The digital age has radically altered the employment landscape. The once standard nine-to-five routine is going the way of the dinosaur; if you’re a dog lover, a social media aficionado, or just really good at putting together Ikea furniture, there’s a side hustle for you.

But what if you’ve spent the last 30 years building your career? What if you, for example, recently left a lofty leadership position as an enterprise CTO, and aren’t hungry for a new full-time gig? Or maybe you’re considering retirement, but know you have more to offer. Is there a side hustle for proven leaders? What would the “gig economy” look like for gig executives?

We have a hunch. Read on. 

Independence in the Digital Age

Autonomy is key when it comes to the digital economy. Greater numbers of employees are contributing from every conceivable location – what does “out of office” mean when your company is spread throughout the world? There are now hundreds of companies with no central office. 

InVision, for example, has nearly 1,000 employees who work remotely from around the globe. Even office-bound employees have the ability to take off for two weeks in the Bahamas, spending their mornings on a laptop and their evenings on the beach. 

According to McKinsey, “Nearly 162 million people in Europe and the United States – or 20% to 30% of the working-age population – engage in some form of independent work.” And this isn’t just about the Uber drivers and AirBNB hosts of the world.

At Emissary, we believe the gig economy ought to work for highly accomplished professionals too. We’re contributing to a new trend as full-time position-holders and recent retirees jump into the independent-work lifestyle. We call it the Executive Gig Economy.

The Executive Gig Economy

In the Executive Gig Economy your currency is your experience. While an apartment-owner may rent out their space as an asset, a member of the Executive Gig Economy offers insight based on knowledge gained through leadership. 

At Emissary, we’re building a new kind of network to foster this trend. Our community of current and former executives offer their guidance to technology sales teams seeking to demystify the enterprise sales process. As we’ve become familiar with these executives, we’ve noticed a few patterns in this rapidly growing population of executive gig-seekers. 

Just as AirBNB renters fall into recognizable categories (single room rentals, residence rentals, or investment property rentals), our Emissaries have created three new categories within the growing Executive Gig Economy: Post-Career, New-Career, and Mid-Career.

The New Retirement

Retirement has changed. When we think of classic idea of retirement we might still picture beaches and golf courses, but for many newly-departed industry leaders there’s a lot more to it than that.

Through work on our platform, “post-career” Emissaries are moving from leading an organization to leading the transformation of the marketplace. This happens through mentorship of younger companies seeking to gain from these leaders’ wealth of experience, and through guidance provided to established companies who’ve reached a brick wall in their relationships with current business partners. Our Emissaries are uniquely positioned for this transformational work. 

Emissaries like Jim Fortner, former CIO/CTO of Procter & Gamble, have found that there is a path into post-career life that doesn’t involve an abrupt shift from 10-12 hour work days to a sudden halt in commitments. “I really like helping companies and teams win. It gives me the opportunity of moving across industries. It’s been fun.”, Jim said to us. “You get to come in and out of different business situations and provide coaching based on your point of view.”

Jim is able to maintain his old business contacts gained through 30+ years of experience, but is now networking at a different level: as a visionary and guide to the next generation of innovators. He is free to build his brand, while working as much as he chooses. It’s time for a new retirement paradigm, and Jim is among the forward-thinkers who are defining it.


The Second Act

What if a seasoned executive is ready for something new, but isn’t prepared to retire? Maybe self-employment has always intrigued them, and they’re wondering how to leverage the deep breadth of experience they possess while considering their next step. A cohort of our Emissaries are building companies of their own so that they can transition into post-professional life on their terms.

Emissaries like Thomas Martin, a former CIO and VP of Application Transformation at GE, whose company BigCoSmallCo is redefining the relationship between small tech firms who are seeking to increase the reach of their products and large enterprises who could benefit from those technologies. Thomas has found a new niche for himself as a partner for both tech disruptors and large, well-established organizations.

In Thomas’ words, “Disruption today is happening by these smaller startups that don’t have the resources or weight that enterprises have. The chasm between the two entities is large, and BigCo.SmallCo. bridges that gap to help each side understand the challenge enterprises face when working with startups in order to bring real value to the enterprise.”

Thomas’ work with Emissary feeds directly into his own consulting practice, and offers him unlimited opportunity to build new relationships.

Ginnie Roeglin, who recently finished a 27-year tenure at retail giant, Costco, as the SVP of eCommerce, is another great example. She is now able to apply her vision to her own business practices as CEO of marketing firm, Influence Marketing. This transition allows for a newfound freedom while giving back to the marketplace, as Ginnie mentors industry up-and-comers through platforms like Emissary.

“After 27 years, I decided it was time for me to begin a new chapter rather than to actually retire. As I build my Loyalty Marketing Company, I also find my work with Emissary to be intellectually stimulating. I am connecting with many talented people, and staying current with fast-moving technology and marketing in the retail and eCommerce sectors, while at the same time helping others succeed in their efforts to sell to Costco and other multi-channel retailers.”

The Full-Timer as Contractor

There is equal opportunity in this new environment for mid-career professionals who have no interest in winding down, or setting off on their own. There are two clear benefits for this group: to become more familiar with a growing number of technology vendors, and to effect positive change in the marketplace, accomplishing both while maintaining a high-profile career that’s on the rise. In the Executive Gig Economy, even a high-stakes leader with skin in the game can find a rewarding gig or two on the side.

Eric Toda, former global head of social and content at AirBNB, puts it this way: “I’ve been introduced to so many companies doing things that I’ve never heard of [through Emissary], so I get exposure to organizations that are on the front lines of new vendor relationships…If you can educate the head of sales to leverage the right network and the right stakeholders to get into [a large enterprise], they’ll stand a better chance. These companies who are using Emissary will make much better decisions based on insight.”

Eric is a perfect example of give and take within the gig marketplace. He benefits by growing his network of potential vendors as a current digital marketing leader while making a few bucks in the process as he cuts his consulting teeth, and is, in turn, offering his insight to help “…empower these teams to be and do better” (his words).

Where We Go from Here

It’s clear that the momentum of this burgeoning new economy is only quickening, and that technology is the centerpiece. CNBC, while investigating these shifts, found that “Over the past 20 years, the number of gig economy workers…has increased by about 27 percent more than payroll employees.” McKinsey predicts that “By 2025 [digital platforms] could add $2.7 trillion to global GDP…”. By 2030, it’s conceivable that there will be more self-employed workers in the US and abroad than individuals who are traditionally employed.

As more and more industry leaders participate in the Executive Gig Economy, minds with the vision and influence to transform work as we know it will bolster this trend. New platforms and initiatives will spring up: benefits packages for contractors, debates around the self-employment tax, sole-proprietor unions, and others. It’s an employment wild west.

At Emissary we’re proud to be leading the charge in offering unprecedented opportunities to industry leaders around the world. The executives we invite to work with us have the chance to not only reshape the enterprise sales landscape but also to redefine work itself as technology opens up new vistas for independence and connectivity.

We believe in a future that is powered by both technology and relationships – that knowledge is as valuable a commodity as convenience – and that everyone has the right to a piece of the gig action. We’ll be proud to be part of the sea change ahead.