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 futurists, Tiffini 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 owner, Tiffini’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’ needs. For instance, the working from home / childcare scenario. We’ve become very good at finding that balance. 

From a business standpoint, because our major revenue was from shows and tours, we really had to pivot and find new revenue resources. The bands are pivoting, too—we’re all in it together. 

My role has changed completely, and it’s not just number-crunching. Now I’m working with a smaller team on getting funding, seeing what grants and programs are out there, and keeping those connections with the industry. The industry is so small, but we’ve been really good about sharing resources with other companies like ours.  

We’re international/national, so we have no local clientele. But we felt compelled to support local businesses – we printed t-shirts for all of the local companies and they were able to sell them at a profit. We also got into branding masks from each artist and sales are skyrocketing. 

 How have you worked to incorporate technology into your company’s finance department?  

TM: We recently moved from Magento to Shopify for its user-friendly analytics. That’s made us more unique and willing to try new things. I’m working on marketing and learning to understand that feedback may not necessarily result in sales. There may be a lot of likes, but it doesn’t really result in any revenue.  

 With these analytics and that insight, I’m learning what works and what doesn’t work and where to spend the marketing budget. With COVID-19, I thought I’d hoard my company’s cash but actually the opposite is true—I’m spending it in different avenues and in new ways to bring the company revenue.  

 What future opportunities are you most excited about? 

TM: I’m excited to make this wholesale and retail market work for our business. Financially, I’m pleased to see it’s more profitable than it’s been in the past. Once the tours are able to open, I think it’s really going to set us up. We’re going to have that base that we didn’t have before on top of the tours.