AI Leader of the Month: Sharon Easterling, Founder of Upskillz LLC 10-16-25

Summary

Becker Business Podcast Summary

Episode: AI Leader of the Month: Sharon Easterling, Founder of Upskillz LLC
Date: October 16, 2025
Host: Scott Becker
Guest: Sharon Easterling, Founder of Upskillz LLC

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Episode Overview

This special episode celebrates Sharon Easterling as Becker Business’s AI Leader of the Month. Sharon, founder of Upskillz LLC, shares her journey into healthcare technology, the mission behind Upskillz, and her perspective on preparing the workforce for AI-driven transformation. The discussion dives into the intersection of AI, continuous learning, human judgment, and how to foster resilience and adaptability through rapid change.

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Key Discussion Points & Insights

1. Sharon Easterling’s Journey and the Mission Behind Upskillz

• Sharon's background is in healthcare revenue cycle, consulting in medical coding and clinical documentation improvement (CDI).
• She observed a persistent knowledge gap among health information professionals regarding emerging technologies.
• Upskillz was founded to "increase foundational knowledge of AI" in healthcare and leverage professionals’ workflow expertise for AI implementation.

“I wanted to create an avenue to help increase their foundational knowledge of AI, but also pull on what they needed...that’s what's needed in AI right now.”
— Sharon Easterling ([01:36])

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2. Upskillz’s Offerings and Practical Solutions

• Custom AI products and micro-training to teach:
  • Foundational AI concepts
  • Prompting algorithms
  • Workflow optimization for healthcare professionals
• Tools that help integrate AI while safeguarding compliance, accuracy, and trust, especially outside of sensitive (HIPAA) environments.

“A big part of what we do is support systems that help people integrate AI without compromising your compliance or your accuracy or your trust.”
— Sharon Easterling ([02:59])

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3. Balancing Human Judgment and Automation

• Focus on augmenting, not replacing human roles.
• AI streamlines repetitive tasks and surfaces patterns while allowing people to focus on decision-making and empathy.
• Examples: AI career coach GPTs that support daily workflow and personal professional development.

“It's not about replacing people...It's about protecting our brain for what it's best in, right? The decision making, the empathy, the analysis.”
— Sharon Easterling ([03:56])

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4. Advice for Professionals Looking to Stay Relevant

• Start with small, consistent steps; you don't need to master everything at once.
• Learn enough to ask better questions—curiosity is key.
• Build learning communities and sandbox environments using de-identified data to experiment and develop low-risk AI skills.

“Learn enough to ask better questions...join a community so you can get some of that foundational knowledge.”
— Sharon Easterling ([05:15])

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5. Surprising Lessons from Leadership and Teamwork

• Sharon is encouraged by the willingness of professionals to experiment and learn.
• Emphasizes that teamwork is essential for adopting and mitigating the impact of AI.

“I've found that with this new process, people are learning that they have to lean on others some more. This is a team process.”
— Sharon Easterling ([06:46])

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6. Innovation and the Future of Work

• Sharon is excited about “Secura,” Upskillz’s automated software to mitigate denials and automate appeals for providers.
• Upcoming: A new website (upskillsadvisors.com) featuring online courses and a certification prompt program.
• The true potential is unlocked when people innovate with AI tools.

“Once people really realize what AI has the ability to do, innovation happens. And that is very exciting to me.”
— Sharon Easterling ([08:10])

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7. Habits and Mindset for Resilience

• Make time for reflection (journaling, walking, white space in calendar).
• Focus on processing change, not just reacting to it.
• Reframe failure as a learning opportunity to stay grounded and curious.

“I also have learned to reframe failure...ask yourself, what did it teach me and how can I apply that going forward?...That shift...takes [judgment] to being more curious.”
— Sharon Easterling ([09:18])

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8. Mentorship and Leadership Challenges

• Mentorship shaped Sharon’s career; both formal and informal mentors were crucial.
• Advocates for designing supportive, not performative learning environments.
• Stresses the importance of collaboration and providing safe spaces for honest feedback and questions.

“If we can design learning environments that are supportive and not performative, we can create more pathways for people to grow.”
— Sharon Easterling ([11:09])

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Notable Quotes and Moments

• On the goal of Upskillz:
  “We needed a way to, to increase that knowledge with our professionals so they can step into AI and impact those workflows because they know the business and they know the work.”
  ([01:17])
• On learning AI:
  “Have a sandbox...where you can go in and just figure out how AI works and how you can use that in your day to day...build real skills in a low risk setting.”
  ([05:33])
• On the importance of community:
  “Don't isolate yourself. You know, bring in your team, have a learning partner, join a community...”
  ([05:19])
• On innovation:
  “Once people really realize what AI has the ability to do, innovation happens.”
  ([08:10])
• On resilience:
  “I try to use those things to process the change versus trying to react to the change...reframe failure...”
  ([09:03])

