Future-proofing means different things to different business leaders, but the desired outcome is always the same: the long-term wellbeing of the company.

By making strategic moves like investing in cutting-edge technologies and attracting top talent, companies can be better prepared to weather any storm, be it economic uncertainty, geopolitical unrest or a pandemic. 

The following eight leaders shared how they’ve transformed their businesses to promote success for many years to come — and how they’ll apply the lessons they’ve learned moving forward. 



Brad Stroh
co-founder and co-CEO • Achieve


Formally known as Freedom Financial Network, Achieve is a digital personal finance company whose financial solutions help people get on the path to a better financial future.


What is a key strategy, product, or plan you’ve put in place to transform your business, and why?

 In addition to our very empathetic and skilled member sales and support organization, we’ve focused on adding digital personalization, driven by data, tools and experiences for consumers. With the addition of digital personalization, we can ensure the right solution is put in front of the right consumer at the right time. And at Achieve, ultimately the consumer gets to choose how they work with us, whether via human support, digital only or a hybrid of the two. For us it’s about putting the consumer at the center of decision-making and meeting their specific needs to help them succeed with us as their partner. 


 How is that strategy paying off for you now? 

 We’re having record enrollment and the highest NPS scores we’ve had in the history of our company, showing our innovations drive meaningful impact and innovation to the consumers we serve. And we’re not done yet. We’re about to launch several apps so that we can offer service and support for free to consumers who might need a little more information about their debt or their budgeting before they feel ready to become a member.  


 What’s the most important lesson you’ve learned recently, and how do you hope to apply it to your business moving forward?

 For me, the most important lesson is to always believe in your team and your mission. Our mission is very clear: to empower everyday people to get on, and stay on, the path to a better financial future. As we’ve seen in the last few years, there are constant obstacles in business. From the pandemic to recent bank failures to macroeconomic conditions changing to inflation and recessionary concerns, there’s a lot of noise. It’s easy to get distracted by it all. Since we founded the company over 20 years ago, we’ve stayed true to our mission and kept the consumer in focus. We’re going to continue to maintain this as our North Star and our focus will drive our future success.




Dr. Angel Diaz
Discover Vice President of Technology Capabilities & Innovation • Discover


One of the most recognized brands in U.S. financial services, Discover is a direct banking and payment services company built on a legacy of innovation and customer service.


What is a key product, strategy or plan you’ve put in place to transform your business, or position you for the future and why?

We created a state-of-the-art internal learning platform called the Discover Technology Academy. Launched in September of 2021, the DTA was built to iteratively improve where information was housed, how it was connected and organized, and to become a home for everyone in the broader Discover community to contribute and consume knowledge. It’s a community built by engineers, for engineers, designed to help our engineering workforce upskill, grow their careers, and improve our products for our customers.

The public-facing Discover Technology Experience (technology.discover.com) launched in February of 2023, showcasing the people, processes, and technologies driving the digital products that help our customers achieve brighter financial futures. DTE grew out of the Discover Technology Academy, giving our engineers a space to share their knowledge with the world and learn from others. Our core technologies featured on DTE include open source, application development, agile, and cloud, with more technologies to come.


How is that strategy paying off for you now? 

Our engineering workforce is empowered to build their craft on a daily basis — learning new skills, connecting with SMEs, sharing their knowledge, and having the power of our collective knowledge at their fingertips. By having a workforce versed in the latest tech skills and committed to continuous learning, we can truly say we’re building the products that create better financial futures for our customers. The Discover Technology Academy has helped us accelerate our digital transformation toward becoming a product-centric organization. This mechanism has defined how we work while simultaneously improving the way we work. It’s built by Discover technologists, for Discover technologists.

Examples of engagement include 14,000+ active DTA community members. In a little over a year and a half, the DTA has seen more than 2 million page views. In the last year, DTA has hosted more than 300 learning events that have helped more than 50,000 attendees build their craft in a variety of emerging technology areas. At Discover, we get better every day, and we do that through the Discover Technology Academy. 

We’re taking this wealth of knowledge and sharing it with the broader technology community on the Discover Technology Experience (DTE). Our engineers have the opportunity to share their voice in ways that will help them become recognized as industry leaders and shape the future of technology both inside and outside of Discover.


