From Serendipity to Cybersecurity and the Inc. 5000: The Story of Defendify’s Rise

The story of Defendify starts modestly—two entrepreneurs, a mutual connection, and a simmering startup scene in the small, coastal city of Portland, Maine. Little did Rob Simopoulos and Andrew Rinaldi know that what started as a call for a cold beer would end in a life-calling to make cybersecurity possible for small and midsize organizations and ignite a journey to the top 25% Inc. 5000 list in seven short years.

Rob, a seasoned security industry veteran, had moved to Maine from Toronto after successfully exiting his first company in Canada. Then, while building one of the leading security integrators in the US, he couldn’t help but see the imminent convergence of IT, security, and cybersecurity. With new business ideas swirling, all he needed was the right partner to dive in with.

One of Rob’s best friends—a doctor, not your everyday founder—not only knew his passion but how to address that missing link. He encouraged Rob to meet his cousin, sharing “I know you both better than anyone, if you two get together, you will build something epic”.

Enter Andrew, another entrepreneur who had migrated to Maine with a passion for building great things. His track record seemed to coincide, bringing together a blend of business, product, and operational excellence across multiple companies including co-founding and growing for over 15 years one of Boston’s first digital design and development agencies.

As the two chatted the pieces began to fall into place. Andrew, no stranger to the challenges of IT security in the small business and midmarket, quickly saw the tremendous potential in Rob’s cybersecurity vision. By the time they left that meeting, they had their very first “cybeer” and the start of a partnership for the future.

From their humble beginnings sharing a 90 square foot office designed for a single person, Rob and Andrew (sitting back-to-back) set out to tackle the unique cybersecurity needs of small and midsize businesses. They knew these organizations from the inside out and quickly understood how they faced the same regulatory pressures and cyber threats as their larger counterparts but lacked the resources to keep up. IT teams were stretched thin, juggling everything from email and infrastructure to “the cloud” and tech support, with little time left for cybersecurity.

But Rob and Andrew had a plan: they could “democratize cybersecurity”, bringing enterprise-level protection to every business—regardless of size and budget. And so, Defendify was born.

It’s a story rooted in a whole lot of determination and a little bit of serendipity— a reminder that sometimes, the greatest ideas can come from unexpected people and in unexpected places.

A lot can change in a day—and it did

Rob and Andrew initially intended to establish a small team of consultants who could work with non-enterprise organizations to assess existing security controls and recommend improvements, build policies, train employees, and deploy technology. With that, they went searching for tools that could help.

In the spring of 2017, they traveled to a cybersecurity conference in Boston, under two hours south of Portland. To their surprise, virtually every vendor shared the same sentiment: “If you aren’t going after enterprise accounts with thousands of users, we’re not interested”.

Driving back to Portland, the pair discussed the vendors’ surprising feedback. It became clear that the problem they sought to solve was even bigger than they originally thought. Not only did small and midsize organizations need these security solutions to protect themselves, but they also lacked the bandwidth to deal with dozens of vendors—especially those almost exclusively focused on large enterprises.

Equally disappointed and perplexed, Rob asked, “Why doesn’t cybersecurity in a box exist for the SMB? Can we build that?” Andrew quickly understood the opportunity. “Yes, we can build that!” In an instance the simple idea to build a cybersecurity consultancy to help small and midsize organizations, became a vision to democratize cybersecurity through a unified platform accessible by all.

The small and midmarket challenge

Andrew and Rob understood that small and midsize organizations were stretched thin with existing workloads, and their security controls were limited, often to just antivirus on endpoints and firewalls for network security. Few had dedicated security teams to help assess their posture, build policies, train teams, and deploy technology. But they needed all these things and more, especially given rapidly growing regulatory, compliance, insurance, and third-party vendor risk requirements.

From their experience, both having built and scaled multiple businesses, Rob and Andrew were keenly aware that existing enterprise solutions required too much management and financial overhead for these organizations. They also understood that home office and “small business” solutions were often designed for consumers and lacked the features, scalability, and level of protection required by fast-growing small and midmarket organizations.

The sweet spot would be to develop a platform, designed with automation and usability in mind. It needed to provide the suite of solutions IT teams needed, bringing together multiple layers and features of security in one package. Comprehensive protection, easy to understand, easy to use, and with world class support. And it needed to be cost-effective, not cost-prohibitive.

