The Executive Gigger Model

Boston Globe - Brandon Ambrosino - 2016

For those who have spent time in a senior position, with an executive or C-suite level of responsibility and corresponding title, looking for their next opportunity might be a challenge.  Five years ago, the mantra was generally understood by execs looking that “it takes time to find your next position.” This historical baseline expectation shared by many now feels outdated in the instant economy.  It’s now 2018; technology and tools have reduced the time of searching and finding, working our network, and even soliciting a network referral is now down to seconds, and yet velocity of outcomes isn’t any “different.” The reality is that it still takes time. Hiring companies have also changed; the talent pool they pull from, the demographics they focus on, and other proprietary practices all reflect this. In the conflation of looking for a new role and the evolution of the changing employment dynamics, the cognitive dissonance that change is afoot means seekers need to adapt. The modern exec is left with an eroding list of choices: fight the gig economy or join it. This existential and purposeful awakening is real and here – and so is a new type of career.

No longer a mainstay of the contractor mindset, the freelance worker, the private contractor with a valid driver’s license, the remote python programmer, the database architect, blockchain expert, or bitcoin miner all now share common traits with each other; and it seems more and more with unemployed corporate executives.  In a recent survey, according to research firm Mavenlink, nearly 50% of business leaders today are seeking to retain on-demand workers specifically in management, senior executive and even C-suite.  This trend matches that of the modern exec who is seeking balance to contribute to learning, to mentoring, and to maintaining a comfortable standard of living. The impact of the gig economy is that a new wave of executive giggers are answering the call as a team of leaders. A tribe consisting of trusted peers they have worked with before, allying with investors and organically with startups to enter the evolution sooner and broader than before. If we look at the ride share as an allegory of the modern work force, these contemporary bands are offering their experience to solve the tech culture archetype of going fast, often at the expense of skipping steps. 

Since the explosion of the tech startup in the late 90’s, technical innovators and founders have endeavored to increase the chances of success, while assuring their investors (PE, VC, etc.) that they are making wise decisions. It is human nature to want to go faster than before, lean further over our skis, take risks. But every shortcut we take, every step we skip, comes with debt.  Entrepreneurs tell themselves that they will catch the kicked can, but debt comes with two consequences - it has to be repaid, and critical lessons are postponed.

In the last 20 years backers have learned the value of counter balancing founder’s risk-taking by installing hand-picked officers or advisors, often at the resistance of the founders. Both sides have seen the need to evolve the model.  More recently, investment firms have been adopting a different approach—employing mentors as house-call incubators.  These mentors, former executives, leaders, technologists, SME, and impresarios bring provenance and bona fides that are too impractical for a startup to onboard in early days.  There is a simple elegance to the fractional executive firm enhancing a portfolio with decades of knowledge, experience, wisdom, depth and breadth. Such a fractional firm of giggers, backstopped with personal resource networks that are supportive and effulgent, interested in knowledge and each other, unequivocally is the real unicorn. These are not returnship opportunities, they are relationship and a la carte. They allow startups, sophomores and rut-ridden companies a solution to debt and resilience at a salary cost that isn’t all bottom line. These experts know when to accelerate, when to scale and where the common pitfalls are, because they have seen and made mistakes that drive wisdom. 

The shared executive model is made possible through portfolio mentoring, with flat retainers of hours and not specific people or skills. What you need to crawl is different than to walk and run. Investors are rewarded with a knowledge that trusted experience is filling gaps and creating a safety net, while founders aren’t diluting key leadership positions, and they do not need to take on a CTO or CMO or CIO too soon. Equity isn’t in jeopardy, and companies can wean themselves off when the lessons and steps are achieved. The executive portfolio team may or may not place an employee at the company as part of the agreement, but as a transactional win-win, the possibilities are exciting.  Executive giggers are the force multipliers the industry has been cultivating, and now as free agents are ready to increase the chances of investment exit.