Unlocking Your First Customers: Expert Strategies for Tech Startups Looking to Win and Retain Customers

by Taylor McAuliffe

Customer acquisition is one of the most challenging yet most important parts of leading a startup. The secret to sustained success for tech startups isn’t just about creating a cutting-edge product, it’s about acquiring and retaining the right customer. But how do you do it? We’ve had the pleasure of talking to seasoned professionals who have provided insight into the best approaches for sales and finding customer success that will bring those first customers through the door and keep them coming back for more.

Sales is an essential component of the acquisition toolkit but often the hardest to use right. We spoke to Robert Simon, VP of Strategic Sales at NOW Vertical Group. Simon is a dynamic, performance-driven sales executive on the leading edge of selling digital disruption and transformation. Simon shared his experiences selling transformational technologies and the levers to pull to create an effective sales strategy and process that drives revenue outcomes.

The first thing to get straight: your Ideal Customer Profile (ICP). Understanding and creating an exceptionally clear link between how your audience views their pain point and how your product/service will resolve it is core to your sales process from the very beginning. Value comes from considering the buyer’s perspective and understanding what this pain point truly costs them.

“Your buyer never shows up to buy anything. They show up to do their job. You need to be really clear on their reasoning to buy something and understand what the pain is that is driving that. Get that codified or written out and then understand how your value proposition maps to that or doesn’t. It may not be perfect, but you need to understand where there is a really good connection between where you see pain in the sector with your particular buyer and how you think that you can resolve that.”

As Simon reflects, understanding why your customer fundamentally needs a solution is necessary for your customer acquisition strategy. Fall in love with the issue you are solving, not the product. Once you understand the problem, you can develop your value proposition to help effectively communicate the unique way your product will solve their problem. As well, it impacts branding and the ability to make your solution relevant and meaningful to potential clients.

Watch Robert Simon’s episode of Tech Uncensored to learn more about how successful sale outcomes are being driven by the right composition of individuals and process.

Determining your customer’s pain point may seem easy enough, but how do you accomplish this?

In a recent interview with Faheem Rauf of Rauf and Associates, we learned that listening is another important aspect of successful customer acquisition. Rauf is a seasoned sales professional with experience coaching and leading big-name clients, including Ford Motor Company, Bank of Canada and HBO, among many others. He shares that while it may seem backwards, the more time you spend listening to a client, the more opportunity there is to make a sale. Actively listening to clients, understanding their unique needs and tailoring approaches accordingly is the recipe for effective selling.

“In selling, there’s nothing such as asking too many questions. That does not exist. I’m asking the question to understand the processes, to make sure that I come back with a proper solution.”

Every time your prospective client opens their mouth, it gives you an opportunity. The more you know about the client, the better you can serve them. They will tell you what is worrying them, and from there, you can evaluate if there is a fit with this client and if there is an opportunity for your product/service to address their problems in a meaningful way.

Unfortunately, you will often listen to a potential customer and realize their pain points are not the right fit for your product. As a result, customer acquisition requires a frustrating quest for product/market fit that all founders experience. Rahul Vohra, CEO of Superhuman, knows this better than anyone.

While building Superhuman, Vohra struggled to find the sweet spot for success, where his product aligned perfectly with the needs and demands of his target market. Reflecting on his experience, Vohra shares the toll this took on his ability to launch:

“I felt this incredible pressure to launch, but I also knew that if we did, it would go very badly…I couldn’t just convey this to the team, who had invested their hearts and souls into the product…I needed a plan”  

Yet, his experience has allowed him to create a toolkit for other founders that can guide them toward conquering the challenges of product-market fit.

“I spoke to all the experts and read everything I could find, and what I found was a way to define product-market fit, a metric to measure product-market fit and even a methodology to systematically increase product market fit—which I know sounds crazy.”

The Superhuman Product-Market Fit Engine has become a standard reference for measuring product market fit. It uses insights from areas where product/market fit is not happening to unlock where you can improve and turn passive users into superfans.

Finding a product/market fit is most useful at the beginning of a startup’s journey. This fit anchors many other processes startups should employ from the get-go, including connection with customers and branding.

Read more about Vohra’s startup journey and the work he is doing to help other founders fuel their startup growth.

Securing and retaining customers is one of the hardest things to do in a startup environment. You start out with zero customers but believe you have something worth buying. Finding those first few customers can be a long and excruciating process. Learning from the experiences of other founders and those involved in the startup environment who have seen other founders secure this first 1% is a great way to improve your customer acquisition strategies.

Altitude reaches out to experienced founders and professionals in all realms of business to provide founders with the guidance and support they need to grow and scale their startups. Through our RevUp, Growth Essentials and Investor Readiness programs, startups can accelerate their growth and build their business correctly. Find out more here. For more information, please email us at


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