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8 Tips From a Serial Entrepreneur on Hiring, Growth, and Navigating Change

Illustration of SMB advice from a serial entrepreneur
Real-world advice for SMB owners and beyond — from hiring to scalability. [Getty | Nuthawut Somsuk]

Serial entrepreneur Stella Garber shares her experience in leading a small team, hiring top talent, and approaching exit strategies.

Look, it’s the wild west out there these days, and having inside advice on what works is gold. Running a business, let alone hiring, growing your brand, and finding and keeping customers, may be the most challenging thing for an entrepreneur yet. 

Small and medium-sized business (SMB) owners — looking for advice as you navigate a limited budget, growing pains, or find new business? We sat down with Stella Garber, Co-founder and CEO of Hoop, and previous Head of Marketing at Trello. She is a serial entrepreneur who chatted with us about her experience leading a small team, hiring top talent, approaching exit strategies, and navigating big change among many other big things.

Stella Garber, Co-founder and CEO of Hoop, and previous Head of Marketing at Trello

Here are the top questions answered: 

1. What were some early growth challenges?
2. What advice would you give small marketing teams executing on a limited budget?
3. How did you manage to keep up with so much change, and motivate your team to do the same?
4. What’s the biggest threat in scaling a business?
5. As a serial entrepreneur, what motivates you to turn your ideas into actual businesses?
6. What is your approach to an exit strategy?
7. What have you learned about hiring top talent?
8. What advice would you give fellow small business leaders or entrepreneurs who hope to achieve high growth?

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1. What were some early growth challenges?

When I joined Trello, the company was a small group, made up mostly of developers and designers. As the first marketer, I had a lot to prove to folks who believed that if a product was good enough, people would flock to it. While there is definitely some truth to that, as a marketing professional, I know that’s only true to a certain point.

Having worked in tech startups previously, I knew what I had to do to make everyone believe in the power of great marketing — I had to show it in action. 

One of the first campaigns I ran was a big press moment highlighting a user growth milestone for Trello, complete with email, content, and social components. After we saw the reaction from the media, users, and the market, our user growth trajectory skyrocketed. Suddenly, everyone could see the power of marketing and was ready to support my vision.

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2. What advice would you give small marketing teams executing on a limited budget?

It’s very easy to spread yourself too thin when you’re a startup or small business. You want to do everything all at once and can get blinded by the shiny, sexy, new things. I always encourage startups to experiment and figure out which channels are the most effective for them. Then, they should have extreme focus on those channels with an emphasis on consistency. 

For example, I encourage startups to focus on building email lists of interested potential users and customers before they launch. A lot of companies launch and then start to think about marketing. But if it’s launch day and you don’t have an audience, you’ve missed an opportunity to make a business impact. 

Consistency is key in reaching any type of goal, and in marketing, doing something each day — whether it’s writing a blog post, focusing on social distribution, or finalizing messaging — is vital to building marketing muscle.

Budget always comes up as an issue for small teams, but it’s never been an issue for me. A limited budget means you have to be scrappy and creative — a characteristic all small marketing teams should have. 

Larger companies with big marketing budgets often can’t execute as quickly as small teams and are further removed from their customers. Smaller teams should use this competitive advantage to shape their strategies and play to their strengths. Instead of lamenting a lack of budget, think about what customers truly care about and create meaningful content or use product marketing to scale.

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3. How did you manage to keep up with so much change, and motivate your team to do the same? 

If you ask my team, they’ll tell you one of my favorite expressions is that “the only constant in life is change.” Being a person who thrives on ambiguity is important if you want to be part of a startup. Luckily, that’s me. I love the challenges that come with things breaking and figuring out how to fix them as a startup grows — that’s a sign that things are going well. 

I see change as an opportunity to optimize, improve, and grow. This is true both for the business, as well as an individual’s career. And this is how I framed the change that was occurring at the time to my growing team. Growth gives people opportunities they may not have had otherwise, so ambitious individuals will thrive in a growth-driven environment because they are constantly challenged.

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4. What’s the biggest threat in scaling a business?

