An Interview With Chad Silverstein
Professionally, there are many uses for AI in the workplace. For SEO professionals, AI can analyze search trends, suggest keywords, and optimize content for search engines. Paid ad performance, including bidding and targeting, can be analyzed and optimized in real time. AI can compile and visualize marketing performance data for better decision-making. However, it’s a tempting and slippery slope. As companies use automation techniques to get a “personalized email message” or social media post to the best target audience, users use AI to summarize their email inboxes and social feeds. Which means… AI is now talking to AI.
In the ever-evolving and never-ending landscape of business, staying ahead of the curve is a prerequisite for success. Artificial Intelligence (AI) has gone from being a futuristic concept to a daily business tool that executives can’t ignore. In this interview series, we would like to talk with business leaders who’ve successfully integrated A.I. into their operations, transforming their companies in the process. I had the pleasure of interviewing Charles Orlando.
Charles Orlando is an accomplished, innovative technology leader, serial entrepreneur, and five-time best-selling author with nearly 30 years of diversified B2B, B2C, and SaaS industry experience. He specializes in building and scaling SaaS companies in terms of revenue, processes, and teams. As the Chief Marketing Officer at Galorath Incorporated, Orlando is responsible for driving all marketing strategy and go-to-market activities — including demand generation, marketing operations, product marketing, public relations, and brand — and strategizing and executing new market opportunities, including artificial intelligence.
Thank you so much for doing this with us! To set the stage, tell us briefly about your childhood and background.
My childhood, shaped by socioeconomic challenges, instilled in me a commitment to fostering equitable and inclusive environments, a long-standing respect for diversity, and the symbiotic relationship between positive change and growth. Growing up as a second-generation American, I witnessed barriers faced by marginalized communities and the determination required to overcome them. These experiences formulated and fostered personal and professional resilience, empathy, and a nuanced awareness of how social, cultural, and economic factors affect the ability to succeed — understandings that now guide my research, professional pursuits, and my quest to leave the world a better place than I found it (as trite as that might sound).
My professional background is split between technology and psychology, each informing the other. One facet comprises a broad mix of technology innovation and rapid expansion and growth into uncharted tech territories for both rising and established tech companies. The other leverages qualitative and quantitative research to understand human dynamics and interpersonal relationships through a real-world examination of the intersection where technology, communication, and relationships collide.
It’s been a fascinating and insightful journey. I’ve learned not only about people and business but also about myself. This has helped me find my place as a leader, manager, and innovator. But more importantly, it’s helped me evolve into a version of myself who builds highly effective teams that are empowered as individuals and trust each other.
What were the early challenges you faced in your career, and how did they shape your approach to leadership?
Today, marketers seem very siloed as specialists in a particular marketing function — demand generation, communications, product marketing, sales enablement, etc. I came up through the ranks during a time rife with change and demanded that marketers understand and own the complete marketing process. While I still have an affinity toward strategic communications and product marketing, I’ve held positions across all marketing functions in various vertical markets and operated in the weeds across programs and campaigns. To wit: I’ve conducted market segmentation and analysis and market opportunity assessments, researched and executed integrated go-to-market plans, operated as a creative director, attended press checks for printed collateral, formulated and executed integrated campaigns across radio, TV, outdoor, and digital, defined and evaluated personalized journeys to reach and convert prospects and customers, and researched, defined, and sold new solutions in the field of generative artificial intelligence. These activities help define me as a well-rounded executive with a wealth of experience and a leader who understands the challenges teams face when executing. Moreover, these experiences have ensured that I not only understand failure — and the necessity of failure to fuel long-term growth and success — but also allowed me to pass on an essential notion to my teams as they experience challenges: you will win some, and you will learn some.
Coupled with these experiences, I’m a husband and father. The shifting dynamics of family life and all the challenges and variables accompanying building and maintaining a life with others have ensured that I understand how teams are comprised of individuals with personal experiences and lives outside of the office. This reality helps keep me centered as I engage with colleagues and direct reports, ensuring I put my humanity above my business goals.
We often learn the most from our mistakes. Can you share one mistake that turned out to be one of the most valuable lessons you’ve learned?
