SSGI Insight · Leadership Story
Proof of Work: How Andrew Decker Built Across Insurance, Operations and Emerging Technology
Andrew Decker's path runs through early internet entrepreneurship, large-scale operations, insurance agency management, a worker class action, public service and emerging technology. The common thread is learning by building.
An unconventional operating education
Andrew Decker began building businesses in the late 1990s, when launching a company online still meant learning much of the infrastructure as you went. One of those early ventures, Outside Element, became the first chapter in a career shaped less by a single industry than by a repeated operating pattern: understand the system, build the organization, and test the work in the real world.
Over the years, Andrew started and operated businesses across several fields. Each venture added a different kind of fluency — customer acquisition, systems, finance, people, technology, risk, and the discipline required to keep an organization moving when the conditions are imperfect.
That background matters at SSGI because employee benefits do not exist in isolation. They sit inside an employer's budget, workforce strategy, payroll, technology stack, service model, and long-term plan. Andrew approaches benefits as an operator who understands those connected pressures.
The strongest credential is work that can be examined, tested, and improved.
Learning what scale demands
At one stage of his career, Andrew led call-center operations serving banking and telecommunications clients, including an organization of roughly 1,000 people. At that size, good intentions are not enough. Performance depends on clear processes, measurable standards, accountable managers, usable technology, and an ability to see where work is breaking down.
Large operations also make the human cost of weak systems impossible to ignore. A confusing process is repeated hundreds of times. A missing handoff becomes a customer problem. A tool that saves a few minutes per interaction can return thousands of hours to the organization.
That experience continues to shape how Andrew thinks about benefits administration: automate repetitive work, make ownership visible, and keep a qualified person accountable for the decisions and exceptions technology cannot resolve alone.
Working inside demanding environments
Andrew's career included work at JPMorgan Chase and in Xerox Major Accounts. Those roles exposed him to large institutions where reliability, discretion, security requirements, and operational continuity were part of the everyday standard.
His Xerox work brought him into complex institutional environments across Maryland, Washington DC, and Virginia. The lesson was not simply how large organizations buy technology. It was how systems must perform when many people, departments, and controls depend on them at once.
That institutional perspective now sits beside SSGI's family-owned model. The aim is to give employers disciplined, enterprise-grade execution without losing direct access to the people responsible for the work.
From agency management to catastrophe-insurance training
Before leading SSGI, Andrew worked as an associate agent with State Farm and developed practical experience in insurance agency management. The work added a field-level understanding of how an agency coordinates sales, service, staffing, accountability, and customer trust.
Andrew also earned the Certified Insurance Representative (CIR) — National Association of Christian Catastrophe Insurance Adjusters, an insurance-related professional designation that added catastrophe-insurance training to his agency-management experience.
Together, those experiences gave Andrew a broad operating view of insurance: the product matters, but so do the systems, people, controls, and follow-through surrounding it.
From workplace accountability to public service
In 2011, Andrew served as the named plaintiff and class representative in a WARN Act case brought on behalf of former employees. Working with employment attorney Jack A. Raisner, he helped pursue a resolution for a certified class of 133 workers.
The case concluded in a $250,000 settlement. For Andrew, the experience reinforced a lasting principle: institutions should be accountable for decisions that affect people's livelihoods.
While the litigation was underway, Andrew filed a statement of candidacy for the U.S. House of Representatives on October 14, 2011, in New York's 28th Congressional District. He later stepped away from the race, but the experience extended the same focus on accountability from the workplace into public service.
Building for insurance today — and emerging systems tomorrow
Today, Andrew is President of Strategic Sequoia Group Inc. He runs SSGI Benefits operations and strategic direction, working with Laura Decker to combine experienced insurance guidance, responsive service, and modern technology inside a family-owned company.
The work includes improving the systems around enrollment, administration, communication, and renewal while keeping licensed people accountable for recommendations and decisions. SSGI's technology should reduce unnecessary work; it should not create distance between a client and the person responsible for helping.
Andrew is also founder and President of Circuit Labs, where he is developing patent-pending artificial-intelligence technology. His current research and building extend into AI, blockchain, cloud computing, coordination systems, and the future of work — subjects that also inform his published SSGI perspective on how technology may reshape healthcare and employee benefits.
Why demonstrated capability matters
Andrew places greater weight on self-directed learning, demonstrated capability, and work that can be tested than on credentials alone. That is not an argument against formal education. It is a standard for what should come after it: can the person understand the problem, build a responsible solution, explain the trade-offs, and improve the result?
Blockchain has become one of the environments where he studies that principle most closely. Public ledgers, inspectable code, and systems that must behave as designed put unusual pressure on vague claims. The work either holds up or it does not.
That same proof-of-work mindset shapes Andrew's leadership at SSGI: make ownership clear, measure what matters, improve the system, and remain accountable to the people who depend on it.
A career connected by operating discipline
Entrepreneurship, a 1,000-person operation, JPMorgan Chase, Xerox Major Accounts, State Farm, workplace advocacy, a congressional candidacy, SSGI Benefits, and Circuit Labs may look like separate chapters. The connecting idea is consistent: learn the system deeply enough to improve it, then accept responsibility for whether the improvement works.
That is the standard Andrew continues to bring to SSGI's operations, technology, and long-term direction.
About Andrew Decker
President of Strategic Sequoia Group Inc.
Andrew Decker runs SSGI Benefits operations and strategic direction and serves as President of Strategic Sequoia Group Inc. His work spans insurance, large-scale operations, artificial intelligence, blockchain, cloud computing, and the future of work.
Meet Andrew and the SSGI leadership team