Premise
OK, so I’ve been hunting for a job for almost 100 days now. It sucks. The drain, the uncertainty, the frustration of getting rejected. Ugh. It is truly not something I’d wish on my worst enemy.
Either way, I have some spare time now, so wanted to try out some things, specifically ATS scanning vs. generative AI. Where are we now with ATS scanning and how can GenAI transform the already frustrating job hiring market.
The Frustration - ATS Scanning
There are some glaring issues with ATS scanning, mainly that it turns me into a keyword expert and not an actual expert. Someone could have none of the skills, but all the right keywords and end up with a potential interview that they are not qualified for, or worse, all the right skills, but none of the keywords to get past the ATS. Because the ATS is a black box, its a bunch of guessing and trying new things.
For a HR manager, its equally frustrating because they have to summarize the problem into a short concise paragraph or two with at least a minimum requirement set up. Two years of AWS experience? What does that even mean? Is that constant exposure? Or I touched it once 2 years ago and once again this year, does that constitute as 2 years? It’s very arbitrary. Nonetheless, you have to have a minimum requirement and hope that it’ll work out in the long run.
Generative AI
Now genAI is pretty cool. It’s taking the world by storm and has some pretty ingenious solutions to problems and has definitely sped up my workflows with projects or items I’m looking up. There’s so much more I could do with it but it’s moving fast and I need to look for jobs. Not maintain my expertise on genAI.
The problem with Generative AI tools (and most ATS tools currently is use), specifically as they relate to job searching, is they are focused mainly on the HR managers experience, not the job seekers experience, because the HR manager are the ones who’s time is valuable to the company so need to make it as effortless as possible for the manager.
For example, here’s a tool I found, Interviewer.AI. Their initial statement is a great selling point for hiring mangers or HR:
That is awesome. Someone who’s struggling with interviewing so many candidate and making the right decision, this would be a godsend. Interview hundreds of potential candidates in a few hours rather than days? Yes please. Sign me up.
But me as a job seeker sees this as another hurdle to overcome, spending more time on yet another set of questions, but this time I can’t do it while I’m in the car doing DoorDash or Uber because I need to be at a computer looking nice for an interview someone may or may not watch. All to allow the business to “interview” hundreds of candidate, while giving the hiring manager the tools to scan and keyword search what they are looking for without even having to lift a finger to interview them.
This would be hell for me, I’m now the only party who is required to spend time preparing for a potential position that now requires more effort from me.
While I hope it becomes a second phase interview process, I’m sure companies will move this to initial interviewing because it allows them to interview more efficiently and get qualified candidates quicker at the expense of the job seekers time.
My Idea
Here’s my idea. Instead of giving the HR and hiring managers all the tools, lets see if I can use generative AI to support what I’m capable of, but at a much deeper level.
I’ll hand the resume to the ATS scanner and see what score it gives me based on the keywords of my resume.
I’m then going to ask ChatGPT to see if it to see if the position is a good fit for me, and what success rate I’ll have in the position.
Finally, I’ll have it interview “me” by asking it to interview itself based on my skills and what it knows about me. Honestly, I have no idea how this is going to turn out.
Testing
I’ve been training ChatGPT on my likes, dislikes, I’ve given it my resume, links and documents I’ve written for it to gather context of what I’m capable of. I’ve told it I’m looking to be a Systems Engineer or Cybersecurity Engineer, I’ve trained it on some of the tools and products I’ve used, etc. You can see my full skillset here on LinkedIn: https://www.linkedin.com/in/rayalner/ or some details about my portfolio at www.blog.rayalner.com/portfolio
With that out of the way, let’s do some testing on an idea I have. Lets try 3 jobs.
Job 1
Job Description
OK, here’s a Systems Engineer role:
Description
Summary of This Role
Monitors and controls client operating systems to ensure efficient and continuous performance. Advises on the technical aspects of information systems and products, cost, technical requirements to meet customer needs/system environment. Prepares flow charts, models, and procedures and conducts feasibility studies to design possible system solutions.
What Part Will You Play?