As a young manager, I made the mistake of expecting people to act and work like I do — projects needed to be executed and achieved the way I would do it. Needless to say, teams don’t operate that way, and I ended up hurting the people on the teams I was leading. Assigning expectations in this way doesn’t work for a couple of reasons. For people to execute at speed, they need freedom. That freedom is comprised of a feeling of empowerment to take informed risks and the safety of knowing that it’s okay if they fail. These notions create an air of inspiration for the individual and the team overall, ensuring people aren’t just monetarily motivated to perform but are emotionally engaged and bought into the process of success.
Today, I’m not just a leader and manager. I see myself more as a “strategic inspirationalist.” Yes, I drive the strategy, ensure goals are measured and hit, and own the outcome for my department and function in the company. However, I am dedicated to each team member — each person — maintaining a feeling of empowerment. In short, and in reflection of my mistake early in my career, I have a choice: I can manage how people address the path (the plan/strategy, the “how” something gets done), or I can manage the destination (the goal or achievement), but I can’t manage both, lest I alienate my team and leave them disconnected… or worse, contributing to their reason for departure.
A.I. is a big leap for many businesses. When and what first sparked your interest in incorporating it into your operations?
I’m finishing my master’s degree, focusing on the incorporation and impact of generative AI on the humanities at the university level. My research has informed my thesis and exposed broader implications and opportunities in other markets, including Galorath.
In high-stakes industries like manufacturing, military and defense, government, aerospace, and IT, you’re not just dealing with numbers; you’re managing risk, resources, and time on a massive scale. Moving at speed and incorporating historical project data at scale for multibillion-dollar defense contractors and government agencies is not just a need; in today’s global economy, where time is the actual, limited commodity, it’s a necessity to stay competitive and address the growing, shifting needs of the market. These realizations made me evaluate not when or how to incorporate AI into Galorath’s offerings but whether it should be.
Galorath is driven by three principles related to cost, schedule, risk estimation, and analysis: 1) Improving speed-to-market, 2) Increasing project accuracy and viability, and 3) Driving corporate profitability. This forced me to answer a strategic question: If generative AI can positively impact these guiding principles, how will it manifest itself, and what will the benefit be to the customer? This foundational approach to business and development ensured Galorath didn’t launch “an AI strategy.” Instead, we have a strategy within which AI is a significant component.
Today, ten months past the initial launch of our prototype and now moving to a proper beta, and after hundreds of conversations with users and companies, the Galorath team and our customers have realized how transformative it can be for informed strategic decision-making. But the challenges are significant. Because we aren’t just following the trending nature of AI, we are constantly adjusting, experimenting, and trying new approaches. Each effort is informed and tested, but due to the evolving nature of AI, we are always short of the event horizon. It’s an exciting place to be, where failure informs success, and success becomes a stepping stone to more profound learnings and use cases not yet seen.
AI can be a game-changer for individuals and their responsibilities. Can you share how you personally use AI and what are your go-to resources or tools?
AI is simultaneously amazing and scary and can be an effective tool. However, people need to realize that AI is only as good as the data it’s trained on and the quality of the prompt entered by the user. Bad input of either (or both) equates to bad output. Personally, I’ve used generative AI to synthesize and establish trendlines in data and research and found it to be a good listening partner (for lack of a better term). I can bounce ideas around, think out loud, and ideate quickly and easily. However, I’ve also experimented with how AI can be used nefariously.
Peruse the web briefly to see if individuals can use AI to research and write for them, and you’ll quickly discover cautionary tales of sanctioned lawyers and dire warnings for students who are nervous about using generative AI in any capacity. Even helpful tools like Grammarly (which I use) are now viewed by some organizations and universities as generative AI. The danger exists when critical thinking stops and the student/lawyer/user hands over thinking and evaluation to AI. (Read: enter prompt; receive response; copy and paste as “your” prose.)
Professionally, there are many uses for AI in the workplace. For SEO professionals, AI can analyze search trends, suggest keywords, and optimize content for search engines. Paid ad performance, including bidding and targeting, can be analyzed and optimized in real time. AI can compile and visualize marketing performance data for better decision-making. However, it’s a tempting and slippery slope. As companies use automation techniques to get a “personalized email message” or social media post to the best target audience, users use AI to summarize their email inboxes and social feeds. Which means… AI is now talking to AI.
