Finance Futurists: Why 25 years later, Tiffini Masessa is still eager to learn and grow as a CFO

The Finance Futurists are an elite group of leaders who embrace constant evolution as a necessity in the ever-changing world of finance.  

More than number-crunchers, these leaders represent a new era for finance—one defined by a shift from pure analytical expertise to emotional intelligence and strong communication skills as well. Here, we spotlight one of this year’s futuristsTiffini Masessa, CFO Forward Merch, and what she believes the future holds for the finance function. 

For nearly a quarter century, Tiffini Masessa has cultivated her impressive finance experience at Forward Merch, a New Hampshire-based business that creates, produces, and sells official merchandise for a number of music’s most renowned acts, including David Bowie, AC/DC, Pink Floyd, and Phish to name a few. 

Now serving as Forward Merch’s CFO and ownerTiffini’s worked to increase and optimize budgets while incorporating key technologies to improve workflows, payment processes, and analytical capabilities. Beyond those more typical finance functions, Tiffini also works closely with Forward Merch’s marketing team to ensure customers receive the most well-rounded support possible. 

We recently chatted with Tiffini about her extensive finance and merchandising experience, how her role as a CFO evolved in light of COVID, and why female empowerment and corporate social responsibility are two defining factors informing her current approach as CFO. 

How did you start your career in finance, and what about it appealed to you? 

Tiffini Masessa: I started with Forward Merch in 1996 after working at one of the fleet banks that turned into Bank of America. I was a business banker and got to know the president of Forward Merch at the time.  

Before interstate banking came along, bands and artists would come in with boatloads of cash. In music merchandising, we manufacture anything you buy at a concert. So, any time a tour came through, they’d drop off a lot of cash. Unless they had a bank account in every state, they had no place to process all of that cash.  

When I started with Forward Merch, I would go to venues and fill up a backpack with this cash and come home in the middle of the night. That was the start of my journey to becoming CFO at the company. 

What’s the initiative or accomplishment you’re most proud of throughout your career? 

TM: The empowerment of women in my business. A majority of our managers are women. I’m not taking credit for their abilities, but I feel really blessed that I work for a company that empowers women in leadership positions. That’s the most rewarding, personally.  

But professionally, it’s also super rewarding just to see our business grow. When I became an owner, the budget wasn’t really on track. Things were happening that I didn’t really approve of. I’m just really proud that we’ve gotten all of those finances in order and we’re on a trajectory for growth. 

Many industries struggled to maintain growth during the height of the COVID-19 pandemic.  How did you adapt to its economic impact?  

TM: Naturally, there’s a fine line – you have to be tough, but you also have to be responsive to your employees’

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