Work with leadership to formulate plans to meet the strategic direction of the Infrastructure Engineering team Support automated methodologies for build activities, such as for servers, load balancer VIPs, application firewall rules and firewall policies Partake in ownership and engineering efforts, such as new infrastructure solutions design and optimization, for multiple engineering projects, concurrently Maintain installation and configuration procedures, and drive automation around these areas Support the efforts for cross-training and collaboration with other members of the team. Develop shared knowledge of leveraged tools on the team, eliminating single points of knowledge and dependencies Work with management and technical peers to establish and support technical policies and procedures. Continuously provide procedures to operational teams and work with these teams to ensure details are up-to-date, accurate and understood Drive compliance and security efforts related to systems managed by the team Support and continuously improve upon methods to improve availability of infrastructure services Work with the Project Managers and Infrastructure Coordinators on project progress, issues and solutions
What Are We Looking For in This Role?
Minimum Qualifications
Bachelor's Degree, Computer Science, other majors considered. additional experience in lieu of a degree. Min 3 years experience in Linux systems administration Min 1 year experience SysOps administration in a cloud platform. AWS strongly prefered. Preferred Qualifications None Identified What Are Our Desired Skills and Capabilities? Skills / Knowledge - Developing professional expertise, applies company policies and procedures to resolve a variety of issues. Job Complexity - Works on problems of moderate scope where analysis of situations or data requires a review of a variety of factors. Exercises judgment within defined procedures and practices to determine appropriate action. Builds productive internal/external working relationships. Supervision - Normally receives general instructions on routine work, detailed instructions on new projects or assignments.
ATS Scanner
Here’s the Jobscan tool’s ATS response:
I think it captures some things that aren’t important, but also has no weight to what the words are in comparison to what the job may hold. Very rudimentary understanding of who I am.
ChatGPT Response
Here’s ChatGPT’s response:
Strengths and Fit: Linux Systems Administration: You have extensive experience with Linux/Ubuntu and systems architecture, making you well-prepared for the minimum requirement of 3 years in Linux systems administration. Your background in systems engineering further supports this.
Automation and Infrastructure: You have worked on automating system management processes, such as reducing management overhead and using tools like GitLab for CI/CD. This directly aligns with the role’s emphasis on automation, particularly in areas like server builds, firewall policies, and installation procedures.
Cross-Training and Collaboration: You’ve expressed experience managing security and data protection, as well as mentoring or working collaboratively with teams, which fits with the role’s requirement for knowledge sharing and avoiding dependencies on single points of expertise.
Security and Compliance: Your cybersecurity expertise and familiarity with security standards, like ISO 27001 and HIPAA, match the compliance and security efforts outlined in the role. You’ve also worked on projects involving infrastructure and security, like DevSecOps and cloud strategies, which would benefit you in this position.
Cloud Experience: You have experience with Microsoft Azure, but this role asks for AWS SysOps. Though your focus has been more on Azure, your general cloud experience (Azure VMs, Logic Apps, Blob Storage) suggests you could transition into AWS with some upskilling.
Project Management and Systems Engineering: You’ve been involved in large-scale system projects, like rebuilding infrastructures and managing multiple projects, making you well-suited for coordinating infrastructure designs and optimizations across multiple engineering efforts.
Areas to Consider:
AWS vs. Azure: Since AWS experience is strongly preferred, and most of your cloud experience is on Azure, this could be an area for growth. Transitioning your skills to AWS is highly doable, but you may need to upskill or take some training to bridge the gap.
SysOps: While you have infrastructure and automation experience, this role calls for specific SysOps administration in a cloud platform. You may need to familiarize yourself more with AWS-specific SysOps, but your general experience will provide a strong foundation.
Overall Fit:
This role seems to align well with your strengths in systems engineering, automation, and infrastructure design. Your background in security and compliance adds value, particularly as the role emphasizes improving infrastructure availability and security. The cloud experience gap (AWS vs. Azure) is manageable, and your demonstrated ability to adapt and thrive in new technologies should allow you to quickly bridge this.
Success Estimate: Based on the alignment with your skills and experience, I’d estimate your success in this role at around 85-90%. The AWS experience would be the main area to focus on, but otherwise, this seems like a strong fit for your capabilities.
