Roland Osborne

Principal

2021 - Current

Investing for 500's Global and Flagship Accelerator funds. Advising portfolio companies on fundraising, pitching, product, operations, and more.

Practice Director - Corporate Experimentation

2021 - 2021

Provided guidance for program design for other 500 programs that involved corporates running Proof of Concept and Pilot Programs. Worked with corporates and startups in the mobility, telecommunication, and finance spaces to identify opportunities and design time-bound experiments to identify partnerships with a high likelihood of success.

Entrepreneur In Residence | Innovation and Partnerships

2020 - 2021

Worked with corporates and startups in the mobility, telecommunication, and finance spaces to identify opportunities and design time-bound experiments to identify partnerships with a high likelihood of success.

Entrepreneur In Residence | General Motors Mobility Program Manager

2018 - 2020

Selected for investment and advised 3 cohorts of startups within 500's SF accelerator and helped them to successfully interface with General Motors to run proof of concepts. Advised these companies outside of their work with GM as their main point of contact within the accelerator program on pitching, product development, and strategy.

Entrepreneur In Residence

2018 - 2018

Advised local startups on marketing, metrics, product development, and how to build a successful work culture. Worked with UTEC Ventures to improve the quality of their accelerator program, increase opportunities for investment in their portfolio companies, and to facilitate the startup ecosystem in Peru.

Entrepreneur In Residence

2017 - 2017

Advised startups in Bosnia and Herzegovina in the areas of product development, marketing, and management. Devised changes to strategy at Networks.ba and Spark.ba for developing a successful startup ecosystem.

VP Product | Cofounder

2009 - 2016

Olark is the easiest way to add live chat to a website for lead generation, sales, and support. Co-founded and bootstrapped Olark from 0 to 10,000+ paying customers and ~40 employees. Together we pioneered the building of distributed teams and revolutionized the way customer support chat is done. My proudest accomplishment was bringing a culture of design and design thinking to Olark. I attended YCombinator in the summer of 2009 with Hab.la (which soon after became Olark). My ultimate focus was product and product team development but I lead our brand strategy as well for the the first 4 years.

Cofounder

2007 - 2009

User Experience Expert Product development, branding, marketing, graphic design, front-end development, and user experience.

VP / Web Developer

1998 - 2009

Developed usable and aesthetic technology solutions for clients. Portfolio: http://www.nethernet.com/#design Clients include: Name.com 9thx.com Fireworkspizza.com

Musician

2000 - 2005

Performed guitar and drums, composed, and recorded in a piano driven rock band with pianist Chris Merritt. Signed by Takeover Records with distribution on iTunes and Spotify.

Intern

2003 - 2003