Up and going and growing

Released in August 2018, the Defendify unified cybersecurity platform was extremely well-received by existing test pilots to new accounts alike. Fast forward 18 months; the COVID pandemic arrived and changed the world. From an IT and security perspective, it forced organizations to quickly institute remote work, stalling projects and increasing uncertainty.

For Defendify’s target customers, the pandemic dramatically increased workload while heightening the need for stronger security. IT teams everywhere were suddenly faced with building and troubleshooting home and remote offices. Within weeks, IT teams were forced into managing cybersecurity and in a vastly different environment. The shift required new technology and introduced new cybersecurity threats. Teams needed to move quickly to provide guidance, rules, oversight, and training.

“How can we help?”

As entrepreneurs, Rob and Andrew were conditioned to problem solve when faced with challenges. They had previously worked through recessions, downturns, and other adverse situations. While they hadn’t seen it all, they had seen a lot. The pandemic was obviously different.

Defendify adopted a strategy of, “How can we help an IT community who is facing new challenges – but whose budgets are frozen?” The result was Defendify’s Essentials Package, a free offering of the Defendify platform to address three core requirements for starting a cybersecurity program: cybersecurity assessments to help teams target weaknesses, vulnerability scanning to identify unpatched applications and components in IT infrastructure, and curated threat alerts to stay on top of developing cybersecurity news and notifications.

The response from the market was overwhelmingly positive, with hundreds of midsize teams quickly subscribing to and benefiting from the free Essentials package. Today, thousands of organizations worldwide use Essentials.

Expanding the platform

The original platform provided IT teams with strong tools for assessing risk, testing resilience, and building policies and training programs. As cyberattacks continued to increase, it became clear that busy small and midsize organizations needed help defending against attacks. With smaller IT teams and limited budgets, they couldn’t monitor their systems for attacks 24 hours a day, nor could they afford the millions of dollars needed to build and staff their own Security Operations Center (SOC). Defendify again saw an opportunity to help. In 2020 it added its Managed Detection and Response (MDR) solution to the platform. The MDR offering enabled small and midsize organizations to deploy the same early response and threat hunting capabilities normally found only in large enterprises, and have attacks responded to by cybersecurity experts 24/7/365, without the overhead of building and staffing a dedicated SOC.

In a year of unprecedented change, strategic moves by Defendify—through its free product and 24/7 coverage options—served to both help customers and catalyze the company and its growth.

As they expanded their market and Defendify’s reputation grew, so too did its customer base—both in size and nature. Alongside smaller businesses, larger midmarket organizations, unhappy with solutions that required constant oversight and dedicated personnel, began to adopt Defendify. As word spread, Defendify added customers in over 60 countries. Recognizing that understaffed IT organizations needed attentive support and driven by a culture of making things easy and never leaving anyone hanging, Rob and Andrew added a customer success team to guide customers in building and maintaining their cybersecurity programs.

By focusing their business on helpfulness, vigilance, and product-market fit, Defendify’s growth accelerated quickly.

The Inc. 5000

Being recognized on the Inc. 5000 list is an important milestone to Rob, Andrew, and the entire Defendify team. “It’s a testament to what we’ve been doing”. said Andrew, “We look at the list every year and think how amazing it would be to join the ranks. Well, here we are, and we couldn’t be more grateful. We truly owe it to everyone around us, including our customers and team. The validation and recognition of everyone’s hard work is truly fulfilling”.

What’s next for Defendify?

Making the Inc. 5000 list of fastest-growing privately owned companies in the United States is a remarkable achievement. Rob and Andrew reflect on it being the culmination of years of hard work but know that in many ways their work has just begun.

The cybersecurity market is changing daily as criminals adopt new tactics and continue to target small and midsize organizations. The key to Defendify’s evolution – and success – continues to be listening to its customers.

“It all goes back to making our customers’ lives easier,” said Rob. “This means ‘democratizing security’, making the high level of security previously available only to large enterprises accessible to organizations of any size.”

Making cybersecurity possible for all is a grand vision and mission. You’ll be glad to know, Defendify is on the case.