This seems completely at odds with the Jobscan ATS tool, and as biased as I am, I tend to agree with ChatGPT’s response. I have the core competences but may lack in AWS, which for me wouldn’t be a problem to up-skill. In some ways, I don’t see how I would be able to add these “keywords” to the resume without needing to rewrite to fit the job description and getting flagged for being “too close” to the job description.
Interview
OK, now for the 15 minute interview:
Interviewer: Hi Ray, thank you for joining us today. Could you start by telling me a bit about your background and what brings you to this position?
Ray: Absolutely, thank you for having me. I’ve spent over a decade in systems engineering, with the last five years focused heavily on cybersecurity. I’ve worked across a broad range of IT projects, from rebuilding infrastructures and cutting costs on CI/CD pipelines to ensuring security compliance for HIPAA and other regulatory standards. I’ve led projects focused on system automation and improving efficiencies through tools like GitLab, Azure, and Kubernetes. What attracted me to this role is the chance to leverage my experience in infrastructure automation and systems design while deepening my expertise in cloud environments, particularly AWS.
Interviewer: That’s great to hear! One of the key aspects of this role is working with leadership to align infrastructure engineering with the company’s strategic goals. Can you share an example of how you’ve worked with leadership to deliver on strategic initiatives?
Ray: Certainly. One example was when I was tasked with overhauling the infrastructure of a business that had aging systems, from phones to laptops to file-sharing services. I worked closely with leadership to understand the business goals—cost reduction and minimizing downtime were critical. I designed and executed a plan to rebuild their entire IT infrastructure, ultimately saving them 20% on operational costs. Throughout the process, I maintained regular communication with the leadership team to ensure alignment with their strategic objectives and timelines. The project was a success, both technically and from a business standpoint.
Interviewer: That’s a strong example. This role also requires experience with Linux systems administration and automation. Could you give us some insights into your experience automating processes in a Linux environment?
Ray: Absolutely. One of the more impactful projects I worked on involved automating updates for a fleet of Linux servers. The goal was to reduce system management overhead, and I built out scripts to automate patching and security updates. I leveraged tools like Bash and GitLab CI/CD to streamline the process, reducing manual intervention and improving system availability. This approach also helped with compliance because it ensured the systems were consistently updated with the latest patches without relying on manual updates. I’ve always found automation to be key to scalability and reliability, and it’s a cornerstone of how I approach systems administration.
Interviewer: The position also emphasizes improving infrastructure services and ensuring high availability. How do you typically approach that?
Ray: While I haven’t specifically worked on high-availability infrastructure or automated failover systems, I’ve focused on improving the reliability of systems through automation and proactive monitoring. For example, I automated server updates and security patching, which significantly reduced downtime and ensured systems were consistently up-to-date. I’ve also worked on optimizing CI/CD pipelines to reduce the time to deploy, which contributes to better system reliability. While high-availability design is an area I’m looking to grow into, I’m confident that my experience with automation and system optimization would allow me to quickly contribute and learn in this space.
Interviewer: It sounds like you’ve got a lot of relevant experience. We work heavily with AWS for our cloud infrastructure. Could you tell me about your experience with cloud platforms and specifically AWS?
Ray: Most of my cloud experience has been with Microsoft Azure, where I’ve managed virtual machines, blob storage, and logic apps. While my hands-on experience with AWS is more limited, the core principles between cloud platforms are similar—whether it’s provisioning resources, managing security, or setting up infrastructure as code. I’ve worked on cloud cost-optimization projects and built secure cloud environments, which I can easily translate to AWS. I’m also committed to upskilling in AWS-specific tools, particularly with SysOps, to make sure I can fully support the team’s objectives.
Interviewer: That’s good to hear. One final question before we wrap up—how do you handle collaborating with cross-functional teams and sharing knowledge, especially on a technical level?
