Millennial Business and Life Mastery - Barbados 001 | Page 6

Top 30 Millennial Bajan Entrepreneurs Under 30
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THE HR BOSS
Recently Jameela has taken a deep dive into the political
landscape in the area of political strategy in 2018. Her strat-
egy enabled her first political client to overthrow a 62 year
strong hold parish which was never held by the now ruling
Barbados Labour Party. At present she serves as a Board
Member of the Rural Development Commission and on the
special projects team established by the Government of Bar-
bados for the restructuring of specific Government entities.
Jameela’s mantra in life now is “ What doesn’t kill me,
better run!”
1.) Who is Jameela Hollingsworth in business (describe)
?
Jameela Hollingsworth
Bio: Jameela Hollingsworth is the owner of the HR Boss
a Caribbean millennial career consultancy with readership
in over 27 countries. The HR Boss was founded with the
mission of helping Caribbean millennials kick butt and take
names and be the Bosses they were destined to be. The Har-
vard trained Leadership communicator has travelled to three
Caribbean territories in 2017 delivering Career Seminars and
empowering Caribbean millennials to take charge of their ca-
reers. In 2017, The HR Boss expanded to Toronto, Canada
being the second location of the agency. In 2018, Jameela
was nominated to attend to the International Visitor’s Lead-
ership Program in Washington, DC in recognition of her con-
tribution to entrepreneurship in Barbados in her two years on
operation.
Jameela is a qualified HR practitioner with over 8 years’
experience in Jamaica, Barbados and St. Lucia. At present
she serves as the HR Business Partner for a regional group
of companies. The Barbadian native holds a Bachelor’s of
Science in Human Resources Management from the Uni-
versity of the West Indies, Mona Campus, Jamaica and a
Master’s in Business Administration from Edinburgh Napier
University, Scotland. Jameela is a certified recruiter & psy-
chometric assessor and has helped thousands of persons
take charge of their careers.
Millennial Business and Life Mastery Magazine
A: Wow. I am a 29 year old HR practitioner with over 8
years’ experience in the region. I am a professional trou-
blemaker, challenger of HR norms regionally, professional
speaker, community leader, political strategist and servant of
the people. I do not practice “human resources”, I serve the
most critical resource of the business (the people).
As an entrepreneur, my team and my clients would de-
scribe me as the real life Olivia Pope as I seek to exceed their
expectations and get the job done by any means necessary.
2.) What inspired you to first start the HR Boss?
A: I started The HR Boss in 2016 out of frustration. I at-
tended a HR Conference and someone made a statement to
me that summed up meant that I was too young to be seen
as an expert in the field and I basically had to stay in my lane
and wait on my turn to be promoted or to be paid “fairly”.
That was the main driving force that lead me to regis-
tering the business that very day. The name “The HR Boss”
came about in me venting on my way to CAIPO to register
the business; I was in the car reassuring myself that I was a
“Boss” at what I did (which was HR). It’s funny looking back
now but then I was determined to prove them wrong and
make a name for myself. Turning negativity into a motiva-
tion and eventually a positive outcome has always been my
strong point.
3.) What are some of the best lessons you have learned
about being an entrepreneur in Barbados?
A: Ask a question, there is someone who has been there
before you. By seeking help when I hit roadblocks I’ve met
an incredible group of businesswomen which I am now priv-
ileged to call my friends. There is this big misconception that
business owners are reluctant to share information but you
won’t know if you ask.
Don’t take no for an answer. Stay the course. If an oppor-
tunity does not work out for you with one client there will be
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