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Important Timestamps

• 00:42 – Sharon describes her journey and inspiration for Upskillz
• 02:45 – Overview of Upskillz’s solutions for businesses
• 03:53 – Balancing people and AI in technology and training
• 05:05 – Advice for professionals to remain relevant and upskill
• 06:39 – Lessons learned from leadership and building a team
• 07:40 – Exciting current and future projects at Upskillz
• 08:59 – Habits and mindset for resilience and adaptability
• 10:25 – Mentorship, leadership challenges, and building supportive environments
• 11:44 – How to connect with Sharon and learn more about Upskillz

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Connect with Sharon Easterling & Upskillz

• Follow Sharon Easterling on LinkedIn
• Websites: upskillsaccelerator.org, upskills.org, [upskillsadvisors.com](https://upskillsadvisors.com—coming soon)
• Email: [e-mail]

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Tone & Takeaways

Sharon’s approach is collaborative, empathetic, and focused on empowerment. Her optimism about AI’s impact in healthcare is grounded in the need for strong foundational knowledge, continual upskilling, and community-based learning. The episode is both inspirational and practical, equipping listeners with concrete advice on navigating technological change while emphasizing the enduring value of human judgment and resilience.

Transcript

[A]

This is Scott Becker with a special episode of the Becker Business and the Becker Private Equity Podcast. We're thrilled today to be joined by a brilliant leader. We're joined today by Sharon Easterling and Sharon's the founder of the start of Upskill, Upskills and we're going to talk today about Upskills and what they do, technology and training solutions, AI and a lot more. Sharon, we are proud to have featured this month as our AI Leader of the Month and a remarkable leader. Sharon, can you take a moment and tell us a little bit about your journey and what inspired you to start Upskills and what problem you're set out to solve? What are you trying to do?

[B]

I'm so glad to be here today. So I have been in revenue cycle for a number of years, health care and as I stepped out, I was doing some consulting in the revenue cycle round with medical coding and CDI and I started to see a disconnect, right. We have so many seasoned professionals out there in health information, medical coding, compliance and cdi and I noticed that they weren't necessarily being equipped with all the knowledge they needed because of how things were happening so fast with technology. So as I saw the need with the progression of the initial AI natural language processing, I knew that there was going to be some impact as things started to progress much faster. We knew workflows, we knew documentation, but we really wasn't expanding the knowledge within different individuals in healthcare. They weren't getting some of that knowledge that they needed to step into a more AI powered world. So when ChatGPT came out, I immediately saw, oh my gosh, we're going to move much faster. And so we needed a way to, to increase that knowledge with our professionals so they can step into AI and impact those workflows because they know the business and they know the work. And so I wanted to create an avenue to help increase their foundational knowledge of AI, but also pull on what they needed, what they knew from workflows and how businesses really operate. That's what's needed in AI right now.

[A]

Could not agree more. And talk a little bit about what exactly Upskills does and how you help organizations adapt to this rapid change in the workplace. Talk a bit about what exactly you're doing and how you helping individuals adapt to this rapid change.

[B]

So, you know, we're looking to build real learning tools and AI strategies that are going to support the real work out there. You know, we have custom AI products, micro training and educational frameworks that help teach foundational AI Help teach prompting algorithms and how to build workflows to help individuals within the healthcare industry move faster. A big part of what we do is support systems that help people integrate AI without compromising your compliance or your accuracy or your trust. For example, in documentation we help people with AI outside of HIPAA environments. You know, that's a concern right now. So helping them learn the mechanics of how AI works and how to apply that to their everyday work.

[A]

Thank you. And talk about some of the technology and the training solutions that you're working on that sort of blend people and AI and how do you sort of balance human judgment and automation? How do you work these things together?

[B]

Right? So you know, Scott, it's not about replacing people, right? It's about protecting our brain for what it's best in, right? The decision making, the empathy, the analysis there. So we're about surfacing information, identifying patterns and speeding up repetitive tasks. And we're doing that by building real AI tools, things that can help you in your career. Having a career coach, GPTs that can not only help you with your day to days, but help trigger some of those things that may be causing you to stumble. You know, help you figure out those next steps. And that's what AI is there for, to kind of lend a hand, not necessarily guide us throughout the entire process.

[A]

Thank you. And it's the world changes so rapidly. We see so many professionals, so many leaders at every level feeling anxious about keeping their skills relevant, staying current, knowing what to do. What advice would you give to people trying to keep themselves relevant, trying to upskill or reinvent themselves.

