What is the top challenge facing small businesses in the coming year?

Frank Fiorille: The tightening of the labor market is having an impact on the rate of hiring at small businesses across the United States. Knowing the competition for talent is increasing, business owners should focus on how they can set their company apart in the crowded field of prospective employers. A comprehensive benefits package that includes traditional benefits like healthcare and retirement, as well as ancillary benefits like parking and gym memberships, can go a long way. Ongoing engagement and real-time skills development through a web-based learning management system can also be key to retention.

Michael R. Keane: Owning a small business today is significantly different than it was 25 years ago. Life has become more complex, which means more risks for a business owner. Data breaches, importing and exporting goods through online markets, leasing equipment, changing regulatory environments and using independent contractors are just a few examples of newer exposures that small businesses have that require unique expertise beyond basic insurance coverage.

Kirk Simpson: Cash flow will continue to dominate as a universal concern for entrepreneurs and small business owners. All the hustle in the world isn’t enough if your business closes because the money just isn’t in the bank when you need it. Of all small businesses that fail, 71 percent will cite poor financial management as the reason. I’ve been a small business owner, and I know that entrepreneurs would rather do just about anything other than bookkeeping, but it really is the key to better financial health.

Philip McHugh: The challenge that’s always present for small businesses is having time and resources, as owners need to serve as the head of marketing, finance, operations, sales, etc. Having to constantly manage and stay on top of all of these variables while continuing to grow your business is very complex. This is and will remain the number one challenge for any small business from now until eternity.

Chris DeMeo: Every small business is unique and faces its own set of challenges, but there are parallels across industries, one of them being talent. Finding and retaining top talent can be a challenge. Employees are the lifeblood of a small business, so managing them successfully is key. Step one is seeking out people who embody your business’ philosophy and mission, and then managing the workflow successfully. Businesses – both small and large – are embracing a collaborative approach to management to accomplish this.  

What is your company doing to support small businesses?

FF: Paychex makes it simple for businesses of all sizes to pay and manage their employees. With four decades of experience and over 650,000 clients, we relieve the complexities of payroll, benefits, HR and insurance administration so our clients can focus on what matters most: building their businesses. Through our unique combination of industry leading technology and personal service, we work with clients the way they want — online via their mobile device, over the phone or in-person.

MK: We understand that no day is the same for a small business owner and that flexibility is important. We continue to invest in insurance solutions to keep up with evolving risks small businesses face and align digital solutions for enhanced customer service. Working with leading independent insurance agents, we offer our small business clients insurance expertise, counsel and essential protection so they may focus more of their energies on their businesses. We also offer valuable complimentary and discounted services for business owners, such as background checks, worker safety training and business continuity planning.

KS: At Wave, we know that with entrepreneurs and small businesses, it’s the owner of the business who does the hands-on management of the finances, but that most entrepreneurs don’t have any training in how to do that financial work. We’re committed to providing integrated, truly easy-to-use software and services to make the money side of your business succeed. Wave also provides financial services like payment processing to make sure you get money in your pocket quickly for better cash flow and direct-deposit payroll built right into the software.

PM: We’re incredibly proud to have nearly 800,000 small- and medium-sized merchants as customers of ours in the United States. We provide simple, competitive and effective ways to take payments from their customers by providing best-in-class customer service and innovative technology solutions to make their lives simpler. We continue to roll out new, advanced point-of-sale offerings so our merchants can accept payments easier, plus we offer a variety of capabilities tailored to their specific business needs in order to allow them to solely focus on sales and growing their business while we handle more and more of their back-end needs.

CD: The core of Staples’ business is to provide companies of all sizes with the products, services and expertise they need to keep running smoothly, so they can focus on their larger goals and ideas.

Small business owners often have to wear many hats: office manager, accountant, marketer, recruiter etc. Whether shopping online or in-store our products and services support with these day-to-day needs so that the business can focus on their core business, whatever that may be.

  • Procurement through subscription services save time: For example, small businesses can auto-restock every 30 days when they need toner, paper etc.

  • Staples’ Print and Marketing services help small businesses with marketing needs to gain and retain customers, from business cards and signs, to direct mail and promotional products.

  • Beyond core office products, software and furniture, Staples also offers associate expertise and services (e.g., tech support).

What is one technology trend small businesses should be embracing going into 2019?  

CD: With the rise of remote working, there is an increasing shift to a mobile first environment. Small businesses should ensure their technology supports this type of mobility from apps to book conference rooms to various office messenger apps etc. Back in the office, conference rooms or other gathering spaces should be wired to support a variety of uses that can include video conferencing and presentation display, accessible from laptop or phone.

Small businesses note the ability to find capital and manage that incoming capital as their biggest challenge. What advice would you give them?

CD: Venture Capital/Investment firms often have very little to no time so small businesses need to ensure they have an excellent elevator pitch. Have a budget that you are able to backup and know your working capital cycle. Outside of the actual pitch, everyone on the team, not just the owner should always be networking with local VC and investment firms.

Small business owners are often tied up with so many different responsibilities that take time away from their core competencies. What aspects of their business do you recommend them outsourcing, and what aspects do you think they should keep in-house?

CD: Small business owners should focus on aspects of the business that impact how their brand is represented. Administrative work (e.g., payroll and billing) that don’t touch customers should be outsourced.

What’s a recent trend you believe will continue to impact small businesses into the new year?

CD: Talent retention will continue to impact small businesses in 2019 as the needs of the employees continue to evolve with the growing multigenerational workforces and the rise of the “work anywhere” trend. As the line between work and life continues to blur, small businesses must embrace the best ways to engage employees and keep them productive and happy!  The key is for employers to be willing to adjust and to adopt new technology that supports the changing work environment.