Skip to main content
Dionnie Headley - The tax guru - All Woman - Jamaica Observer
All Woman

Dionnie Headley - The tax guru


A tax advisor at Coopers & Lybrand (now PricewaterhouseCoopers) could not make it to work one day, so an intern at the company was asked to fill in for him. The intern, Dionnie Headley, was not even planning to go into the field when she finished university — she had merely taken the internship to gain work experience while she pursued a degree in human resource management.

But she always had a knack for simplifying complex matters to her friends, so when she was asked to educate a client about his taxes on behalf of her absentee colleague, she stood up to the challenge. Today, as the managing director of the Sygnus Tax advisory team, founder of the TaxTech Institute, and an adjunct lecturer in the master of science in taxation programme at The University of the West Indies, Headley is happy that she accidentally stumbled upon her true calling of being a tax educator.

“Apparently, I did so well that they said to me, 'Why don't you do this?' and I thought it was a good match, because this was really like counselling people about their tax situation, which complemented what I was studying in HR. I always loved the math side of things anyway, so it was a good combination,” she told All Woman last week.

At the time Headley was living and studying at Temple University in Pennsylvania, after having moved from Arlene Gardens in St Andrew, Jamaica, when she was 20 years old. Within a few months of her impromptu stint as a tax advisor, she became a full-time employee at PricewaterhouseCoopers (PwC) in the International Tax Services Group, where she delved head first into the world of international treaties and taxes in different territories across the globe. She did that for almost five years.

“And then I decided that I wanted to go on the corporate side. I moved to Atlanta, because of course, I was trying to run away from the cold anyway,” she laughed. “There I was in the corporate part of the business, and I worked with really large companies, and got into the other side of taxation, which I fell in love with even more.”

Headley was drawn to the complexity and diversity of issues which she found in taxation, and the constant new challenges kept her on her toes and wanting more. But she was yearning to come back home. Not only did the small-island girl dread the cold weather abroad, but she missed her homeland terribly.

“I think we have a wonderful country, and I think we can't look to others to fix it — it has to be us,” she said solemnly. “Everybody who knew me while I lived in the US knew that I was Jamaican. I wore it proudly, even in times when other people didn't want to wear it. And so, combined with the cold weather, and my passion for Jamaica, I always knew I was going to move back.”

In 2007 she returned home.

“That year as I was getting ready to come home for my annual visit, I decided to call PwC Jamaica and ask them if they had any available positions. As it turned out, they did,” she recalled.

She stayed at PwC for three years, during which time she became engrossed in Jamaican taxation, until family matters called her back to the US, where she went reluctantly.

She returned in 2012, after landing a job at Scotiabank Jamaica shortly after a friend asked her to fly down to present at a seminar.

“They had an opening, and what happened was that my bio was on the back of the flyer. So the head of Scotia at the time saw my bio, and asked my friend, 'Who is this person? This would be the ideal candidate', she said, marvelling at how well things fell into place when she decided to stay in Jamaica.

Headley's entrepreneurial spirit was awakened while she was at ScotiaBank, after she saw that there was a need for tax education locally.

“When I came back to Jamaica, one of my challenges was finding taxation classes to attend. There was no masters in taxation programme at UWI at that point, and I wanted to come and learn Jamaican taxation so I could be a specialist like I was in the US, but there was simply nowhere to go and get classes in Jamaica,” she bemoaned.

But Headley, who had considered being a teacher from her days at Pembroke Hall High School, when she would reteach lessons to her classmates for them to better understand, recognised that this gap in tax education was an opportunity for her to fulfil her childhood dream.

She founded the TaxTech Institute to develop and expand tax education in Jamaica, and to encourage and enhance specialisation in taxation. The institute frequently held one-day tax technical workshops aimed at broadening and enriching finance professionals with tax knowledge to enhance the practical application of tax laws in their job roles. She did this while maintaining her position as senior manager of tax & capital management at Scotiabank Jamaica.

While at Scotia she met two men who planned to start a business.

“I met Ike Johnson and Jason Morris, and we just jokingly talked about forming a company,” she shared. “Mostly, it came out of a particular project we worked on, and they said to me one day, 'You know, Dionnie, with the knowledge that you have about taxation, you should be doing your own tax business'.”

So when the men founded Sygnus Group, which also provides solutions in the lines of investment banking and investment management, it was only natural that they added tax advisory to the roster and made Headley the managing director.

As managing director, Headley is privileged to work with a six-member all-woman team — a job which she says is as challenging as it is rewarding.

“One of the things I learned in my career, having been in an area that was mostly men, is that managing men is different from managing women. Because, generally speaking, I think women are more communicative. And so they want to understand what's going on, and they want to be a part of leadership in a way, because of the fact that women like to be in the know,” she noted. “So coming from our PwC, and mostly working with men, to be honest, for me it was a big change in mindset in dealing with women, to know that I needed to be more communicative with them. And so our team is very tight, in that everybody is part of the strategic direction of the business.”

In addition to educating businesses about taxes at Sygnus, Headley occasionally lectures at The UWI's master of science in taxation degree programme. She was also recently asked to lead a taxation subcommittee at the Jamaica Chamber of Commerce. She also has a book in the making, which she will use to educate more people on taxation principles and policies.

“I always say that I can make lots of money if I want, if I want. In fact, if I wanted to make more money, I would have stayed in the US. But more importantly for me, I want to make an impact. And so for me, that means sharing the knowledge that I have gained over the years,” she said.

At just over 50 years of age, Headley hopes to retire early, but before she does, she insists on making an indelible mark in the field of taxes in Jamaica. She is excited by the new challenges which come up in her line of work.

“I like to be challenged; I don't know what it is to be bored. If I'm teaching, I'm in a good space, and if I'm learning I'm also in a good space. And as far as here, what keeps me going is the team, and you know, through rough times or challenges I think that the team that we have here at Sygnus as a whole, and then specifically in tax, is the kind of team that you know you want to stay in, because you want to make this thing really excellent,” she smiled.

Headley confessed to being quite the dancer at a house party (as that is how the music lover gets in some exercise) and a poet when the inspiration strikes, but enjoys most of all to spend time with her nieces and nephews when they come to visit.

Her personal and professional goals are one and the same — to be impactful to her nation by educating people about taxes.

“In any way that I can, I want to be influencing people's understanding of this discipline,” she underscored. “I think it will be helpful in their financial understanding of economics, and ultimately, of Jamaica. So I aim to be involved in different initiatives and projects and knowledge-based projects, which are geared to doing just that.”



1. We welcome reader comments on the top stories of the day. Some comments may be republished on the website or in the newspaper · your email addresses will not be published.

2. Please understand that comments are moderated and it is not always possible to publish all that have been submitted. We will, however, try to publish comments that are representative of all received.

3. We ask that comments are civil and free of libellous or hateful material. Also please stick to the topic under discussion.

4. Please do not write in block capitals since this makes your comment hard to read.

5. Please don't use the comments to advertise. However, our advertising department can be more than accommodating if emailed:

6. If readers wish to report offensive comments, suggest a correction or share a story then please email:

7. Lastly, read our Terms and Conditions and Privacy Policy

comments powered by Disqus