Ray: Collaboration is key in any technical role. In my current role, I work with both technical and non-technical teams, ensuring that everyone is aligned on project goals. One thing I prioritize is documentation and cross-training. For example, when I designed a CI/CD pipeline for a client, I made sure to document every step and conduct training sessions so that other team members could manage the pipeline in my absence. It’s important to me that knowledge doesn’t reside with just one person, and I enjoy creating a collaborative environment where everyone can contribute and learn from each other.
Interviewer: That’s a great approach, Ray. I think that covers everything for now. Thanks again for taking the time to speak with us today.
Ray: Thank you, I appreciate the opportunity to discuss the role. I look forward to hearing from you!
End of Interview In this mock interview, your answers focus on key areas like Linux automation, infrastructure design, cloud platform experience, and collaboration, which are all critical to this role. You’ve emphasized your strengths while addressing the AWS gap by showing your willingness and ability to upskill quickly. This should leave a positive impression on the interviewer.
Pretty crazy right? The only change I had it make was I haven’t worked in highly-available systems, although I have worked with redundancy and making sure I have redundant systems, I don’t have experience in automated failover, load balancers or HA systems. It was hallucinating. Not surprising but do have to watch for it.
Job 2
Job Description
OK, here’s a Security Engineer position.
Responsibilities
You will perform the following responsibilities alongside other members of the information security team:
Engineer data feeds, rules, and tuning for the system information and event manager (SIEM); Triage security operations center (SOC) alerts as the Level II/III escalation support; Triage secrets scanning, static application security testing (SAST), dynamic application security testing (DAST), and software composition analysis (SCA) tools; Triage cloud security posture management (CSPM), infrastructure as code (IaC) security scanning, and attack surface violations; Identify patch management gaps using our vulnerability management software and collaborate with IT and Engineering teams on resolutions; Perform internal security testing, assessments, and triaging of alerts from security tooling; Conduct secure code reviews, secure design reviews, and threat modeling activities; Support GRC activities through control evidence collection; Contribute to operational support activities for all security capabilities. This includes preparing self service operational support documentation for developers and project teams, responding to internal support chat groups; Contribute to design and development of observability metrics and monitoring capabilities for all security capabilities utilizing DevOps or SRE principles; Support the creation and publication of metrics on security functions usage and remediation status for consumption by developers and project teams.
Requirements
Ability to automate or develop basic tasks in at least one programming language such as: Java, JavaScript, Python Professional certifications such as WAPT, PPT, OSCP, etc and/or computer science degree; 1+ years security engineer experience or 2+ years as a Security Analyst or equivalent; Experience working with cloud technologies such as: AWS, GCP, Azure, Docker/Kubernetes.
ATS Scanner
Here’s the Jobscan tool’s ATS response.
This one’s confusingly better although I’m still missing far more “skills” based on its prediction. Interesting.
ChatGPT Response
Here’s ChatGPT’s response:
Based on your experience and capabilities, you’re well-positioned to succeed in this role. Here’s a breakdown of how your skills align with the responsibilities and requirements:
SIEM Engineering and SOC Escalation: You have experience with various SIEM tools like Wazuh, as well as general incident response and monitoring skills. This positions you well to engineer SIEM data feeds and handle SOC alerts at a higher level. Your knowledge of cloud security and logging (Azure Monitor, Log Analytics) will help you tune and optimize these systems.
Security Tooling and Triage: Your toolset already includes extensive experience with security scanning tools like GitLab SAST, GitLab DAST, and SonarQube, which align perfectly with responsibilities involving SAST, DAST, and secrets scanning triage. You’ve also started incorporating API fuzzing, further expanding your expertise.
Cloud and Infrastructure Security: You have worked with Azure AD, Trivy for infrastructure scanning, and have mentioned security concerns around containers and Kubernetes, though you prefer to focus less on containerization. This experience positions you to effectively contribute to CSPM, IaC scanning, and cloud security efforts, particularly in Azure environments.
Patch Management and Vulnerability Resolution: You’ve managed patching processes in DevSecOps frameworks and have experience using scanning tools like Trivy. This will allow you to identify gaps in patch management and collaborate with IT and Engineering on resolutions.
