The Great Resignation & The Future Of Work: Indiana (Indy) Gregg Of Wedo On How Employers and Employees Are Reworking Work Together

An Interview with Karen Mangia

SKILLSHARING. Industries will be more likely to share employees fractionally, making it possible for an individual to report to multiple companies, delivering skill-based expertise and splitting time between them.

When it comes to designing the future of work, one size fits none. Discovering success isn’t about a hybrid model or offering remote work options. Individuals and organizations are looking for more freedom. The freedom to choose the work model that makes the most sense. The freedom to choose their own values. And the freedom to pursue what matters most. We reached out to successful leaders and thought leaders across all industries to glean their insights and predictions about how to create a future that works.

As a part of our interview series called “How Employers and Employees are Reworking Work Together,” we had the pleasure to interview Indiana Gregg.

Indiana Gregg, CEO and Founder of Wedo.ai, the neobank social networking application that helps the independent economy save time, money and energy and run their business seamlessly online. She is a 5x tech founder, member of Forbes Technology Council, reality bender and team builder.

Thank you for making time to visit with us about the topic of our time. Our readers would like to get to know you a bit better. Can you please tell us about one or two life experiences that most shaped who you are today.

In 1993, I made the pivotal life-altering decision to move abroad, and by default out of my comfort zone.. I can say with absolute certainty I would not be the woman I am today had I not explored other countries outside of the US. I I encourage young people to step out of their comfort zones, explore the world, and take advantage of the new nomad visas that many countries are offering. Living in numerous countries has given me so much insight into cultures both on a macro and micro level.

While in my twenties, I took a leap onto an entrepreneurial path. I knew early-on that my vision and mission in life did not align with the cadence or style of a more traditional day job. The plan was always to be a founder, or help founders pursue meaningful technologies and products, which has consumed most of my professional career. Now it’s worth mentioning that I had a brief stint as a singer/songwriter, an exciting and insightful experience, which sparked my desire to evoke change in the music industry. All of these experiences, from world traveler to rockstar to entrepreneur, have led me to where I am today, on a mission to disrupt the future of ‘work’ as we know it.

Let’s zoom out. What do you predict will be the same about work, the workforce and the workplace 10–15 years from now? What do you predict will be different?

I predict very little will be the same 10–15 years from now. Automation and AI are changing the way we work. In 15 years, we will have droids fulfilling many of the jobs that are currently employed by humans. In 15 years, we will be holding in-person “holographic” meetings across the globe where the virtual impact will be much more interactive than AR/VR. The fractional and remote workforces will be fully mainstream. Talent pools will become fractional, and job sharing — a practice in which companies divide and distribute roles allowing employees to work for two or three companies rather than a traditional 40 hour work week for one employer — will be much more common. The global political system will have changed its position on work as well. More and more countries will adopt digital nomad visas and the freelance economy will be mainstream. There will still be bumps in the road and new legislation being developed to protect the gig worker, and the rules will change around taxes, insurance, and social security.

What advice would you offer to employers who want to future-proof their organizations?

Remain agile. Be prepared to hire talent abroad. Get a better understanding of what you can automate versus what requires a human in the loop, and plan for it. Invest in your people, especially in software and technological skills. Build a culture of flexibility and high-vis accountability. Invest more time in KPI and OKR planning. Build teams that work together seamlessly across departments. Invest in internal communications for your business. Create a plan for future revenue opportunities in case your business is in a sector that could become obsolete or fully automated.

What do you predict will be the biggest gaps between what employers are willing to offer and what employees expect as we move forward? And what strategies would you offer about how to reconcile those gaps?

