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What's a Risk You Took That Paid Off for Your Organization?

What's a Risk You Took That Paid Off for Your Organization?

In the spirit of bold entrepreneurship, we've gathered insights from ten business leaders, including Founders and CEOs, on the pivotal risks they took that propelled their companies forward. From scaling teams for committed growth to diversifying into legal transcription services, these trailblazers reveal the game-changing decisions that led to significant organizational growth or improvement.

  • Scaled Team for Committed Growth
  • Expanded Cybersecurity Service Offerings
  • Embraced Agile Product Development
  • Invested in Cutting-Edge Technology
  • Pivoted Based on Customer Feedback
  • Opened Second Location for Market Expansion
  • Shifted Focus to E-Commerce
  • Co-Developed Custom Virtual Staging Tool
  • Transitioned to Subscription-Based Web Services
  • Diversified into Legal Transcription Services

Scaled Team for Committed Growth

I made the decision at my previous company, Write Right, to scale rapidly by hiring full-time employees instead of relying on freelancers. Over 14 months, I grew the team from 25 to 75 employees. This choice was driven by the need to build a committed team that could align with the company’s goals and grow alongside it.

Having full-time staff improved our communication and allowed us to work on long-term projects more effectively. Although it was a financial risk, it led to better results, with higher client satisfaction and a stronger, more cohesive team. This decision ultimately played a significant role in the company’s growth.

Bhavik Sarkhedi
Bhavik SarkhediFounder & Creative Director, Ohh My Brand

Expanded Cybersecurity Service Offerings

I considered taking the risk of growing the company and expanding the scope of rendering services to include testing of information systems for cybersecurity and cloud security assessments. It was something new for us then, increasing the need for capability investments. Certainly, as more and more companies moved toward the cloud and embraced security, this made us a vendor that clients could turn to to protect their applications and infrastructure. This step not only broadened the range of the accounting company’s income potential but also brought in new clients and, as a result, significant growth for the organization.

Khurram Mir
Khurram MirFounder and Chief Marketing Officer, Kualitatem Inc

Embraced Agile Product Development

One significant risk we took at CarePatron was fully embracing an agile product-development approach when releasing Version 1 of our platform. Instead of waiting to perfect every detail, we launched the initial version and actively shaped it through ongoing customer feedback. By taking this risk, we positioned ourselves to respond quickly to our users' real-world needs, continuously refining and improving the platform based on their input.

This iterative process not only enhanced the quality and relevance of our offerings but also built strong relationships with our users, who felt directly involved in the product’s evolution. The agile approach, while risky, ultimately led to significant growth for CarePatron, allowing us to deliver a product that genuinely meets the needs of healthcare professionals and their patients.

Jamie Frew
Jamie FrewCEO, Carepatron

Invested in Cutting-Edge Technology

One significant risk I took involved investing in a cutting-edge technology platform that was unproven in our industry but promised substantial efficiency gains. Despite the initial cost and uncertainty, I believed that adopting this technology could dramatically enhance our operational capabilities and offer a competitive edge.

The decision proved to be transformative. Implementing the new platform streamlined our workflows, improved data accuracy, and significantly reduced processing times. This led to increased productivity and allowed us to scale our operations more effectively. While the risk was considerable, the successful integration of the technology not only delivered substantial growth but also positioned our organization as a leader in innovation within our sector. This experience reinforced the value of calculated risk-taking in driving long-term success.

Shehar Yar
Shehar YarCEO, Software House

Pivoted Based on Customer Feedback

One significant risk I took that led to substantial growth for RecurPost was the decision to pivot from our original product direction based solely on customer feedback. Initially, we were focused on a broader social media management tool, but we noticed a consistent demand for a more specialized solution that could automate content recycling for small businesses and entrepreneurs. This wasn't part of our initial roadmap, and pivoting meant reallocating resources and potentially alienating some of our existing users. However, I trusted the feedback and saw an opportunity to fill a niche that was underserved. We took the leap and invested heavily in developing features specifically for content repurposing and automation.