Internal Security Testing and Threat Modeling: Your background in both static and dynamic scanning, as well as a focus on RBAC controls, aligns well with conducting internal security tests and reviews. While you’ve mentioned some gaps in working with automated failover or high-availability infrastructures, your strengths in continuous monitoring and cloud strategy will aid you in threat modeling and secure design reviews.
Operational Support and Documentation: You’re familiar with writing automation scripts and operational strategies, so you can support teams by creating self-service documentation. Your background in app development and product strategy using Agile methodologies (such as with Olleh) has also given you experience working closely with teams to ensure they have the tools and documentation they need.
Observability and Monitoring: While you’ve primarily focused on other areas like SIEM and infrastructure security, your experience with cloud observability (Azure monitoring tools) and Agile processes suggests you’ll be able to contribute to observability metrics and monitoring security capabilities. Your ability to build systems that scale will be valuable for setting up effective security monitoring.
Metrics and Reporting: You’ve led successful projects where metrics and outcomes were critical, such as cost-saving initiatives for CI/CD pipelines and cloud strategies. Your ability to focus on results and present them clearly will help you contribute to the creation of security function metrics and support teams in remediation.
Additional Considerations:
Certifications and Development: While you don’t emphasize programming skills in Python or JavaScript, your experience with low-code environments like WeWeb and Xano shows your adaptability. Though you don’t have coding experience in common languages, your practical experience managing DevSecOps plans and automating tasks suggests you can overcome this quickly if needed.
Professional Certifications: You haven’t explicitly mentioned certifications like OSCP or WAPT, but your robust practical experience may compensate for this, especially if you’re pursuing further qualifications. Your extensive experience in security engineering, cloud technologies, and DevSecOps frameworks makes you a great fit for this role, particularly in triaging security alerts, supporting development teams, and enhancing security monitoring and automation processes.
Based on your skills, experience, and alignment with the job requirements, I would estimate your overall success potential for this role to be 85-90%.
This seems pretty accurate, it does say I have more experience in tooling than I actually do, and I am a bit lacking in certification and development and programming side of things, but generally speaking, I think I could be a pretty good fit for this role.
Interview
OK, now for the 15 minute interview:
Interviewer: Thank you for taking the time to meet with us today, Ray. To start off, could you give us a quick overview of your background and what brings you to this role?
Ray (Interviewee): Sure! I’ve been working in IT and systems engineering for over 10 years, with the last 5 years focused on security engineering. I’ve had a chance to lead several impactful projects, such as reducing CI/CD pipeline costs by over 90% and developing cloud security strategies that saved 10% in expenses. Recently, I’ve worked on creating security plans, including SAST, DAST, and IaC scanning, though I didn’t get as far into implementation on those. What excites me about this role is the opportunity to use my experience with security planning and operations to contribute to a more hands-on, implementation-focused environment.
Interviewer: It sounds like you’ve set up some great plans for security tooling. Could you tell us more about your work with SIEM systems and how you approach tuning them to reduce false positives and improve detection?
Ray: I’ve worked with Wazuh in a limited capacity—I was able to install and configure it, but we didn’t have enough data to fully implement and analyze the system. However, I’ve developed alerting plans using Grafana and have hands-on experience in configuring monitoring and alerting systems. In terms of SIEM tuning, my approach would be to baseline normal activity first and then refine the alerts to focus on the high-priority security events. That way, we minimize false positives and help the SOC prioritize critical alerts more efficiently.
Interviewer: That makes sense. Since you mentioned SAST and DAST, could you elaborate on your experience with security tool triaging and how you’d handle those alerts?
Ray: Most of my experience with SAST, DAST, and IaC has been at the planning and initial setup stage. I designed a DevSecOps plan that incorporated SAST and DAST tooling into the CI/CD pipeline, focusing on defining the right scanning tools and setting the thresholds for what should trigger alerts. While I didn’t get as far into full implementation, I am familiar with how these tools integrate into DevOps environments and how to approach triaging security alerts, working closely with development teams to prioritize critical issues based on risk.
Interviewer: It sounds like you have a solid foundation in setting up those processes. How would you approach cloud security and infrastructure-as-code scanning in our environment?