We are already seeing resistance from employers on topics like flexi-work, four-day work weeks, and remote work in several industries. If they want to build a winning workforce, they need to get organized and embrace the change with a big hug. I believe employers are going to need to understand that the millennial generation and beyond are all about quality of life. They are concerned about the environment, they prioritize work culture and desire enough free time to experience life. Long gone are the days of brow-beating your team into working long hours and living to work rather than working to live. The era of profitability over everything else is slowly screeching to a halt. Employers need to be authentic and hire based on culture fit. This needs to be spelled out very clearly from the get-go. The young workforce has been penetrated by social media and requires more flexibility and autonomy, pushing employers to focus on OKRs rather than total hours worked. Putting in accountability and spending time developing culture-fit in the workforce will be crucial to mitigating employee churn and developing a healthy company culture.

We simultaneously joined a global experiment together last year called “Working From Home.” How will this experience influence the future of work?

Millions in the tech industry have been working from home for years, as have the vast majority of freelancers. So, for many of us, this was business as usual. The movement towards this phenomena was already a hockey stick for tech companies pre-Covid. Covid just accentuated the fluidity of businesses that had already embraced a remote workforce. These businesses observed how they could reduce overhead while creating a happier and more productive workforce by not forcing a commute. What we’ve seen since the lockdowns is more and more companies adopting a hybrid approach, keeping the human contact alive while allowing employee autonomy. This approach is likely to stick. For those companies whose leadership is based on a micro-management culture, they will continue to churn only to potentially die in the future.

We’ve all read the headlines about how the pandemic reshaped the workforce. What societal changes do you foresee as necessary to support a future of work that works for everyone?

Embrace change. Women are now a major influence in the workforce, it’s no longer a man’s world. This is indeed a good thing because the societal shift has improved diversity, and women solve problems from a different point of view. The workforce has become more diverse.

Secondly, we’re moving into a knowledge-based society. Automation, computerized systems, and software, as well as hardware and robotics, have improved the quality of life for humans in general. We are rapidly moving away from the traditions set forth in the 20th century.

Stand up for change. The types of legislation to protect the workforce and empower growth are at our fingertips. I encourage everyone to advocate for change in labor and workforce legislation in order to promote this rapid acceleration, encouraging freedom and flexibility. With such legislation, politicians and government agencies will have the ability to promote a more fluid approach to benefit the freelance and gig economies, as well as employment law.

What is your greatest source of optimism about the future of work?

I believe we will move into a society where we all fit into the hexagon. There are many positive trends towards a better world; it’s up to us to make the future happen and the time is now. I believe we’re building the infrastructure now in order to leave a legacy for a better tomorrow. More and more companies are opting to become B-corp companies with a focus on sustainability and diversity. Our economy is interwoven and although we still have borders on the map dividing countries, as humans we have never been more connected. Long live that connectivity.

Our collective mental health and wellbeing are now considered collateral as we consider the future of work. What innovative strategies do you see employers offering to help improve and optimize their employee’s mental health and wellbeing?

Employees need to feel connected while simultaneously maintaining ownership of their lane. For the out-of-the-office culture, this is imperative to drive efficiency. Connectivity means creating room for employee development and investing in your workforce through offsites, training, and other team-building experiences. Investing time and energy in company communication and developing leadership that resonates with their teams is fundamental. Empowering your workforce and creating great leaders not only from the top down but laterally from within is crucial in a hybrid or remote workforce. Gone are the days of the micro-manager. Human capital drives companies forward and investing in your workforce is the key to success in any business. There’s no substitute for a happy workforce.

It seems like there’s a new headline every day. ‘The Great Resignation’. ‘The Great Reconfiguration’. And now the ‘Great Reevaluation’. What are the most important messages leaders need to hear from these headlines? How do company cultures need to evolve?

Companies need to genuinely care about their employees. It’s time. If you want to lose money continually rehiring and have churn in your workforce, then stay stagnant and fail. Leadership needs to invest in coaching or change management. Continuing to do the same thing and failing shouldn’t be an option. We are letting go of the industrial revolution and moving into a knowledge-based society where the rules of work require this revamp. An employer should mainly care about setting reasonable targets and creating OKRs with their teams. Leaders need to take necessary measures to be flexible with work hours and promote healthy lifestyles for their teams. I believe Wedo will be a huge part of this global shift, empowering people to help more people through the future of work, so check us out!

