The Expat Woman

Sydni Craig-Hart, 4th Generation Entrepreneur

Sydni Craig-Hart is CEO of Smart Simple Marketing and a 4th generation entrepreneur. Since 2006, her team, having worked with over 8,000 small business in 79 different industries, has been helping companies to drive engagement with sought-after, growing market segments. If you want to increase the value of existing-customer spend, recapture marketing investments, grow customer lifetime value or decrease attrition, be sure to connect with Sydni to discover how her team is doing this for companies like Facebook, Google, Instagram, LinkedIn and more.



Tell us a bit about yourself and your career path.

I’m the CEO and co-founder of Smart Simple Marketing, a digital content marketing agency based in Emeryville, CA. My husband and I launched our company in 2006 to help small business owners attract more clients and increase their revenue. We are still committed to that goal. In addition to serving small business owners, since 2013, we have been working with enterprise brands to build and market products that serve the small business community.

To date, we’ve worked with over 8,000 small businesses in 79 industries. Companies like Google, Facebook, LinkedIn, Instagram, Verizon, and others seek our expertise to help them gain market share, deepen engagement, and increase loyalty with small, minority-owned, and women-owned businesses.

I’m a 4th-generation entrepreneur, so owning a business was never a foreign concept for me. However, it wasn’t a goal either. I worked in corporate for 11 years, in financial services, before deciding to start my own company. I’m not someone who left my job because I hated corporate. I loved the jobs I had. I worked with incredible leaders, and I was well cared for by the companies I worked for.

Then, however, for a variety of reasons, my husband and I decided to move back to California (I’m a Bay Area native). While making that decision, I realized I would have to leave my perfect job, which happened to be in private equity fundraising. At that point, I decided I had taken my corporate journey as far as I wanted, and we started our company.


What was it like growing up in a family of entrepreneurs, and how has it played a role in who you are today?

My great-grandfather was the first African American real-estate investor in Los Angeles County in the 1950s. My grandparents had multiple businesses throughout their lifetimes, and my grandmother was the first black woman to be inducted into the Pasadena Chamber of Commerce. Most of my grandmother’s siblings had their own businesses. My dad started a tax business not long before I was born. Later, when I was in elementary school, my mom started a daycare in our home. As such, while I was growing up, discussions about starting, running, and growing a business were happening around me all the time.

I worked in my dad’s business when I was young, helping him sort receipts. As I grew up, I helped him with more advanced bookkeeping tasks. During the summers, I would work at my grandmother’s daycare. Thus, I saw first-hand how to take an idea from concept to launch. I learned how to get customers, serve and keep them, encourage referrals, and grow a business. I learned the value of hard work and how to navigate the inevitable challenges that come with being an entrepreneur.

Those experiences left a deep impression on me and have shaped my mindset as a business owner. I’ve developed a profound appreciation for the legacy my family has created and the impact their work has had on our family and the local community. Reflecting on their example pushes me to do my best work to support other small businesses and open doors for others, just as doors were opened for me.


Why did you become a member of The Expat Woman Club, and what do you like most about being a member?

I love meeting people, hearing their stories, and learning from them. I also love sharing resources and helping others. So, I’m always on the lookout for fun, interesting events to attend. The time I spend at The Expat Woman events is always time well spent. So, I was excited to see Nyna launch an online community where we could connect between events and deepen our relationships. I appreciate how hard the team works to keep us connected and reminds us of ways we can support each other.


What have been some of your biggest challenges and hurdles as an entrepreneur in the SF Bay Area?

Having a business in the San Francisco Bay Area is not for the faint of heart. It’s a very competitive market; trends unfold at the speed of light, and the cost of living is high. That said, incredible, inspiring opportunities are right at your fingertips, and you have priceless opportunities to learn from incredibly smart people. I’ve found that keeping the right mindset makes all the difference for how quickly and easily you meet your goals. It’s not always easy, but staying focused on what I’m good at and solving problems for my clients has kept me from feeling overwhelmed or discouraged. Having great mentors and a squad of cheerleaders helps a lot, too!


What is the one accomplishment you are most proud of achieving?

My husband and I have been married for more than 17 years. We’ve run a business together for over 13 years. The thing I am most proud of is how our relationship as a couple and as business partners has grown and flourished. We’ve made plenty of mistakes along the way, but we’ve learned how to work together and support and empower each other to do our best work. I am so happy and grateful that our marriage and business continue to thrive.


What is the one piece of advice you would like to share with entrepreneurs who are trying to drive engagement and deepen loyalty with their target audience?

Invest in getting to know your audience by talking to them regularly or inviting them to your office. Have conversations with a variety of people in your target audience and discover how your products and services fit into their lives. Pay close attention to:

  • What prompts them to look for what you sell
  • What problems they want to solve
  • How they think about your type of business

Discover their language and use it to connect in a relatable way. Think past the product or service you sell and focus on the impact you want to have on the customer, at which point you become an advocate for your audience and a trusted advisor to whom they will remain loyal.


What is your personal mantra?

“Always ask. The worst the person can say is no. More often than not, you’ll get a yes!”


How can The Expat Woman network support your endeavors, or how would you like to support our network?

I would love to support women who are looking to turn their experience and expertise into their own business venture. When you’re trying to figure out where to start, it’s invaluable to connect with someone who’s been in your shoes and can help you sort through your ideas.

I am a seasoned speaker and often deliver talks related to product marketing, UXR, multichannel marketing, and B2SMB marketing. I’m often invited to team off-sites, all-hands meetings, and other strategic gatherings to provide authentic insight on these topics. If you are a product manager, looking for a fresh perspective on how to engage your audience and drive sales, let’s chat! I’m happy to share “what’s working now” based on the results we are creating for our enterprise clients.


Connect with Sydni

Website:, Email:

Personal Handles: Facebook:, LinkedIn:, Twitter:, Instagram:

Company Handles: Facebook:, LinkedIn:, Twitter:, Instagram:


Nyna is the Founder and CEO of The Expat Woman, a global platform focused on connecting, supporting and empowering women who have moved abroad or plan to relocate. She is also a LinkedIn coach, consultant, trainer and speaker. LinkedIn played a huge role in my professional journey abroad, helping me build a network of powerful expat women and allies.

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