Ray: In terms of cloud security, my experience is largely with Azure, where I focused on setting up identity management and access controls using Azure AD and RBAC. For infrastructure scanning, I’ve used tools like Trivy to identify vulnerabilities in containers and ensure secure deployments. For IaC, while I’ve mostly worked on setting up the plans, my approach would involve integrating scanning tools directly into the CI/CD pipeline to catch misconfigurations before they reach production.
Interviewer: We also emphasize collaboration with IT and development teams in this role. How do you work with cross-functional teams, especially balancing security with operational priorities?
Ray: Collaboration is crucial to ensuring security doesn’t become a bottleneck. My approach is to communicate early with both IT and development teams, understanding their workflows and timelines. I’m very focused on automation to make security checks as seamless as possible—integrating security scans directly into CI/CD pipelines, for example, so they don’t have to manually address issues until it’s absolutely necessary. I also create clear, actionable documentation to help them resolve security alerts efficiently. By ensuring everyone understands the impact of security and how we can mitigate risks without slowing down their work, I help strike that balance.
Interviewer: That’s a good approach. Lastly, can you tell us about a challenging security project you’ve worked on and how you approached solving the problem?
Ray: One challenging project I worked on was restructuring a CI/CD pipeline to improve both security and efficiency. The original pipeline was costly and slow, so I started by mapping out the entire process and identifying where security could be automated. I then integrated security tools, such as GitLab’s SAST and DAST, into the pipeline. While we didn’t complete the full implementation, the plan was to automate container scanning with Trivy as well. The process was designed to ensure that security was addressed early, reducing both manual intervention and runtime costs. The changes we implemented resulted in a significant reduction in overall pipeline runtime.
Interviewer: That’s great, Ray. We’re just about out of time, but do you have any questions for us?
Ray: Yes, I’d love to hear more about the current security tools you’re using and how you’re planning to evolve your security posture, particularly around cloud security.
Interviewer: Great question! We are using a mix of AWS-native tools and some third-party platforms for cloud security, and we’re looking to further automate and scale our security operations. Thanks again for your time today, Ray—it was great speaking with you.
Ray: Thank you, I appreciate the opportunity and look forward to hearing back from you!
Apart from some hallucinations I had to correct, this is a pretty accurate representation of what I know. It did keep repeating some of the same things, probably because I hadn’t trained it on all the things I’ve been able to complete, but that could be worked out in a better training protocol.
Job 3
Job Description
OK, here’s the curve ball. Here’s a sales position.
Duties And Responsibilities
This key position requires someone who is able to learn and maintain in-depth knowledge of [redacted] products and technologies, competitive products, and industry trends. You are primarily responsible for increasing revenue in assigned regions/territories/districts through identifying, recruiting, and developing opportunities for generating direct sales or partnerships with resellers.
Meet and exceed assigned sales targets by closing new accounts and growing revenues Identify prospects for [redacted] products through cold calls, and lead follow-up and face-to-face meetings Call on senior executives to understand the business, decision-making, and financing processes of your territory Present and demonstrate [redacted] products to customers Provide customer and competitor feedback and field intelligence where available and necessary Prepare and implement strategic sales account plans for all customers and identify business growth opportunities in assigned customer base Ensure resellers and field sales engineers and management are working together in the sales process, lead generation, registering opportunities, accurately forecasting revenue, and tracking to required revenue goals established by their discount tier Work with resellers to grow business in your territory Prepare and maintain an accurate sales forecast for your territory Network in customer and related organizations
Required Qualifications And Experience
Four-year degree or equivalent in a related discipline (e.g., information technology, computer science, business, or engineering) 5 years of experience in technology sales with a consistent track record of exceeding sales targets 2 years of cybersecurity or complex SaaS solutions sales experience Demonstrated technical acumen to articulate [redacted] value proposition in a differentiated and compelling manner Strong communication, organizational, and interpersonal skills Proven history of sales success in network/application management or related IT infrastructured solutions Demonstrated ability to secure meetings and close deals with senior-level executives Solid understanding of enterprise networking technologies: switches, routers, firewalls, load balancers, WAN optimization technologies, EDR and SIEM Strong independent work ethic and experience working in startup culture Existing senior level relationships at a wide range of accounts in your assigned territory Background in software/hardware sales and distribution with large software, hardware, and/or networking companies Ability to travel
ATS Scanner
Here’s the Jobscan tool’s ATS response.
