Best in Business: 9 Questions With Highspot Co-Founder Robert Wahbe

Wahbe applied what he learned at Microsoft to his own company.

Robert Wahbe is the co-founder and CEO of Highspot, the industry’s highest-rated sales enablement solution that sales reps and marketers love. Prior to Highspot, Robert was corporate vice president of marketing for the Server and Tools Division at Microsoft, and co-founder and CEO of Colusa Software, which was acquired by Microsoft. 

In this installment of GOBankingRates’ “Best in Business” series, which profiles the people behind some of the top innovative companies, we chat with Wahbe about why understanding customer needs is so vital to starting a successful business.

When did you know you had to start this company?

The idea for Highspot came when I experienced a market pain point firsthand in my role as the CMO for Microsoft’s Server and Tools Division. We had more than 10,000 pieces of content, but there was no way to ensure our sales reps had the assets they needed to be effective when engaging with prospects and customers. I learned this was a widespread challenge after speaking with other large enterprise companies experiencing the same difficulties.

What led me to found Highspot was discovering the opportunity to solve an important problem in the business world, and also the fact that I have always been attracted to startups — it’s very satisfying to build something from scratch and be a part of a team from the beginning.

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What were your biggest fears about launching your own business?

Two primary concerns almost all entrepreneurs share when launching a company are: finding product/market fit for a large market and ensuring a sustainable competitive advantage. It can be very difficult to develop a product that companies are willing to invest their time and money in — it’s a really high bar, especially for the enterprise. You have to add a tremendous amount of value.

After establishing product/market fit, the next fear is if you will be able to sustain a competitive value over the years. Your product needs to be transformatively better than what exists in the market. You can talk to customers, you can do focus groups and you can do all the right research, but ultimately, your fears won’t be put to rest until your customers show you through choosing your company that your product has both product/market fit and the competitive edge.

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What was the most surprising thing about the process?

One of the most eye-opening learnings was just how much you need to deeply engage your customers about what their problems are, what they’re trying to solve and what solutions they’re considering. Gaining a holistic understanding of an organization’s problems, including challenges for individual employees, is crucial to achieving product/market fit and ensuring you build a product that can evolve to meet changing needs. During Highspot’s early days, we spoke with customers constantly, which was essential to helping us hone both our product and marketing message.

What was the hardest part?

When you first launch a product, you have to work to establish a customer base and repeatable business. Until this happens, it can be difficult to pinpoint what’s working and what’s not. Is your product adding real value? Is the market large enough? Is your marketing wordage effective? These questions are challenging to answer when your feedback is limited. Once you have customers and inbound inquiries at scale, you can begin to experiment with new ideas to find what works best and make optimizations based on real-life observations and results.

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Read: 90% of Startups Fail Within 3 Years — Here’s How One Entrepreneur Is Staying Afloat

Did any previous jobs inspire you to run Highspot the way you do?

Establishing and maintaining a great company culture has been a priority since day one. Having experienced a variety of cultures at different companies, I knew we needed to establish a place where people felt inspired and stretched to do their best work. Highspot’s culture can be defined as supportive, collaborative and transparent, and we are thoughtful about hiring people who help make our office a positive, energizing environment.

In the past, I have sold successful software that did not emphasize design. Upon founding Highspot, a big focus for us was building a product that was not only successful but was also beautifully designed and easy to use. One way we did this was by taking a modern, interactive approach to development. Rather than going through a traditional linear process, which often leads to pedestrian software, we structured the entire engineering and product effort around the notion of iteration and collaboration — two things that great software requires.

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Who are the people you lean on most?

Three groups of people have been instrumental to the successful launch of Highspot: my family, co-founders and early employees, and early investors. Having the support of your family is hugely important because startups are hard and can be stressful. Your co-founders are also critical — you need to be surrounded by people who execute under pressure, innovate as a team, refrain from finger-pointing and keep a can-do attitude at all times. Early employees also come into play as they contribute to forming the culture and perform a wide variety of responsibilities that are crucial to getting the company off the ground. Finally, your first investors who believe in your company against all odds play a vital role in taking your business to the next level.

What advice would you give to someone who wants to start their own business?

Listen to your customers and focus on your product — make it great. A lot of companies get great traction early on, but they cannot sustain it because they don’t fundamentally understand their customers or the product, or how to build upon it and make it scalable. Your product is the engine of your company. It fundamentally drives your business, so do the work to understand it, hire the right people to work on it and build it in a way that solves your customers’ needs. You will need a product that you can evolve quickly. That’s one thing that’s very special about Highspot — our engineers built our core architecture in a way that allows us to innovate faster than anyone else, and that’s a critical competitive advantage.

When did you realize Highspot was going to make it?

We realized that we were on the right track when we began having large organizations adopt our solution, and tell us that it completely transformed how they enabled their sales teams to be more effective. Those early signals from our first customers proved that Highspot worked in the real world at scale. This is a difficult thing to know until it actually happens. The incredible feedback we received following a large number deployments was the sign we needed to tell us that we really had created the industry’s most advanced sales enablement solution that sales reps love.

How do you define success?

On the business front, I define success as adding value to our customers. I get the most satisfaction out of seeing the positive impact our solution has on our customers’ businesses every day. We are really helping their companies grow and flourish — and that, to me, is success.

Click through to read more about success strategies for new entrepreneurs.

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This interview has been edited and condensed.

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About the Author

Gabrielle Olya

Gabrielle joined GOBankingRates in 2017 and brings with her a decade of experience in the journalism industry. Before joining the team, she was a staff writer-reporter for People Magazine and Her work has also appeared on E! Online, Us Weekly, Patch, Sweety High and Discover Los Angeles, and she has been featured on “Good Morning America” as a celebrity news expert. 

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