Rob Rosenberger: Transforming the Marketplace with Effective Best Practices Powered by Technology



Blackdragon is the first and only of its kind, matchmaking platform helping companies to win contracts with the US Government. As the largest and fastest-growing bid and proposal (B&P) firm throughout the federal industry, Blackdragon is a global coalition of freelance experts available to work on-demand via arobust portfolio of fixed-price products, and services. These outcome-oriented products/services that help bidders win contracts are high quality, tailored to each pursuit opportunity with fast turnarounds, and are much more cost-effective than conventional approaches like hiring individuals by the hour.


The Visionary Behind the Company

Rob Rosenberger is the Founder and CEO of Blackdragon. Like CEOs of large companies who spend years being groomed and educated before taking the reins, he too gained leadership experience working across different departments of major corporations, receiving coaching and advice. Conversely, he is like most start-up founders who spearhead innovation by making a new technological discovery, identifying an underserved need, and having a great vision for how an industry can be improved. Rob created this distinctive business as a former corporate leader previously accountable for winning new contracts to keep the organization healthy and profitable. Blackdragon was conceived from the mindset of competitive business leaders responsible for growth, desiring a better alternative to winning contracts compared to repeating obsolete processes yielding unimpressive results.


The Journey of Becoming a CEO

Rob was raised on a large Texas ranch and grew up learning about hard work, being responsible for chores, and contributing to larger outcomes. Although he played team sports in school which taught important lessons in discipline and competitiveness. His first business began when he was 9 years old selling watermelons which he continued until college. Those experiences shaped Rob’s fundamental business aptitudes and formed the baseline for his leadership skills. By age 16, the visionary had built and commanded a workforce of 42 employees throughout East Texas selling tens and thousands of melons nationwide each season.

Later attending Texas, A&M University (TAMU), Rob became an active member of the Corps of Cadets ROTC program. Before graduating, he left college to join the US Navy where he flew classified missions in a reconnaissance squadron during the first Gulf War. Returning to TAMU after the Navy and graduating with double majors and double minors in business, Rob was recruited to the CIA where he was trained in negotiating sophisticated international contracts and administering the business aspects of complex projects on an enterprise-scale spanning the globe. There, he attended multiple universities during off-duty hours completing four graduate programs in business. He later departed CIA to become Special Adviser on federal contracting to the Joint Staff in the Pentagon.

Earning corporate leadership roles of increasing scale and responsibility, Rob ultimately attained the rank of Chief Operations Officer (COO) for a midsized federal contractor firm. Shortly thereafter, he was hand-selected by a US Congressman to join his staff as a Congressional Fellow where Rob advised him, other Members of Congress, Senators, and various committees throughout the House and Senate. In 2015, Rob launched Blackdragon and said goodbye Capitol Hill.


Primal Challenges During the Expedition

Winning federal contracts has been exponentially more challenging for a long time. Combined effects of advancing technology with the rise of the Gig Economy and disruption of COVID-19 have only amplified those challenges. There is no turning back. Companies clinging to outdated ‘industry best practices’ (repeated internal processes applied the same way to every target opportunity in the pursuit of maximum efficiency) and relying on ‘rainmakers’ is no longer a competitive recipe for winning contracts in the new normal. Today’s successful contract winners are bidding smarter, more cost-effectively, and on a greater scale than ever before. The key to winning on a sustainablie basis is to always do something no one else has yet done, in inventive ways, with lower risks,more volume, generating better return on investment.

In his Blackdragon journey,Rob faced challenges during the initial phase of a revolutionary new business model. A common challenge to being a first of its kind business with fresh thinking in an old industry is the slow rate of early adopters willing to try unfamiliar solutions.This was especially applicable given most federal contractors are risk-averse focusing more attention and resources on operational efficiency than competitive effect.Too many do not ‘play to win’ but rather ‘play not to lose,’ which is not the same. While those playing to win embrace new ways of operating and have defined strategies being constantly adapted, bidders playing not to lose typically operate in a reactive mode trying to optimize what they are already doing in their routine game plan. Blackdragonisthe first to offer a progressive“shared-risk” business model contrary to traditional hourly consultants who get paid regardless of whether a contract is won, which often comes across astoo good to be true. As a result, early clients were careful to experiment with Rob’sin genious solutions combining technology, predictive analytics, and crowd sourced “dream teams of expert freelancers for each project to maximize the probability of winning.”This further led Blackdragon to instituting a ground-breaking proposal development methodology for consistently creating more competitive proposals compared to obsolete standard practices.


Vital Attributes that Emerging CEOs Should Possess

According to Rob, the vital attributes which every CEO must possess are sets of culture baseline for the company. A CEO should be an opportunistic risk-taker balanced with vigilant reluctance from being erratic or reckless. He/she should be capable of boldly disrupting conventional traditions with innovation while practicing pragmatic approaches for maintaining priorities at a realistic pace for the organization. Rob advocates that decisiveness with speed and conviction must be backed by plenty of grit and courage. He adds to this by saying that the CEO works towards inspiring employees in taking initiative and performing at their best.


Unique to Blackdragon

Blackdragon has successfully pioneered innovative fixed price solutions for bidder clients unlike any that have ever existed. Until Blackdragon, bidder companies are left to identify, analyze, qualify, and win targeted contracts almost exclusively with humans via a combination of full-time and part-time employees augmented by individual freelancers paid by the hour. This imperfect approach is expensive, unreliable, inconsistent, risky, a headache to manage and it does not scale.

Rob states that Blackdragon has a profound understanding of its clients because most of its freelance experts (aka, Dragons) have extensive careers working throughout this industry which is notorious for its resistance to change. Instead of doing things the same way it has always been done, the company has developed internal processes for creating compelling solution ideas from the knowledge and experience of our constantly expanding community of expertise.


Role of Disruptive Technologies 

Rob believes technologies such as artificial intelligence, IoT, automation, cloud computing, big data and robotics are modifying business models across every industry unlocking enormous market opportunities. He says that there are two types of innovations: transitional and transformational. Transitional innovation simply sustains the existing business outlook and system structures but does not equip the organization to handle significant market shifts. Transformational innovation (also called “disruptive innovation”) fundamentally goes against the ‘business as usual’ outlook. The role of leaders has changed over the years requiring them to be increasingly adept at directing transformational innovation more than transitional.

Rob takes pride in talking about Blackdragon as the first to use advancing technologies such as business intelligence, and big data, modelling/forecasting, and social connectivity to form on-demand comprehensive Dream Teams of ‘just right’ crowd sourced experts to create each product purchased by a client.


Word of Wisdom to Budding Leaders

On advising to emerging business leaders, Rob says successful business leaders need to master the skills that will allow them to work anywhere in today’s dynamic business world. He suggests new leaders should think bigger and faster. Barriers to boldness and speed are less about technical limits and more about things such as mindsets toward what is possible, what people are willing to do, the degree to which implicit or explicit policies that slow things down can be challenged, and bureaucratic chains of command. “Given the effects of the global pandemic, tomorrow’s leaders must be creative about how they select, train, coach, recognize and reward their employees”, he adds.


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