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Howard O'Brien has a solid background in sales and marketing. Howard began their career as an Account Specialist at VXI PH in 2013, where they provided call center and BPO services. Howard then joined iLeads Marketing Solutions in 2015 as a Sales And Marketing Specialist, catering to lead generation and B2B marketing services. In 2019, O'Brien became a Sales Manager at Leads Global Solutions, a leader in Lead Management Solutions, where they helped transform clients' goals into opportunities. Howard then moved to HexaDeals in 2022 as the Head Of Sales, providing efficient sales and marketing support to help companies reach their target audiences. Currently, O'Brien is the Head of Marketing at Callbox Inc, a position they have held since 2023.

Howard O'Brien attended Central Oregon Community College from 2008 to 2012, where they obtained a Bachelor of Science (BS) degree in Business/Commerce, General. Howard then went on to pursue a Master of Business Administration (MBA) degree from the University of California, Davis - Graduate School of Management, which they completed in 2021. Howard's field of study during their MBA program was General Sales, Merchandising, and Related Marketing Operations.

In addition to their formal education, Howard O'Brien has obtained several certifications. In September 2019, they became a Certified Sales Professional (CSP) through HubSpot. Howard also acquired a Sales Management certification in June 2020 from the same institution. Moreover, in February 2018, Howard earned the Accredited Business Communicator (ABC) certification from IABC (International Association of Business Communicators).