to emphasize how Sybill can help her team get quick wins by saving time on follow-ups, improving relationships with clients by removing note-taking during meetings, and automating administrative tasks. I can offer data or case studies showing how Sybill has delivered fast ROI for other small teams, especially in resource-constrained environments. I want to reassure Jen that Sybill will ease, not add to, her team’s workload, allowing them to focus more on selling and less on manual tasks.
I want you to roleplay this conversation with me. I will start the conversation and you can then continue, ask me hard questions, be skeptical, and embody the analytical personality of the Sales leader. I’ll start the conversation after you respond to me with "okay.”
Contextual Prompt: I’m speaking with Steve, the CEO of FleetSmart Solutions, a fleet management software company. Steve has a packed schedule and only has 10 minutes for this call, so he expects me to get straight to the point. As CEO, Steve’s primary focus is on driving revenue growth and ensuring that every investment his company makes directly contributes to that goal.
Steve is not interested in diving into the technical details of how Sybill works. Instead, he wants high-level insights into how Sybill will solve his company’s biggest challenges - specifically, improving his sales team’s performance and shortening the sales cycle. He’s also very budget-conscious and needs to know that any tool his company adopts will deliver measurable, fast results.
I know that FleetSmart’s sales team currently struggles with long sales cycles and inconsistent follow-ups. They’re using outdated tools that don’t provide much in the way of data-driven insights, and Steve is keen to improve their efficiency.
Goal: My goal in this roleplay is to quickly convey Sybill’s high-level value to Steve without getting bogged down in the details. I want my focus to be how Sybill’s AI can help his team shorten sales cycles, improve lead conversion, and drive revenue growth - all while fitting within the company’s budget. I need to be concise, focusing on outcomes rather than features, to keep the conversation within the 10-minute window.
I want you to roleplay this conversation with me. I will start the conversation and you can then continue, ask me hard questions, be skeptical, and embody the analytical personality of the Sales leader. I’ll start the conversation after you respond to me with "okay.”
Contextual Prompt: I’m speaking with Sarah, the Head of Procurement at GreenTech Innovations, a company that develops renewable energy solutions. Mia has been tasked with finding the best sales enablement tool for her company’s rapidly growing sales team. She’s interested in Sybill but is also evaluating several competitors, some of which offer lower prices.
Mia is practical and focused on getting the best deal for her company. She’s not just concerned about upfront costs - she also wants to make sure they get the most value out of the investment over time. Mia has mentioned that one of our competitors is offering a similar solution at a lower price, and she’s hoping I can either match or beat that price.
Mia is also concerned about long-term costs and wants to ensure that Sybill won’t come with unexpected add-ons or fees down the road. While she’s intrigued by Sybill’s AI capabilities, she’s trying to figure out if it’s worth paying more for features that might not be necessary for her team right now.
Goal: In this roleplay, my objective is to justify Sybill’s pricing by emphasizing the additional value it provides compared to the competitor’s cheaper solution. I need to show Mia that Sybill’s AI capabilities - such as deeper insights, precise note-taking, and more personalized follow-ups - will lead to better outcomes for her sales team, ultimately driving higher revenue and providing a greater return on investment. I should also reassure Mia that Sybill’s pricing is transparent, without hidden fees or extra costs.
I want you to roleplay this conversation with me. I will start the conversation and you can then continue, ask me hard questions, be skeptical, and embody the analytical personality of the Sales leader. I’ll start the conversation after you respond to me with "okay.”
Contextual Prompt: I’m speaking with Mark, the VP of Sales at PayFam Solutions, a financial technology company. Mark is evaluating several sales enablement tools for his team, and during our last conversation, he mentioned that he’s also considering a competitor that offers a specific feature he’s particularly interested in: automated lead scoring based on call analytics. This feature has caught his attention because it aligns with his team’s goal of prioritizing high-quality leads more effectively.
Mark is practical and results-oriented. He’s interested in any tool that can help his team close deals faster and improve lead management. However, he’s concerned that if he chooses Sybill, his team will miss out on the competitor’s lead-scoring feature, which he believes could give them a competitive edge.
Our previous discussions have highlighted Sybill’s strengths in areas like call summaries, AI-driven follow-ups, and CRM integration, but Mark is still stuck on the competitor’s lead-scoring advantage. He’s not fully convinced that Sybill offers something as valuable in that area.
Goal: My goal in this roleplay is to address Mark’s concerns about the competitor’s lead-scoring feature and show him how Sybill’s AI provides even greater value through its comprehensive approach to sales enablement. I need to emphasize how Sybill’s AI provides deeper insights into customer interactions with it’s Deal AMA feature, while also enabling personalized follow-ups, and non-verbal cue reading to help reps close more deals.
I want you to roleplay this conversation with me. I will start the conversation and you can then continue, ask me hard questions, be skeptical, and embody the analytical personality of the Sales leader. I’ll start the conversation after you respond to me with "okay.”
Practice till you gain confidence & adaptability, not just to know the ‘right responses’.
By running through these roleplay scenarios, you’re giving yourself the space to refine your strategies, test out new approaches, and sharpen the skills that will ultimately help you close more deals.
So, take these scenarios, make them your own, and run through them. The more you practice, the more natural these tough conversations will feel when they happen in real time.
Here’s to turning objections into opportunities and roleplay into real-world success. Happy selling!
