This CFO Says Bookkeeping Is Broken — So She’s Fixing It With Technology

Unless you’re a CFO or finance manager, it’s hard to fully appreciate the tediousness and time it takes to recruit and hire an effective bookkeeper for your business’ needs.

For longtime finance exec Natasha Goldstein, the struggle was a particularly frustrating one. During her time as the director of finance at a New York social enterprise, Goldstein spent a grueling six months searching for the right bookkeeper with the right skills to work alongside her. What she found was that, although she understood finance and accounting, she didn’t know how to select and manage a bookkeeper.

“I was asking a bookkeeper to generate financial statements and I didn’t know they couldn’t,” Goldstein says. “It’s kind of like if you’re looking to hire an engineer but you know nothing about engineering yourself, so you can’t identify the right type of engineer you need for the job. Companies don’t know how to identify the right bookkeeper for their needs.”

This disconnect stems from the reality that accounting is somewhat distant to the typical skills of a bookkeeper. Data entry is their main undertaking, not managing financials reports and budgets on a broader level. What companies need but rarely find is a healthy duo of both fields to leverage these separate skills in a productive manner.

Years after first experiencing this, Goldstein decided to tackle the challenge so other CFOs don’t have to. After only a few months of planning and bootstrapping funds, Goldstein and her co-founder launched their own tech-enabled outsourced bookkeeping and accounting service, The Accountkeepers.

For $1,000 per month, The Accountkeepers clients are granted a bookkeeper who does 70 percent of the work to manage billing, tax records, categorizing credit card transactions and expenses, regular financial statements and some payroll processes — the daily grind of keeping track of a company’s finances.

The other side of the service offers account managers who work to absorb the raw data the bookkeeper handles on a regular basis and translate it for executives in a way that’s conducive to better financial outcomes for the company as a whole. Essentially, they oversee the bookkeeper’s work on a broad level.

Goldstein believes the relationship and collaboration between these two fields is precisely the change the traditional finance management model needs today.

How frustration led to opportunity

Goldstein has already seen a positive response for her services. Companies connect with the challenge she’s solving, reminding her of the challenges she first experienced at her former role.

After a move from New York to North Carolina, along with a few career changes, Goldstein was reacquainted with the same demand she had faced years earlier when she heard members of the Triangle business community discussing their difficulties hiring a bookkeeper.

Following a stint working at an impact investing non-profit as managing director and CFO, she decided she wanted to do something more leadership-oriented. She left her finance job to start leading the expansion of NC IDEA SOAR, a mentorship program for North Carolina’s women entrepreneurs looking to raise early capital.

There, she learned that a third of the SOAR companies suffered bookkeeping challenges as well.

“I must have heard it from 30 people that it’s absolutely an issue,” she recalls. “So I saw this huge need and the entrepreneur in me couldn’t help myself.”

Her first step was to find a co-founder, a lesson she had learned early in her career when she started a social impact investment fund. Goldstein had to let that business go, partly because she had started the company alone and needed additional human resources to help run it.

It was clear to Goldstein that the same need would apply to her new company. She called an old friend, Chantal Sheehan, who also understood the challenge she intended to address from her own career experience.

Since the pair officially launched The Accountkeepers in September, they’ve signed on four clients and have many more in the pipeline. The Accountkeepers is targeting investor-funded medium to large companies. Though most companies are in North Carolina, Goldstein says the service certainly isn’t limited to companies in the state — she hopes to expand The Accountkeepers’ reach in the coming months.

Though the target market isn’t early startups, Goldstein routinely gets questions from startups for help on accounting topics. She’s able to help them in the additional role she’s taken on as a part-time Entrepreneur in Residence in Launch Chapel Hill, a startup incubator and co-working space for University of North Carolina students and Chapel Hill community members. Goldstein regularly fields inquiries asking for finance recommendations and advice from the program’s participants.

She says she wants to offer something to help startups figure this out. She’s looking to partner with startup incubators and organizations like HQ Raleigh, The Frontier at Research Triangle Park, American Underground and NC IDEA to give vetted startups some support with their accounting.

Harnessing new technology in an old-school field

Though The Accountkeepers’ mission serves to improve the financial operations within its client companies, Goldstein also has a separate but equally important goal to better the workforce climate for bookkeepers. The field has an increasingly high turnover rate, another reason why Goldstein believes the in-house bookkeeper model is ineffective — she says bookkeepers are undervalued by their employers and less likely to move up from their positions.

The Accountkeepers is challenging that status quo by offering its bookkeepers the chance to move into account management once they learn the necessary skills. Bookkeepers can also work remotely.

“The constraints of the regular workplace are not necessary,” she says. “I saw a need and also said we need to change the workplace. Flexible schedules work.”

The Accountkeepers emphasizes innovation as part of the package, employing the latest technologies influencing the financial industry. They do this by combining the best features of the best tools—like Bill.com and Expensify—to get their work done on a daily basis. The outsourced component to The Accountkeepers’ services strengthens this model.

“What I find is that once people are in-house, it’s not in their wheelhouse to learn the new technologies,” Goldstein says. “They don’t have the capacity for that.”

This provides an extra value-add for the demographic the Accountkeepers is aiming to serve. ”We’re making it our business to do that for clients.”

The act of harnessing technology to improve daily job performance is key to cultivating a productive workforce. And in doing so, Goldstein believes she can create an environment that proves the importance of outsourcing finance industry talent rather than keeping it limited to in-house monotony.


Shannon Cuthrell is a freelance journalist, published author and recent graduate of Appalachian State University. Aside from writing, she’s passionate about astronomy, avocados, cats and mass media trends.