What’s the most important lesson you’ve learned recently, and how do you hope to apply it to your business moving forward?

The most important lesson we’ve learned from building this platform internally and now sharing that knowledge externally through the Discover Technology Experience is that technologists learn as much by sharing their own expertise as they do from consuming others. We’ve seen so many of our developers start to build their eminence in the broader technology community. Our developers feel empowered here to build their craft and grow their careers in ways they never have.




Rob LoCascio
Founder and CEO • LivePerson


LivePerson’s conversational AI helps notable brands like HSBC and GM Financial connect with their audiences at scale. 


What is a key product, strategy or plan you’ve put in place to transform your business, or position you for the future and why?

This is a profound time in our history — both as a company and as witnesses (and creators of) the next big revolution in AI. As pioneers in using AI to drive business results for large enterprises, we have a giant opportunity ahead of us to make generative AI and large language models really work safely and productively for our customer brands. 

To position ourselves for the future, we recently took a step back and evaluated where we were focusing as a company. We saw a lot of growth during the pandemic, and like many tech companies, started chasing new revenue streams that weren’t sustainable. To be honest, we lost focus for a minute on our core mission of delivering better business outcomes through AI.  Recommitting to our core offering and figuring out how to use the latest tech, including generative AI and LLMs, to make our product even more valuable, has put us back on track for the long-term. 


How is that strategy paying off for you now? 

The excitement we’re seeing from our customer base, which is made up of the world’s biggest brands, is sky high. They are incredibly bullish about using AI to support their employees and customers. However, they are worried about using generative AI and LLMs since it’s so easy for those systems to hallucinate answers or go off the rails. Because they know we’re re-focused on what we do best, using AI to deliver real results, they know they can trust us to help them do it the right way.


What’s the most important lesson you’ve learned recently, and how do you hope to apply it to your business moving forward? 

Weve realized that it’s critical to step back every so often and look at the bigger picture. We want to solve some of the most complex problems brands are facing. It’s not about using LLMs to trick teachers into thinking you’ve done your homework, it’s about big picture issues like helping people manage their health and finances to live better. These are tricky things to work on, but with our data and expertise in AI, we’re in a great position to help brands figure these things out.




Will Clive
Chief People Officer • Pluralsight


A technology workforce development organization, Pluralsight helps thousands of teams upskill and transform at scale.


What is a key product, strategy or plan you’ve put in place to transform your business, or position you for the future and why?

Today’s job landscape in tech is challenging for organizations looking to retain top tech talent. To solve this challenge, Pluralsight is focused on being creators rather than consumers of talent.  For us, this means looking inward and investing in upskilling, reskilling and advancing our technology workforce. 

By investing in upskilling and workforce development, we are ultimately augmenting the knowledge, skills, and competencies of our people all while creating tech talent pipelines from within that will enable us to have the skills we need today and the skills we’ll need in the future, and remain competitive.


How is that strategy paying off for you now? 

As part of our skills development strategy, we created the Pluralsight at Pluralsight academies for all team members to skill up using our own Pluralsight Skills platform. 

For example, our DevOps Academy was an initiative to take non-tech employees with limited technical experience to conversational literacy in DevOps, and employees from a software engineering role to an entry-level DevOps role. Through this initiative, several software engineers entered much-needed DevOps engineer roles, and we experienced a certification exam pass rate of 89 percent, with nearly half the participants having little to no technical background.

We also ran our Cloud Happy Campaign, a three-month program that encouraged our employees to complete cloud courses and achieve certification. We created study groups so our people could collaborate with each other: it included study guides, weekly reminders, and “Cloud Captains,” or mentors, to answer questions. As a result, we saw a 95 percent adoption and completion rate; 98 percent passed their certification exam on the first attempt; and 62 percent applied what they learned immediately.

We truly believe that in order to build better products and deliver software more quickly — just like our customers seek to do — we have to build the talent we need to fill growing roles, and at the same time gain valuable insights into how we can improve our products for our customers.


What’s the most important lesson you’ve learned recently, and how do you hope to apply it to your business moving forward?