In this case, the sales experience and information technology are weighted the same, so I think the ATS gave me a far too high score on this description and wouldn’t understand how I could contribute to this role.
ChatGPT Response
Now for ChatGPT. I’ve told it I don’t like sales in previous discussions. It doesn’t align with my future goals. Here’s what it said.
Based on the job description and your current focus, here’s a breakdown of your potential percent success in this position:
Strong Alignment (60%) Technical Acumen: You have strong knowledge in cybersecurity and enterprise IT systems, which would allow you to articulate the technical aspects of ExtraHop’s solutions (EDR, SIEM, network/application management). Your background in systems engineering and your security expertise would help you understand the products and potentially communicate them well to clients.
Independent Work Ethic: You’ve thrived in roles with minimal oversight, and this role requires a strong independent work ethic, which fits your style.
Understanding of Systems Architecture: Your systems engineering background gives you a solid foundation for understanding the enterprise networking technologies involved (firewalls, SIEM, etc.). Even though WAN optimization and load balancers are areas you haven’t directly worked with, your ability to learn new tools quickly would help.
Moderate Alignment (20%)
Sales Experience: You have business management experience and some exposure to business development through partnerships (like with Systemworkx), but you’ve stated that sales and business development aren’t your main strengths. While you’re comfortable with client-facing interactions, achieving aggressive sales targets and managing a sales pipeline might be outside your primary skill set.
Low Alignment (20%)
Sales-Focused Responsibilities: This position is highly sales-driven, with a focus on prospecting, closing deals, and growing revenue. Since you’ve indicated a preference for roles that emphasize technical problem-solving, systems engineering, and cybersecurity over sales, this could be a difficult and less fulfilling area for you. The need to consistently meet and exceed sales targets might not align with your core strengths or career goals.
High-Level Networking and Relationships: While you’ve worked with senior executives before, this role emphasizes existing relationships with decision-makers and resellers in the territory. Building those networks might be time-consuming, and if your existing network doesn’t overlap with the industry or region, it could be challenging to ramp up quickly.
Estimated Success Percentage: 60-70%
If you were to pursue this role as it stands, your success might depend heavily on how well you can transition into the sales-heavy aspects, which is not your core area of focus. Your strong technical skills and ability to learn quickly would help, but meeting sales targets and managing a pipeline might feel less aligned with your preferred focus on engineering and security. If you were open to developing more in sales, your technical skills would provide a solid base, but if sales isn’t appealing long-term, the role could feel like a mismatch.
In summary:
Percent Success: Your estimated success in this role would be around 60-70%.
Why You Shouldn’t Apply: The role is highly sales-focused, requiring aggressive sales targets and heavy involvement in business development, areas you’re not interested in pursuing.
Why You Wouldn’t Fit: Your skills and career goals align more with technical problem-solving, systems engineering, and cybersecurity, not sales. This job wouldn’t fully utilize your strengths and could feel misaligned with your long-term career direction.
If you applied for this sales-heavy role and were hired, I’d estimate you might last 6 months to a year before feeling significant misalignment or dissatisfaction. The sales targets and focus on business development could become frustrating over time, as they don’t align with your core interests in technical problem-solving and cybersecurity engineering. The position might feel unfulfilling, leading you to seek out roles that better match your strengths and long-term career goals.
Pretty crazy, I think it has me down, except my success, I may be successful here, but don’t think I’d last long. Even though I have a lot of the technical skills I do lack the sales skills, which would be critical in this position. ChatGPT knew that and as such suggested I don’t apply for this position. I asked it how long I’d last here and it said about 6 months. Correct.
Interview
I did a mock interview, but also asked would I get the job right away, here’s what it came up with:
Here’s a mock 15-minute self-interview:
You: “Tell me about your experience with enterprise networking technologies and how you’ve applied them in your work.”