The biggest threat in scaling a business comes from getting too comfortable pursuing a winning strategy without constantly taking stock of the competitive climate. Often, when startups find product market fit, they get tunnel vision executing on what has previously worked in a rapidly changing environment. 

It’s important to constantly stay on your toes and deliver on what makes your company or product unique while understanding how customers’ needs may change over time.

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5. As a “serial entrepreneur” what motivates you to turn your ideas into actual businesses?

I see a problem in the market as an opportunity to impact change. My family emigrated to the United States from the Soviet Union when I was a child, and my parents have always emphasized the opportunities available to me that they never had. This gives me the motivation to act, rather than sit on ideas until they’re perfect. 

I understood from starting businesses young that many people are afraid of failure, or think they aren’t ready to start a business until they accomplish some goal or get so many years of experience. Entrepreneurs know that you’re never truly ready, and that the only way to succeed is to start, learn, and iterate. 

I always used to think: What’s the worst that could happen? If you plan ahead, take mitigated risks, and solve problems smartly, the downside isn’t so bad. It’s certainly not as bad as what my family experienced in the Soviet Union — anti-Semitism, corruption, fear for their lives. That puts things into perspective for me.

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6. What is your approach to an exit strategy?

When you’re writing a business plan or thinking about launching a business, you have to consider potential exit strategies. It’s part of the planning and qualifying process. After that, however, it’s important to buckle down and focus on building a product and delivering significant value to customers.

One thing I’ve learned over the years is that it’s easy for founders to get funding when they don’t need it, and it’s significantly easier to sell a company if you don’t need to. If you’re put in a position where you have to fundraise, or you have to pursue an acquisition, you tilt the power away from yourself and into the hands of the unknown market. Most likely, the outcome won’t be in your favor. That’s why it’s most important to do something you’re passionate about and can see yourself doing for a very long time, then consider exit opportunities as they arise.

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7. Over your time as a CEO and a founder, you’ve hired many people. What have you learned about hiring top talent?

Here are the top three things I’ve learned about hiring talent:

  1. Have a skills-based interview: Make sure candidates do some sort of mini project or assignment that they’d do on the job. Use that to drive the interview process so you focus on the concrete work and not on more ambiguous things like “culture fit.”
  2. Involve multiple people: Design a hiring process where multiple people look for different aspects. For example, one person may look at a person’s writing ability when hiring for a marketing role, whereas another person may look at verbal communication, creativity, or values.
  3. Hire people for their potential: I’m a big fan of hiring ambitious people who have a spark and desire to grow. I like to hire for the skills they will have, rather than the skills they may have today. This is important for a startup because what a person does this quarter or year may be totally different based on the company’s needs in a year. You want to hire people who are flexible and have previously shown success in changing environments.

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8. What advice would you give fellow small business leaders or entrepreneurs who hope to achieve high growth?

Don’t chase after trends. I see too many entrepreneurs get blinded by one company’s success in a market and create a derivative product or service to take advantage of that success and make a quick buck instead of choosing something they find personally interesting or exciting.

Think Groupon clones and the “on-demand” trend from a few years back: there were one or two winners and thousands of losers. Instead, it’s important to chase a problem or opportunity that entrepreneurs feel passionate about fixing for the next ten years. 

Use that framework to qualify a business idea to make sure entrepreneurs start a business for the right reason, and not just to piggyback on someone else’s success. Once they’ve chosen an idea and have started building a product, I’d encourage them to have a few key values that drive the business. 

For example, Trello had product and brand tenets from day one that we continue to reference and pursue. Sticking to these values keeps the team focused in a changing environment, and gives the team something to rally around. This shared vision ensures startups won’t get distracted by advice or adjacent opportunities.

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Take this SMB advice and get ahead of change 

One last tip from all of us here at Salesforce. Make the tools work for you. Generative artificial intelligence (AI) is here to help you shave the minutes off minute tasks, so why not integrate it? As the #1 AM CRM, we are built on data, so take these tips and make them work for you through automation and AI. 

And, Salesforce Starter Suite is here to help you find more customers, win their business, and keep them happy so you can grow faster than ever.

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