From Farm to Tech CEO: Heather Udo's Journey to Building a 500 Million-SKU SaaS Empire

In this insightful episode of The Nathan Newberry Show, Heather Udo, founder and CEO of Shoppable, shares her remarkable journey from growing up on a Wisconsin farm to building a thriving SaaS business with a product catalog of 500 million SKUs. With 13 years as a software CEO and now coaching first-time founders, Heather offers valuable lessons on entrepreneurship, team building, and navigating the complex world of tech startups.

Early Foundations: From Farm Chores to Entrepreneurial Mindset

Heather's entrepreneurial journey began in an unexpected place—a hobby farm in Wisconsin, where she was one of eight children. This upbringing instilled two critical traits that would serve her well in her future business endeavors: independence and work ethic.

"We were all very independent and kind of raised to have that independence in a way to kind of go after what we wanted."

Her parents provided a weekly allowance of just 25 cents—an amount so small it couldn't buy anything meaningful. But rather than simply increasing her allowance, her parents presented a valuable lesson in entrepreneurship:

"Our parents would say, 'Well, you've got to find a way to make up the difference.' That's kind of what we were taught, and they encouraged us to find other ways."

This early training in self-reliance led Heather to explore entrepreneurial opportunities, including leveraging the internet and eBay at an early age to generate income. These formative experiences, combined with her physically demanding farm chores—building fences, baling hay, and shoveling manure—created a foundation of resilience and problem-solving skills.

When it came time for college, Heather made a pivotal decision to leave Wisconsin for San Francisco at age 18. This move wasn't just about escaping the cold Midwestern winters; it placed her directly in the epicenter of the tech revolution. During her first year in San Francisco, a fortuitous entrepreneurship class taught by a Microsoft professional introduced her to the world of venture capital and Silicon Valley, igniting her passion for technology.

The Power of Entry-Level Experience: Learning Through Doing

One of Heather's most transformative experiences came during an internship at Monster.com (once the LinkedIn of its day), where she demonstrated remarkable initiative by reaching out to an entrepreneur who had just sold his company to Monster.

"I emailed the entrepreneur who had just sold his company to Monster and asked if I could speak with him because I said, 'I want to start a company one day. Will you give me five minutes of your time?'"

Though the email likely "sat on her desktop for a long time" as she overthought every word and sentence structure, her courage to send it yielded life-changing results. Not only did the entrepreneur respond, but he was so impressed by their meeting that he invited her to join him for dinner with two VPs to discuss his next startup. After signing an NDA and thoroughly studying his pitch deck, Heather came prepared with substantial value and opinions, leading to a job offer before she had even graduated college.

This experience taught Heather one of her most emphasized lessons for aspiring entrepreneurs—the immense value of entry-level positions:

"It's so important to say yes to everything and it's so important to be the first one in and to stay late and to take on everything you can and just soak up as much information as you can because those are the years that are so valuable for learning."

Working as the first non-executive employee at that startup provided Heather with an invaluable education. She went from PowerPoint to exit over four years, gaining experience in marketing research, operations, sales, business development, and account management. As the company grew, she built teams around these functions and leveled up her responsibilities.

"I got paid to get my MBA with that experience that allowed me to then in turn go and start Shoppable."

Heather cautions against the modern tendency to rush career progression, noting how she sometimes encounters job candidates with just one year of marketing experience who expect to become CMOs. The foundation built in those early roles, particularly when you have fewer responsibilities and dependencies in your life, creates the building blocks for future success.

Building Resilient Teams: Solutions Over Blame

Another crucial lesson from Heather's early startup experience was the critical importance of having the right people around the table—especially when facing significant challenges. She recalls several crises that seemed business-ending at the time, including a weekend when they returned to discover massive fraud in their lead generation system.

"I thought, 'Oh my God, we just sent all this fraud to our biggest customers. There's no way we can come back from this.' And of course, we did."