[B]

So first of all, you know, always smart to start small, right, and stay consistent in what you're doing. You know, we, there's so much out there with AI, we don't have to master everything all at once. So we always say, you know, learn enough to ask better questions, right? So you can have that growth there and definitely don't isolate yourself. You know, bring in your team, have a learning partner, join a community so you can get some of that foundational knowledge and be able to take those next steps. Another great starting point that we like to play with, Scott, is having a sandbox in an environment, an environment where you can go in and just figure out how AI works and how you can use that in your day to day, maybe using some de identified data. You know, these playgrounds, they give professionals, especially in health care, a way to build real skills in a low risk settings. So you can try pumps and explore tools and learn the basics to take the Next step.

[A]

Thank you. And remarkable what you're doing. Just an amazing leader and an amazing, thoughtful person about trying to mix sort of what's currently going on with the evolution and rapid expansion of artificial intelligence. When you look at things as you've been a founder and a leader, Sharon, what are some of the most surprising lessons that you've that have been surprising to you or what have you learned? What's been surprising as a founder and leader?

[B]

Absolutely. So what's been surprising to me is that there are a number of people out there that are really embracing AI and taking the next step and try to learn those things and, you know, do application with it. You know, coming from my background in leadership, I've always thought that it's important to partner with others, to learn and be able to take the next steps, to grow your company or grow your department or whatever that is. And I've found that with this new process, people are learning that they have to lean on others some more. This is a team process, and it's going to take all of us to be able to mitigate AI.

[A]

No, thank you. I think that's exactly right. And Sharon, when you look at sort of what's going on right now, what are you most excited about and most focused on as it comes to upskills and it comes to the future of work and learning?

[B]

Yeah. So, so much to be excited about right now, Scott. So one of the things is that we created Shakira. I partnered with our RCM healthcare solutions, and we've created Secura, who is an automated software, and she's helping mitigate denials. So this is automating the appeal process for providers. So I'm very excited about that as well as I have a new website coming, upskillsadvisors.com which is going to have all the courses there that people will be able to take. So that's important, along with that certification prompt program. And we're going to be able to take people to the next level. And I can't wait to see what they build. Scott, I say that all the time. Once people really realize what AI has the ability to do, innovation happens. And that is very exciting to me.

[A]

Sharon, we talk a lot about resilience and reinvention and staying sharp and being adaptable. Those qualities in this time of rapid change are more important than ever. Are there any habits or mindset shifts that you use or think about to keep you resilient, to keep you sort of being adaptable, and advice that you'd give to others Absolutely, Scott.

[B]

You know, one is definitely making time for reflection, you know, reflecting on where you are now, where you have been, definitely looking at where you want to go. Whether you're doing that through journaling or, you know, having walks or, you know, white space on your calendar so you can get your thoughts together. Those things are very crucial. And I try to use those things to process the change versus trying to react to the change. Right. Because it's all around us. And I also have learned to reframe failure if something hasn't worked exactly as you thought it should be, having that resilience to go forward and ask yourself, well, what did it teach me and how can I apply that going forward? I think that shift is, you know, helps us with our judgment and takes it to being more curious and helps us to stay grounded even when things aren't necessarily moving as fast as we want them to.

[A]

Scott, thank you. No, I couldn't agree with that more. And talk a bit about. You do a lot of mentoring and mentorship.

[B]

What.

[A]

What advice or how do you think about mentoring people today? And also maybe what leadership challenges have you overcome? So thoughts on mentorship and also leadership challenges that you've overcome and think about?

[B]

Yeah, you know, mentorship is huge. It shaped my entire career, whether it be that CFO or that CEO that I work with, or even staff or comrades that I've worked with within some of my associations. Some of those mentorships, of course, were formal and I learned things, and others were just people who offered honest advice and feedback and made space for my grove. So today I actually like to create those same types of spaces. And I think that people are gonna be able to get that in upskills, where they're gonna be able to get that mentorship, whether it be through training, events we have, or through building tools. I think it's great to collaborate with others as we build. So it's not always about a person necessarily. Sometimes it's just a resource source, a nudge, or just having a safe space to ask questions. Scott, you know, if we can design learning environments that are supportive and not performative, we can create more pathways for people to be able to grow.

[A]

Could not agree more. And, Sharon, where can people find out more about upskills? Where can they reach you and can they follow you on LinkedIn?

[B]

Please follow me on LinkedIn. Lots is happening there. You can stay up to date about the release of the new website, but you can find me on upskills accelerator.org or upskills.org and love to chat with you or infoupskills.org Sharon Easterling, who we're.

[A]

Featuring this month as the AI leader of the Month. Just a remarkable, remarkable person and leader. Sherry, we are so thankful for you joining us today. Thank you very much for being on the Becker Private Equity and the Becker Business podcast. It is always remarkable to visit with you.

[B]

Absolutely. Scott, love being here and love everything you're doing with Becker's.

[A]

Thank you so much.