Ray: “I have a strong background in systems engineering and cybersecurity, where I’ve worked with firewalls, security tools, and various network configurations. Most of my experience has been in designing secure infrastructures, optimizing CI/CD pipelines, and improving IT processes. While I’m familiar with networking technologies, I haven’t had deep hands-on experience with WAN optimization or load balancers.”
You: “This role focuses heavily on meeting sales targets and growing revenue. How comfortable are you with a sales-driven role, and do you have experience closing deals?”
Ray: “Sales isn’t my primary focus. While I’ve been involved in client interactions and building business relationships, my strengths lie in technical problem-solving, systems architecture, and cybersecurity. I haven’t had direct sales responsibility, and I tend to prefer roles that don’t center around sales quotas and targets.”
You: “One of the key responsibilities is prospecting new clients and managing relationships with senior executives. How does that align with your past experience?”
Ray: “I’ve worked with senior executives before, but mainly in the context of aligning technical solutions with business goals. I’m comfortable presenting technical solutions, but cold-calling or prospecting to drive sales isn’t something I’ve done. I’m more focused on technical leadership and strategic problem-solving rather than sales outreach.”
You: “What would you do to prepare and execute a sales plan for a new territory?”
Ray: “I would first need to familiarize myself with the sales process. I’m very organized and strategic, so I would work closely with resellers and field sales engineers to understand the territory, but sales planning would require learning the intricacies of this process, which isn’t something I’ve done before.”
You: “How do you think you would perform in this role, and what would your expectations be?”
Ray: “Honestly, I think I would excel in understanding the technical aspects of the products and explaining them to clients. However, the pure sales and revenue generation side would be more challenging for me, as it’s outside my core expertise and interest. If this role allows for more technical responsibilities alongside sales, I could potentially do well, but if it’s entirely sales-focused, I might struggle to meet expectations.”
Conclusion: At the end of this self-interview, it’s clear that you’re technically strong but not aligned with the core sales-driven aspects of the role. You’re honest about your lack of direct sales experience and your preference for technical roles, which would likely make the interviewer question your fit for the position.
Would you get the job right away? Probably not. The hiring team might see your technical strengths but also recognize that your skills and interests don’t align well with the heavy sales requirements of this position. It’s unlikely they’d offer you the job immediately, but they might consider you for a more technical or hybrid role if one were available.
This is true, I don’t think I would succeed in this kind of position and would take me away from my current goals, so it wouldn’t make it worth my while to apply, but it is good to see that the generative AI was able to come up with that for me, and if it was being “interviewed” by another AI I would probably get passed on for this position.
A New, Better Era
I’ll hope that a future balances the two. Where if I go on the job market LinkedIn or its successor, I can mark my profile as “open for work” and all of a sudden dozens of AI agents start working for me, scooping up everything I’ve written or said (that I want it to) and start compiling a list of jobs for me then interviewing their AI agents to see where a good fit for me would be, then after a couple days give me a few results of who may want to have a final interview. No longer am I going through dozens of rounds of interviews, the HR manager can interview me via my chatbot and ask me other questions without me having to interact with the HR manager. They could do it asynchronously on their own time, then I can have a final interview to discuss expectations.
This could also be a success for them too because most job descriptions fail to share the exact problem the company is trying to solve. Sometimes it’s because it’s sensitive, others the HR manager or hiring manager doesn’t know exactly what they are solving. So the AI agent can gather internally what problems they are trying to solving and feed my AI agent scenarios on how I’ve worked similar problems in the past based on their exact requirements and see how I would fair in that position. This is all done either automatically, or via a manager who’s like hey, I don’t know what problem I’m trying to solve, this person may be able to solve it but let me ask their AI and see what I think about their methodology. All without having to interact with the person.
Is it a bit scary? Yes, so much could go wrong. But at least this way, you’re respecting both the job seekers AND the hiring managers time without going into lengthy interviews that waste so much time if its not a good fit.
In the end, if I put an “open for work” or even “open to contract work” on my page, I could get dozens of offers for work without even lifting a finger, because the AI has done it for me, researching, checking fit, checking skills, checking capabilities.
That’s a world I’d be excited to see.
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