This experience taught her two vital principles that have guided her leadership approach ever since:

1. With the right team, any problem is solvable. Having people who can work together effectively makes seemingly insurmountable challenges manageable.
2. Focus on solutions, not blame. Heather emphasizes the importance of not wasting time pointing fingers:

"You can't waste time pointing fingers and say who forgot to do this or who created this issue or who didn't do XYZ. You can't waste your time focusing on that. You have to focus on the solutions."

This solution-oriented approach has become such a core part of her leadership style that her current team at Shoppable is often surprised by her calm demeanor during crises:

"Sometimes when there's a quote-unquote 'big issue,' my team is like, 'How are you so calm right now?' I'm like, 'I've seen it all at this point.'"

Scaling Shoppable: Strategic Decisions for Growth

When it came to building her own company, Heather applied these accumulated lessons while navigating new challenges. Shoppable began as a B2C business before pivoting to SaaS about a year in—a strategic shift that positioned the company for greater growth.

After initially bootstrapping, Heather completed a rolling seed round of about $2 million to accelerate growth. One of her key strategies was leveraging an advisory board to open doors to enterprise clients:

"We created an advisory board and stacked it with advisers that had existing relationships with people who already had those relationships. They set up the meetings for us, and then they came to the meetings with me. We co-pitched, and that helped us get several of our customers."

Today, Shoppable integrates with thousands of different merchants including major partners like Walmart, Sephora, Macy's, Walgreens, and Best Buy, managing a product catalog of 500 million SKUs. This massive data infrastructure presents unique engineering challenges, as the entire catalog must be refreshed multiple times daily—a feat that even much larger companies have struggled to achieve:

"There's a large social media site that we were speaking to maybe two years ago... they had maybe 10 million or 100 million SKUs at that time, and they said they hadn't been able to update it even once a day. Our team was significantly smaller than theirs, and they're like, 'How are you guys doing this?'"

Essential Advice for Aspiring Entrepreneurs

Drawing from her extensive experience as both a founder and now a coach for first-time entrepreneurs, Heather offers several key principles for startup success:

1. Don't Reinvent the Wheel

Particularly for tech businesses, Heather advises entrepreneurs to be strategic about what they build versus what they license or partner on:

"Sometimes people, especially technologists, get over-ambitious with what they want to build on their own, and they think because they can build it, that they should build it."

2. Keep the Customer at the Center

Customer-centricity should drive all decisions, from product development to service delivery.

3. Profit Cures Everything

Heather emphasizes the importance of having a clear path to profitability from the beginning—something too many early-stage entrepreneurs neglect:

"Too many entrepreneurs don't have an idea for revenue when they first get started. People get so excited about the idea that they sometimes don't even think about how will I make money and can I make money."

4. Identify Whether You're Building a Feature, Product, or Business

Before pouring resources into a venture, entrepreneurs should honestly assess which category their idea falls into:

"Is this a business, is it a product, or is it a feature? If it's a feature, that's something that could just be added on to an existing business."

She illustrates this with the example of a photo-uploading service for Twitter that became obsolete once Twitter incorporated that feature directly into its platform.

5. Character Matters

Perhaps most importantly, Heather emphasizes the significance of integrity in business:

"Being a good person matters. Keep that in mind and do the work, keep your head down, and you'll get to where you want to go."

Conclusion: The Journey from Farm to Tech Success

Heather Udo's journey from a Wisconsin farm to becoming the CEO of a software company with 500 million SKUs exemplifies how early life lessons in independence, work ethic, and problem-solving can translate into entrepreneurial success. Her story highlights the value of entry-level experience, the importance of building the right team, and maintaining a solution-oriented approach to challenges.

For aspiring entrepreneurs, Heather's advice to focus on revenue potential early, strategically evaluate what to build versus partner on, and carefully assess whether you're creating a feature, product, or business provides a practical framework for startup decision-making.

Throughout her career, Heather has demonstrated that entrepreneurial success isn't just about innovative ideas or technical skills—it's about building resilient teams, focusing on solutions rather than blame, and maintaining integrity throughout the journey. As she continues coaching first-time founders while leading Shoppable, her experiences offer valuable lessons for anyone looking to navigate the complex world of tech entrepreneurship.