Digitally Transformative Leadership in a New Era of Work 

Sam Bright, Upwork Chief Product and Experience Officer

Much like so many other aspects of our life, the pandemic dramatically changed the way businesses operate. While digital transformation was already a major priority, the pandemic accelerated initiatives and pushed many companies over the tipping point. Suddenly, people’s personal and work lives moved online en masse, and organizations needed to adjust to keep up. 

Two years later, the world has adapted with remarkable speed. This new era has shown that digital transformation is not only crucial for businesses and organizations to survive—it’s revolutionizing how they operate, scale, invest and innovate for the long haul. In short, without it, they simply can’t thrive. 

But the transformation isn’t without its challenges. We’ve reached another turning point, thanks to the wave of workers who have left their jobs in the last year, a trend known as the Great Resignation. People are quitting in record numbers and a Upwork’s 2021 Future Workforce Report, a representative survey of 1,000 U.S. hiring managers, shows that the largest increase in freelancer demand was in the web, mobile and software development category, with a whopping 80 percent of hiring managers increasing their use of freelancers in this category since the pandemic began. The report showed the demand for highly skilled talent in the tech category is expected to continue, with nearly two-thirds of hiring managers planning to increase their use of tech freelancers over the next year. The demand for talent in these skilled roles, like cloud engineers, app developers, IT and network pros along with AI experts, is only going to become more acute because of digital transformation needs. 

As organizations continue to build, embrace and deploy new technologies and systems, they are grappling with continued talent shortages and finding themselves increasingly desperate to add the skills their teams need while avoiding roadblocks that slow down critical initiatives. Over the next year, it will become crucial for organizations to review and modernize their long-term management and talent strategies to fill gaps, strengthen their teams and drive transformation. 

With these pressures come opportunities. Leaders are willing to let go of generations-old beliefs around work and are waking up to the reality that they can no longer find the talent they need through traditional means. It’s an opportunity for a global work marketplace to empower both the professionals ready to innovate their careers and the businesses ready to innovate their work. 

Hybrid, distributed, flexible work models are the future and will drive a major competitive edge for companies looking to digitally transform. Take PGA of America, for example. A 100+ year old nonprofit institution championed digital innovation in 2021 by leveraging independent talent on Upwork to both extend skilled capabilities and boost team productivity. When their team of engineers came up with a new idea, they engaged specialized independent talent to quickly and cost-efficiently test a proof of concept. This approach enabled the team to introduce a new digital platform to better serve PGA customers and stakeholders, completing projects three times faster, saving an average of 50 per cent in costs, and accelerating projects to start within three days versus weeks.

Organizations that lag behind this trend will risk losing the opportunity to find high-performing professionals who are ready to make a difference and empower their teams to think bigger while working smarter. To future-proof, they must commit to a digital-first strategy that taps into a workforce optimized for flexibility, speed and agility. 

To do this successfully, they need a north star, a guiding vision. It’s important for organizations and their leaders to invest the time to create a shared vision and understanding between executive champions early on, while constantly bringing teams along in the journey. They must be clear with their assumptions for resource allocation assigned to new work models or digital initiatives and transparent about the potential challenges to attracting and retaining the talent required for successful execution. 

Finally, companies must also maintain empathy and give teams permission and support to experiment with and embrace these new ways of working. Leaders should encourage intellectual curiosity and approach digital transformation with an entrepreneurial mindset. Doing so while building a hybrid team of full-time employees coupled with independent talent can allow employees to focus on their core work while being exposed to fresh perspectives and expertise. 

If there’s anything the last two years have taught us, it’s that digital transformation cannot be ignored, delayed or deprioritized. It should live at the center of a company versus the periphery — it has to be core to culture, talent strategy and an ongoing driving force of the “disrupt or be disrupted” mantra. In today’s world, transformation is not a choice, but an imperative.