On the flip side, what challenges or setbacks have you encountered while implementing A.I. into your company?
Over the past eighteen months, I have played a key role in integrating generative AI into a 45-year-old company’s offerings and internal workflows, leading the development of SEERai™ by Galorath. As the industry’s first agentic-enabled generative AI platform, SEERai securely and privately integrates a company’s historical project data with Galorath’s 45 years of project data and external large language models (LLMs) in real-time, allowing organizations to harvest evolving external insights — such as industry trends, regulatory updates, and supplier data — and harmonize them with internal datasets without manual training or human intervention. The result is dramatically enhanced decision-making accuracy, predictive analytics, and actionable intelligence while ensuring data privacy and corporate security oversight.
Naturally, we’ve encountered our fair share of ongoing challenges along the way, as AI is not a one-and-done solution. The AI landscape continues to evolve rapidly, and what is implemented today may feel outdated in a matter of months (or weeks). With SEERai, we’ve had to keep an open mindset and be prepared to pivot as new technologies emerge while allocating and reallocating resources for ongoing research and development.
Ensuring that the prompts users are inputting are effective has also been a challenge. The quality and specificity of a prompt can significantly influence the output and responses. For example, vague or overly broad prompts may lead to generalized responses lacking actionable detail, making the perception that SEERai isn’t knowledgeable. To combat this, we spend an exorbitant amount of time training users to craft prompts that align closely with the information they seek. It’s been a learning curve, but aligning prompts with specific project objectives has helped make SEERai’s output more relevant and valuable. Robust insights from SEERai come from an ongoing dialogue, allowing ideas to develop, evolve, and clarify.
AI also raises significant ethical questions. Prioritizing ethical AI practices has been vital in the SEERai development process. This means establishing clear guidelines, such as auditing data sources for bias or making AI models explainable. Transparency has also been key, ensuring customers and stakeholders understand how and why AI-powered decisions are being made.
Let’s dig into this further. Can you share the top 5 A.I. tools or different ways you’re integrating AI into your business? What specific functions do they serve and what kind of result have you seen so far? If you can, please share a story or example for each.
As I mentioned above, we expanded Galorath’s offerings last year with the launch of SEERai — the industry’s first advanced chat-based generative AI. SEERai is designed to assist digital engineers and cost estimation professionals in gaining action-oriented insights for projects and initiatives by unifying cost, schedule, and risk analysis into a single, scalable platform. Designed to evolve continuously by integrating new data and user feedback, SEERai stands distinct and squarely positions Galorath as an innovation leader and trailblazer in generative AI for digital engineering. Its integration into Galorath’s SEER platform allows users to input data in plain language to generate initial estimates and actionable scripts to plan and estimate projects with greater accuracy and efficiency. Currently used by enterprise organizations across multiple verticals, including multi-billion-dollar defense contractors and aerospace companies, SEERai is already demonstrating significant effectiveness in military, federal, and commercial settings.
Regarding how we apply AI internally for Galorath’s business processes… my answer is a transparent “Very sparingly.” Using automation or AI to assist, analyze, or harmonize data or resources to reach prospects effectively is smart business. It allows us to leverage technology to fuel scalability and effectively reach prospects and customers. However, we are careful not to replace our 45-year-old “personal touch” with an artificial or automated process that diminishes the Galorath brand and cheapens the user experience. The bottom line is that the only way we have lasted over four decades — and are now prepared for aggressive technology and international expansion — is by listening to our customers and staying abreast of market trends. That requires critical thinking and a subjective interpretation that gets internalized, discussed, tested, and tested again. AI can’t perform the critical thinking needed to add that human touch. And quite frankly, I wouldn’t want it to.
There’s concern about A.I. taking over jobs. How do you balance A.I. tools with your human workforce and have you already replaced any positions using technology?