Let’s get more specific. What are your “Top 5 Trends To Track In the Future of Work?”

1. PEOPLE & HR DRIVEN BY ANALYTICS. HR will be driven by data and OKRs will become more important in order to track performance rather than time spent. Goals will be set and tracked by individual performance as well as team performance and departmental objectives.
2. SKILLS EMPHASIS. Companies will invest more in upskilling, with the hope of reducing churn by bringing talent up the pipeline rather than hiring top down. Skills will be tracked in order to close up holes in expertise to better identify where new skills can be developed within teams rather than hiring people for a specific skill. As a result, roles may become more diverse and fractional in terms of time spent in specific lanes.
3. FLEXIBLE AND HYBRID. Due to enhanced data processes, people can expect their jobs to be more flexible. Work from home will be more of the norm with hybrid and flexible time on and offsite. Office square footage will shrink and be used primarily for small gatherings and administrative purposes.
4. SOFT SKILLS FOCUS. As more and more jobs are replaced by AI and automation, there will be a stronger need for soft skills and strategic knowledge-based thinking. Businesses will place more emphasis on company culture and communication within their workforces, encouraging people to develop a growth mindset in both their work and personal lives. Leadership and team relationship development will become increasingly more important.
5. SKILLSHARING. Industries will be more likely to share employees fractionally, making it possible for an individual to report to multiple companies, delivering skill-based expertise and splitting time between them.

I keep quotes on my desk and on scraps of paper to stay inspired. What’s your favorite “Life Lesson Quote”? And how has this quote shaped your perspective?

“Not all storms arrive to disrupt your life. Some storms come in order to clear a path for you.” I relate to this not only because it’s true, but I’ve had some of my greatest breaks and opportunities immediately following some of my biggest failures or let downs. The shift towards a more autonomous workforce may feel like a storm or challenge for some companies. Embrace it, the toothpaste is already out of the tube and you can’t put it back.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He, she, or they might just see this if we tag them.

Oh wow. I’d love to have breakfast with Oprah Winfrey. I’ve loved her since her early days in Chicago. As a midwesterner, watching her break glass ceilings has been a huge inspiration. I love Arianna Huffington and her perspective on the modern workforce and work/life harmony as well. I’d love to meet Reid Hoffman. His way of communicating with startups is inspiring. Oh, and I’d love to have lunch with Marc Andreesen and Ben Horowitz. They are simply epic. And I really love Will Smith, one of my current investors has a bet on how long it will take to get Will on our cap table. I can see him fitting in with our company vision hugely.

Our readers often like to continue the conversation with our featured interviewees. How can they best connect with you and stay current on what you’re discovering?

I post a lot of information about Wedo on my LinkedIn and do weekly video updates on our progress. I love sharing the cool new things our team is up to. You can follow our team members on our company page as well. Most of our team posts really insightful information, not only about the company, but about work-life balance. (We have an epic team at Wedo. I just LOVE this team). Readers can also follow Wedo.ai on Instagram, TikTok, Linkedin, and Twitter, or keep up with our company blogs at Wedo.ai. Download the app on IOS or Android and join our OG community of people who are amazing ambassadors for Wedo!

Thank you for sharing your insights and predictions. We appreciate the gift of your time and wish you continued success and good health.

It’s a pleasure to share anything I’ve learned that can help businesses succeed. Our mission with Wedo is to ‘help more people to help more people’ and we’re living that mission every minute of every hour. I’m grateful for this opportunity to share. So, thank you!

About The Interviewer: Karen Mangia is one of the most sought-after keynote speakers in the world, sharing her thought leadership with over 10,000 organizations during the course of her career. As Vice President of Customer and Market Insights at Salesforce, she helps individuals and organizations define, design and deliver the future. Discover her proven strategies to access your own success in her fourth book Success A Success From Anywhere and by connecting with her on LinkedIn and Twitter.