One important lesson I’ve learned through our investment in workforce development is that creating a continuous learning culture across an organization is all about facilitating learning to happen in the flow of life. It’s about behaviors and a mindset that comes from the top down. For example, our Cloud Happy Campaign was driven by our executives; our CEO and myself, for example, participated and got certified along with our team members.

At an organizational level, the culture depends on leaders being clear about what their ambitions are. At a more human level, a learning culture is about building trust with your people; they recognize you care about them enough to have an honest, open dialogue about what’s working well and what’s not.

At Pluralsight, our learning culture will continue to ensure an ongoing two-way dialogue where teams are supported, challenged and coached for optimal performance. To turn our learning culture into a tangible concept, we want all parties to understand the benefit that an investment in learning will bring.




Lisa Shim
Customer Executive • Point B


Point B is a global consulting firm solving complex business challenges through industry expertise and technological solutions. 


What is a key strategy, product, or plan you’ve put in place to transform your business, and why?

We have recently launched a new Retail Health practice, which is focused on helping our customers deliver healthcare in innovative, consumer-centric ways to achieve better health outcomes. We’ve brought together our greatest thinking in retail, healthcare and technology to bring our best, most forward-thinking insights to this disruptive intersection.

We’re leaning into this strategy because when it comes to improving health and wellness, we believe it’s critical to keep the consumer at the center. We recognize that we have the opportunity to improve health equity and outcomes for everybody, but especially for those who have historically been underserved in our communities.


 How is that strategy paying off for you now? 

We’re doing some incredibly innovative and impactful work with our customers, and in turn, it’s helping them move the needle on creating better health outcomes for their consumers and patients. Whether it’s helping one of our retail customers transform their pharmacy inventory system to better compete in the marketplace, or helping one of our healthcare customers adopt more retail practices in their approach to patient interactions — we’re focused on making healthcare more accessible for everybody.

This is also paying off for us (and our customers) because it’s in such close alignment with our brand and our values. The work we’re doing is creating and expanding ecosystems to include best practices from historically siloed industries and use leading-edge technology in new and different ways. It’s some of the best work we’ve ever done. And it’s allowing us to realize positive outcomes that improve our communities. We’re taking on some of the greatest challenges facing our world — like systemic health inequity — and making a sustainable impact. 


 What’s the most important lesson you’ve learned recently, and how do you hope to apply it to your business moving forward?

The most important lesson we’ve learned recently is that things change quickly! As our customers compete and find better strategies to win in the marketplace, they are innovating rapidly with how to leverage technology and digital experiences to meet evolving consumer expectations. The role technology is going to play in building consumer loyalty is only going to get more complex and critical. Our customers know that the importance of building trust, especially when delivering healthcare services to patients, is fundamental. We are working with leading-edge technologies and strategies, but we are also always looking to partner with others and grow our expertise to maintain that edge.




Elena Keush
AVP Operations & Chief of Staff Development • RingCentral


RingCentral offers cloud-based communication and collaboration products and services for businesses. 


What is a key strategy, product, or plan you’ve put in place to transform your business, and why?

At RingCentral, innovation is at the core and heart of everything we do. As a leader in cloud communications, there are many opportunities to provide insights and improve the user experience for customers with artificial intelligence. This strategy and technological focus has inspired how we operate, the features we launch and how we help people unlock powerful insights within their own communications data. 

In 2022, we launched Advanced Meeting Insights, an AI-based set of features focusing on meeting summaries and capturing key insights. This led to a richer, deeper product enhancement, which launched in March of 2023, called RingSense. RingSense is an AI-powered conversation intelligence solution that makes sense of all of your recorded interactions and unpacks each conversations’ goals and key concepts, enabling follow-ups that drive productivity within sales and revenue organizations. 

There are over 100 billion business calls made in the US alone every year, which are untapped for unstructured conversation data and customer insights we can glean to make meaningful decisions. Call recordings or transcripts alone are not a scalable way to understand what happened, action all the insights and extract all the value from these conversations  — especially if you weren’t on the call to begin with. Many of us have access to manual notes in CRM databases. Our goal is to close the gap between extracting insights across conversations and human interactions or unstructured data.
RingSense is transforming our business because it is helping sales reps uncover hidden opportunities within a conversation, outlining concrete action plans and feedback that integrate directly with your CRM — so you can focus on selling, not data entry. 