AI is a powerful tool but cannot replicate genuine human connection or empathy. While I understand the concerns about AI impacting job displacements, when applied strategically and thoughtfully, AI should complement human capabilities, never replace them. Rather than a threat, I view AI as an opportunity. Given the daunting administrative tasks that no one likes, AI can alleviate many mundane duties that drag employees down, freeing up time to focus on higher-value projects and ultimately improving employee morale and customer interactions. “Boring AI” has the most value and can make the most profound impact, allowing humans to do what they do best: think and innovate.
A “Boring AI” example: a chatbot can answer common customer questions, but more complex issues must be escalated to human support team members. This balance improves efficiency without sacrificing customers’ trust. It’s a delicate balancing act between AI and the workforce. But when done right, AI and humans can join forces as a highly effective solution. For this to happen, leadership will remain key in ensuring a thoughtful approach to AI that balances the right amount of human intervention with technological innovation.
Looking ahead, what’s on the horizon in the world of AI that people should know about? What do you see happening in the next 3–5 years? I would love to hear your best prediction.
At the heart of the evolution of AI is generative AI — a powerful tool that is changing how we interact with and benefit from intelligent systems. Its ability to understand and generate content across industries opens a mass of opportunities, even for those less technical. However, like most new things, it isn’t perfect and comes with limitations and challenges. Over the next 3–5 years, AI will most likely become a central part of our daily lives. It will change how we work and create, help people achieve more with less, and continue to spark conversations around its impact and controversy. The ones who recognize its limitations, address concerns early on and understand how to effectively use it — whether on a personal or business level — will be vital to the evolution and ethical use of the technology.
If you had to pick just one AI tool that you feel is essential, one that you haven’t mentioned yet, which would it be and why?
It doesn’t exist at scale yet, but it’s what my master’s thesis is centered on: Integrating AI-powered personalization in English as a Second Language (ESL) learning. Creating compelling, personalized learning pathways has long presented a significant challenge in increasingly diverse classrooms, where learners differ widely in proficiency levels. Traditional instructional models often fall short, leading to disengagement among students who find content either too challenging or insufficiently stimulating. Recent advancements in artificial intelligence offer a solution through tools capable of providing real-time, adaptive feedback tailored to individual learners’ needs. In short, the students who excel are challenged, and the students who are struggling receive the remedial lessons they need to continue learning and growing — and instructors can stop offering a curriculum that attempts to impart knowledge only to those learners at the center of the bell curve while ignoring the outliers. This would require a balanced approach where AI supplements human instruction, helping educators manage diverse classrooms more effectively while maintaining the intellectual rigor essential to language mastery.
For the uninitiated, what advice would you give someone looking to integrate AI into their business and doesn’t know where to start?
Artificial intelligence is everywhere, and with generative AI promising the gamut of success, companies are eager to take advantage of its potential. My advice: don’t dive in headfirst without a clear view of what’s at the bottom. After spending over three decades helping SaaS and software companies scale and grow, I’ve watched businesses repeatedly latch onto new trends without considering whether they serve a strategic purpose and align with broader goals.
For those considering incorporating AI into their business, start with a clear business case, ensure the entire organization is engaged, anticipate challenges, and maintain a human touch. Additionally, I strongly advocate for rapid prototyping — test, refine, test, rebuild, test. Most important is the recognition that, for the foreseeable future, what is built today will be outmoded tomorrow; the industry is simply moving too fast.
Where can our readers follow you to learn more about leveraging A.I. in the business world?
LinkedIn profile: https://www.linkedin.com/in/charlesorlando
This was great. Thanks for taking time for us to learn more about you and your business. We wish you continued success!
About the Interviewer: Chad Silverstein is a seasoned entrepreneur with 25+ years of experience as a Founder and CEO. While attending Ohio State University, he launched his first company, Choice Recovery, Inc., a nationally recognized healthcare collection agency — twice ranked the #1 workplace in Ohio. In 2013, he founded [re]start, helping thousands of people find meaningful career opportunities. After selling both companies, Chad shifted his focus to his true passion — leadership. Today, he coaches founders and CEOs at Built to Lead, advises Authority Magazine’s Thought Leader Incubator.
Charles Orlando of Galorath Incorporated: How We Leveraged AI To Take Our Company To The Next Level was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.