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This CEO Is Striving to Build the Best Workplace for Parents in the US

How Natasha Goldstein built The Accountkeepers with flexibility at its core

This CEO Is Striving to Build the Best Workplace for Parents in the US

Natasha Goldstein has worn many hats over the years—she’s been a chief financial officer, entrepreneur, mentor, investment banker, wife, and mom. With experiences as varied as hers, she was bound to end up with a stockpile of wisdom. The most important lessons she’s learned over the years? Run with a great idea if you have it, and never be afraid to ask for what you want.

Goldstein worked in finance for over a decade and ran into a common problem: finding the right bookkeeper to meet specific business needs was a near-impossible task. Knowing her peers were struggling with the same issue, her inner entrepreneur began scheming.

After a few months of planning and bootstrapping, Goldstein launched the tech-enabled outsourced bookkeeping and accounting service, The Accountkeepers, alongside her co-founder. One year later, and she’s not only filling a major void in the tech industry but also providing amazing benefits to her employees, who happen to be all women!

Goldstein built her startup completely on her own terms. Her tenacity and passion for a positive company culture is definitely something worth talking about. Read about her perspectives on women’s entrepreneurship, awesome working environments, and future plans here:

You’ve been involved with startups and entrepreneurship now from a number of different perspectives—working for a fund, spearheading a mentorship program for women entrepreneurs in North Carolina, and now leading your own company. Which of these roles has been your favorite, and what are some of the key takeaways or lessons you have to offer?

I have to say, running The Accountkeepers is my favorite by far. I love being able to craft the work environment I think we need more of in the US, particularly for working parents. The Accountkeepers offers everything I have always felt employers should offer, which is tremendous benefits, flexibility, and generosity.

My background has given me a lot of different perspectives. Before running the fundraising and financial end of an investment fund, I started my first company in 2010—LIFT Investments. Starting LIFT taught me about fundraising, mostly how incredibly hard it is and how you really need to have something outstanding to be successful.

At MCE Social Capital, I raised about $20M per year in capital and was also the fund's CFO. This was my second stint as a CFO. In those roles I learned how to run a business and how to manage people successfully. At the end of the day, my experiences have taught me that it's incredibly hard to start a successful company, incredibly hard to raise money, and incredibly rewarding when you do.

There’s a lot more awareness these days about the challenges women face both in the workplace and specifically in starting their own companies. Which trends concern you the most about female entrepreneurship, and which give you the most hope?

I could talk about a lot there, but I'm most troubled right now by the lack of flexibility afforded to dads! Until the workplace allows dads more flexibility to be the one to pick up a child at daycare by 6 p.m., or leave work to get a sick kid, it's going to be really hard for women to break away from being the "available" parent and do what it takes to start a company.

I started The Accountkeepers a year ago in October 2017, and my husband was able to pick up a lot of slack with our two kids. He has had to work really hard to get that level of flexibility at his workplace, and he is not the norm. Work environments expect women to "ask" for these accommodations, and they expect men not to.

What gives me hope? A ton! We are seeing a lot more flexibility in the workplace. We are seeing more focus on female entrepreneurship and how to support it. We are talking more about why so few women get funded, and getting to the root causes of that.

You had just recently gotten a new job and were mom to a little one when you began planning and bootstrapping funds for The Accountkeepers. We often try to wait for the “right time” to start new projects, but there never is a perfect time to start something—there will always be an excuse. How did you overcome hurdles and nix the excuses to start The Accountkeepers?

I had a 1-year-old and a 3-year-old when I started The Accountkeepers, and I honestly didn't understand fully what I was getting into! I really just couldn't help myself. I felt like the need in the market was clearly there, and I could build the exact type of company I think we need more of in the US. It's rare in life that you see a clear opportunity, know you can meet it, and know it will allow you to build something you will love and care about. It has been totally worth it.

What’s your work-life balance like now that you’re the CEO of a startup?

Honestly, it's great. The first six months were very hard with some long hours, but once we understood how to do what we're trying to do (provide tech-enabled outsourced bookkeeping), things have smoothed out. We have amazing staff, and would be nowhere without them.

I work hard for about eight hours a day, and stop at 5 p.m. I get my kids, have dinner with them, and usually go to bed pretty early. I try not to work much on weekends. We didn't raise money for The Accountkeepers, so not having investors to worry about has really alleviated a lot of stress. We are growing the business steadily each month and in a way that is manageable for everyone, including me.

Women are often viewed as abrasive when they are assertive at work. How do you view assertiveness in the workplace as a professional woman? What advice do you have for other women who want to be more assertive at work?

I have always been assertive, and it's never hurt me professionally. I think people confuse assertiveness with being rude. There's a big difference.

If you approach something with strong reasons and data, I find that goes a long way. I'm sure there have been people who haven't liked me for being assertive, but that's alright with me. At The Accountkeepers, we encourage our staff (who are 100% female) to speak up about anything that's not working. We have pivoted our business model several times, in fact, due to staff speaking out. I hope we are giving them a platform to exercise their assertiveness!

The Accountkeepers scores a 4.0 or above on 14 of 16 metrics on our site, and scores an exceptional 4.2 overall. Tell me about the benefits that Accountkeepers offers its employees.

We are striving to be the best place for working parents to work in the US, and that's largely about flexibility. Benefits include:

  • 75% of medical, dental, vision insurance

  • Life and disability insurance (LT and ST) paid

  • Unlimited vacation

  • Total flexibility—you can work any schedule so long as it works for your team and your clients

  • 18 weeks paid parental leave

  • 5% contribution to your 401k, no match required.

We have a staff member whose daughter plays water polo all over the country, and she travels all over the US to see her. She is an amazing employee, getting everything done exceptionally well. As long as there's internet, we can work!

Your frustration with a lacking, yet necessary category led to an amazing opportunity. What are your goals for The Accountkeepers in the next few years?

We have learned that in order to have happy staff and happy clients, we need to add clients slowly and carefully. We move our clients over to new systems and processes, and that requires time, education, and patience. We are going to grow steadily and hire employees steadily. We are creating space for our staff to stay on top of tech trends and what's going on in our space (which is ever evolving).

To learn more about The AccountKeepers, visit their website at

For more empowering stories of professional women making waves, check out InHerSight’s inspirational features on working women.

By Cara Hutto

Born and raised a Tar Heel, Cara is a culinary aficionado and zealous writer consumed by wanderlust. She's passionate about women's issues and interviewing inspirational women in her community.

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