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Cummings was born in Dunedin, New Zealand, and raised in Australia. He developed an early interest in broadcasting and began volunteering at a local community radio station at the age of 13.

Cummings began his career at 101FM Logan City, gaining early experience in community radio. He later worked with 96five Brisbane and Nova 106.9 as a panel operator and on-air presenter, where he hosted weekend and late-night programs.

At age 17, he became the youngest full-time commercial announcer in Australia after joining 91.9 Sea FM on the Sunshine Coast.{{cite web |date=5 January 2016 |title=Top New Talent to Watch in 2016 |url=https://radiotoday.com.au/top-new-talent-to-watch-in-2016/ |website=Radio Today}}

He was recognised in 2016 by *Radio Today Australia* as one of the country’s top new radio talents.

In 2017, Cummings moved to the UAE to join 104.8 Channel 4 FM in Dubai. He co-hosted the national breakfast show Wake Up UAE before being given his own afternoon show. The program became widely popular, and Cummings established himself as a household name in English-language radio across the UAE.

He later joined Virgin Radio 104.4, where he currently hosts The Night Show with Jacob Cummings. The program is considered the most interactive English-language evening show in the country and is one of the most listened-to English radio shows in the region.{{cite web |title=Jacob Cummings |url=https://www.virginradiodubai.com/onair/the-night-show-jacob/ |access-date=16 May 2025 |website=Virgin Radio Dubai}}

Cummings has also hosted high-profile events in the UAE, including:

• Jennifer Lopez’s Dubai concert.
• The Globe Soccer Awards red carpet.
• The All Saints Spring Collection launch at Expo 2020 Dubai.

In 2023, Cummings worked in the U.S. radio industry in Los Angeles for one year, gaining international broadcasting experience and exposure.

Cummings currently hosts Wake Up with Jacob on 91.4 Energy Radio 1, a station owned by Aramco. The show is broadcast from his studio in Dubai each morning to audiences across Saudi Arabia. It is the most listened-to English-language morning show in the country.{{cite web |title=Energy Radio 1 |url=https://energyradio.sa |access-date=16 May 2025 |website=Energy Radio Saudi Arabia}}

He has also hosted major public events in the Kingdom, including:

• The World Firefighting Challenge in Dammam.
• The Al Sharqiya International Marathon.
• Multiple corporate, cultural, and entertainment events.

Cummings holds the Guinness World Record for the fastest time to collect five balls in water on a waterbed, with a time of 1 minute and 38.82 seconds. The record was achieved at Yas Waterworld in Abu Dhabi during a Guinness World Records Live event on 26 November 2021.{{cite web |title=Fastest time to collect 5 balls on a waterbed (lilo) |url=https://www.guinnessworldrecords.com/world-records/674722-fastest-time-to-collect-5-balls-on-a-waterbed-lilo |access-date=16 May 2025 |website=Guinness World Records}}{{cite press release |title=Yas Waterworld Guests Break 6 Guinness World Records |url=https://www.prnewswire.com/in/news-releases/yas-waterworld-guests-break-6-guinness-world-records-tm--872240429.html |access-date=16 May 2025 |website=PR Newswire}}

Cummings is known for his high-energy presentation style and relatability across a broad international audience. His career spans multiple countries and includes both on-air broadcasting and live event hosting.

• [https://www.virginradiodubai.com Virgin Radio Dubai]
• [https://energyradio.sa Energy Radio 1]
• [https://www.guinnessworldrecords.com Guinness World Records]