How is that strategy paying off for you now?

RingSense and AI-powered technology applies conversational intelligence into sales interactions and is transforming the way revenue organizations operate. RevOps professionals can review deals right where the conversations are happening. They benefit from improved forecasts, reduced risk, and have better collaboration with sales. This is one example of how RingSense is paying off. We’re able to integrate complex and technologically advanced features into a product that powers communication in the most simple way. 

Through our focus on AI-powered development, RingCentral has found an opportunity to help businesses extract more value from their recorded phone and video calls. It’s a simple, scalable solution to capture and analyze all customer calls and meetings to create visibility, drive process and behavior changes, and deliver bottom-line impact.


What’s the most important lesson you’ve learned recently, and how do you hope to apply it to your business moving forward? 

As RingCentral has increased our AI-enabled and AI-powered offerings, it is creating a lot of exciting opportunities for our technical professionals to grow and expand their skill set. One of the most important things I have learned recently is that sometimes the best way to help people reach their full potential is through acceptance of all skill sets and talents. Through my years of experience and development, I’ve also learned to focus on agile product delivery, understanding and listening to customer feedback so we can create real solutions that make an impact. 

And don’t forget to have a little fun! Of course we work incredibly hard — that’s how we come up with industry-leading enhancements like RingSense. But remembering to take time to share a laugh with a co-worker and share a meal with work friends — these things foster innovation as well. We may be focusing on AI, but it’s important to remember that we’re still human.




Garima Sinha
Senior Director of Product • Roblox


Roblox is reimagining the way people come together through its global community and immersive 3D experiences. 


What is a key strategy, product, or plan you’ve put in place to transform your business, and why?

Roblox’s vision is to reimagine how people come together. A core part of that is how people communicate with each other. What does it mean to communicate with others and express yourself in 3D worlds? What does it mean to hang out with people you care about? It’s a multiyear vision and to get there, we are building new technologies that can fundamentally change how people come together and interact in immersive 3D environments. 


How is that strategy paying off for you now? 

It's changing how people use Roblox. Playing games was a predominant use case, but now, new technologies like chat with voice and spatial audio are enabling our users to express themselves better. More experiences are getting created on Roblox that rely on these new mediums. This leads to more immersive and dynamic experiences, which is driving greater engagement on Roblox. 


What’s the most important lesson you’ve learned recently, and how do you hope to apply it to your business moving forward? 

Making communication and connection feel natural in a 3D environment is very special because it’s never been done before. A lot of new tech is being created to bring our vision to life, which requires us to rethink how we organizationally work together and collaborate. It’s no longer as simple as different teams building different pieces and connecting the dots. Each team has to understand the vision, understand where they can innovate, and how they can partner to bring it to life. This means we’re constantly thinking about how we can improve our organizational and collaboration model so our teams can work together as effectively as possible. 




Dan Jennings
Vice President, Pharmacy Renewal Engineering • Walgreens


Walgreens sells prescription and over-the-counter drugs, beauty and personal care items, fresh food and convenience products, and offers omni-channel access to consumer goods and services, pharmacy, and health and wellness services. 


What is a key product, strategy or plan you’ve put in place to transform your business or position you for the future and why?

It’s an exciting time to be at Walgreens. Walgreens is at an inflection point and is pivoting to become the leading partner in reimagining healthcare. Modern, technology-driven engineering approaches are at the center of that strategy and will be designed and delivered by the team members of Walgreens. We are building a world-class, innovative engineering organization.


How is that strategy paying off for you now?

In fiscal year 2022, Walgreens filled approximately 819.6 million prescriptions enabled by our technology. Were powered by the expertise, patient relationships and trust built over our 120+ years of serving the healthcare needs of people and communities.  


What’s the most important lesson you’ve learned recently, and how do you hope to apply it to your business moving forward?

Walgreens must balance the transformation of our technology and engineering culture, while continuing to deliver critical capabilities and meeting the existing obligations of our patients and customers. 

We are creating a technology culture that values individual autonomy with a bias toward action that fails fast and learns continuously. At Walgreens, technologists get to design technology that matters to the everyday lives of millions, while growing and learning. 


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