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Customer Success

Jesse Osborne: Onboarding the Gig Economy

In this interview, our host, Jessica Ly sits down with Jesse Osborne, Senior Director at Tipalti, to discuss how his company is providing a financial platform to gig employees in the workforce. He also talks about his leadership style and the importance of career planning.


Highlights of the Interview

The Gig Economy
A gig economy is a free market system in which temporary positions are common and organizations contract with independent workers for short-term engagements. Examples of gig employees in the workforce could include freelancers, independent contractors, project-based workers and temporary or part-time hires.

Situational Leadership
The situational theory of leadership refers to those leaders who adopt different leadership styles according to the situation and the development level of their team members. It is an effective way of leadership because it adapts to the team’s needs and sets a beneficial balance for the whole organization.

The Importance of Career Planning
A solid career plan is essential in that it can provide a roadmap for your future. This, in turn, helps you make informed choices about your current job situation as well as future career moves. A broader career plan is also important when it comes to helping you stay inspired.


Tipalti is the sole global payables automation solution that consolidates AP and payment management into one cloud platform. It simplifies supplier payments by addressing supplier onboarding, tax compliance, invoice processing, and payment reconciliation. With access to various payment methods and currencies, Tipalti ensures seamless communication of payment status and provides comprehensive reporting capabilities that help streamline financial operations.


Software Development


San Mateo, California

Jesse Osborne, Senior Director, Inside Sales, Tipalti