This decision was a turning point for us. Not only did it differentiate RecurPost in a crowded market, but it also led to a significant increase in user engagement and retention. We saw our customer base grow rapidly because we were solving a specific pain point that other tools were overlooking. By embracing this risk, we not only refined our product but also defined our unique value proposition, which has been instrumental in our continued growth and success. The experience taught me the importance of listening to our users and being agile enough to make bold moves when the data points in a new direction.

Dinesh Agarwal
Dinesh AgarwalFounder, CEO, RecurPost

Opened Second Location for Market Expansion

A few years ago, I decided to expand my car detailing business by opening a second location across town. It was a huge risk financially because the market there wasn't as established, and I wasn't sure if we'd have the same loyal customer base. But I saw the potential in reaching new clients who didn't want to travel to our original location.

The gamble paid off. Not only did we attract new customers, but the second location quickly became just as busy as the first. This expansion allowed us to double our revenue in under a year and cemented our presence as a leading car detailing service in the city. It taught me that sometimes, taking a calculated risk is the only way to unlock new growth opportunities.

Ryan Farook
Ryan FarookOwner, Ryans Mobile Car Detailing

Shifted Focus to E-Commerce

A big risk I took in my floral business was stepping back from having a traditional storefront to focus more on e-commerce. It felt risky at the time because there's something comforting about having that physical presence, but I noticed that more and more people were shopping online for flowers. So, I invested heavily in building out my online store, focusing on improving the website and boosting my digital marketing efforts.

This shift allowed me to reach far beyond my local area and serve customers I wouldn't have been able to with just a brick-and-mortar shop. It also freed up resources to experiment with new products and streamline my operations. In the end, that leap into the digital space helped me grow my business, reduce overhead, and find new ways to connect with customers that I didn't even know were out there. It was one of those risks that felt uncertain at first but ended up being the best decision I could have made for long-term success.

Sophie Marasco
Sophie MarascoFounder, Thanks A Bunch Florist

Co-Developed Custom Virtual Staging Tool

A standout risk for us was partnering with a tech startup to co-develop a custom virtual staging tool tailored specifically for luxury properties. It was a bold move because it meant putting significant resources into a project with no proven market. We were betting that this specialized tool would fill a niche need and offer something unique in the luxury real estate market.

The gamble paid off handsomely. The new tool allowed us to create hyper-realistic, high-end staging visuals that set us apart from our competitors. Luxury real estate agents were particularly impressed, leading to high-profile projects and an increased reputation in that market segment. It was a risky venture, but it was something that would change everything for our brand and showcased our commitment to innovation and excellence.

JD Lloyd
JD LloydBusiness Development Manager and Project Manager, Bella Virtual Staging

Transitioned to Subscription-Based Web Services

As the founder of Mango Innovation, one risk that led to significant growth was transitioning to a subscription-based model for web development services. The web development industry perpetuates the myth that quality, speed, and affordability are mutually exclusive. I knew we could shatter this illusion by offering flexible subscriptions with unlimited requests.

To make this work, I had to invest in systems and automation to scale our services while maintaining high quality. The initial costs and implementation challenges were daunting, but the potential was huge. Within a year of launching, we tripled our client base and monthly revenue. More importantly, we opened up new opportunities for clients by providing web solutions tailored to their needs and budget.

The key was focusing on execution and client satisfaction. We provided white-label services that seamlessly integrated with our clients' brands using a mix of WordPress, Shopify, and custom development. This allowed us to meet tight deadlines without compromising quality. We also offered month-to-month terms so clients could scale up or down as needed.

For any service-based business, embracing productization and a subscription model can transform your growth. You have to believe in your ability to shatter industry myths by leveraging technology and a client-centric approach. Start with a pilot program, learn from client feedback, and scale from there. The results will speak for themselves.

Derrick Boddie
Derrick BoddieSenior Web Developer & Founder, Mango Innovation

Diversified into Legal Transcription Services

Expanding Ditto Transcripts beyond medical transcription was a pivotal risk that led to significant growth. We ventured into the legal and law enforcement sectors, which required new investments in expertise and marketing. Although it was a challenging transition, the decision paid off by diversifying our client base and making the business more resilient. This move fueled our growth and positioned us to better withstand market fluctuations in any single industry.

Ben Walker
Ben WalkerFounder and CEO, Ditto Transcripts

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