Samuel “Sam” Hollander is an accomplished commercial growth executive, entrepreneur, and strategic advisor with more than 20 years of experience building businesses, accelerating revenue, developing strategic partnerships, and transforming market opportunities into sustainable commercial success. Throughout his career, he has established himself as a forward-thinking leader who combines entrepreneurial vision with operational discipline, helping organizations navigate complex business challenges while identifying new pathways for growth. His expertise spans technology, advertising technology (AdTech), healthcare marketing technology, digital media, data intelligence, enterprise sales, and business commercialization. Guided by his personal philosophy, “Protect what works. Question what doesn’t. Build what’s next,” Samuel approaches leadership with intellectual curiosity, sound judgment, and a commitment to creating lasting value for businesses, their stakeholders, and the people who power them.
Currently serving as Senior Vice President of Sales and Partnerships at OnSpot Data, Samuel works directly with the company’s founders and executive leadership to accelerate commercial growth, strengthen strategic partnerships, and expand market opportunities. Since joining the organization in 2024, he has helped establish its East Coast commercial presence, building enterprise relationships and developing business across healthcare, retail, automotive, and media agencies. His accomplishments include securing approximately $2.2 million in projected first-year contract value against an $800,000 personal goal and closing a $263,000 healthcare marketing engagement with RiverSpring Health. Beyond revenue generation, he collaborates with product, analytics, and executive teams to translate emerging customer needs into innovative offerings, stronger market positioning, and scalable commercial strategies. His involvement in strategic discussions with senior leadership and board members reflects his ability to connect immediate business priorities with long-term organizational objectives.
Samuel’s entrepreneurial leadership is further demonstrated through Mango Media Advisors, the consulting practice he founded in 2020 to help emerging and established businesses strengthen their commercial foundations. As Founder and Principal, he advises entrepreneurs, founders, and executive teams on go-to-market strategy, product commercialization, pricing, revenue infrastructure, strategic partnerships, and business development. His advisory work has helped generate more than $1 million in early-stage revenue, increase commercial pipelines by approximately 60% for a digital out-of-home technology business, and improve partner acquisition by approximately 20% for an artificial intelligence and measurement company. Through these engagements, Samuel has developed a reputation for identifying overlooked opportunities, challenging conventional assumptions, and bridging the gap between business strategy and execution. His work reflects a conviction that meaningful growth is not simply about increasing sales activity, but about building the right products, partnerships, systems, and organizational capabilities to sustain success.
One of the defining chapters of Samuel’s career was his role as Co-Founder and Chief Digital Officer of Enlighten, an innovative advertising and retail technology company that helped pioneer programmatic advertising solutions for the cannabis industry. Joining the business in 2020, he played an instrumental role in developing its commercial model, building its advertising technology capabilities, establishing enterprise partnerships, and scaling revenue from its earliest stages. Under his commercial leadership, Enlighten generated approximately $5 million in advertising revenue in less than two years, driven entirely by new business. He also helped create approximately $2 million in incremental revenue through expanded digital out-of-home inventory, technology integrations, and strategic partnerships. A pivotal achievement was negotiating a $1.1 million advertising and technology licensing agreement with Weedmaps, which helped initiate acquisition discussions. As a founder, equity holder, and member of the negotiating team, Samuel contributed to Enlighten’s eventual $29.4 million acquisition by Weedmaps, demonstrating his ability to build enterprise value through commercialization, strategic positioning, and disciplined execution.
Following the acquisition, Samuel transitioned into senior enterprise leadership at Weedmaps, serving as Senior Vice President of Sales and leading a 20-person organization responsible for strategic enterprise relationships and commercial expansion. In this capacity, he delivered 110% year-over-year growth while maintaining nearly 100% customer retention. Working closely with the Chief Operating Officer and Chief Revenue Officer, he strengthened organizational structure, established forecasting and accountability processes, implemented consultative sales frameworks, and improved cross-functional collaboration. He also contributed to the commercialization of an analytics platform that delivered approximately four times return on investment for customers. This experience further refined his ability to lead through organizational change, integrate entrepreneurial innovation into larger business structures, and align commercial performance with broader corporate strategy.
Earlier in his career, Samuel held leadership positions at UberMedia, where he spent more than four years advancing enterprise sales, data-driven advertising solutions, and strategic business relationships. Progressing through increasingly senior responsibilities, he ultimately served as Vice President of Sales, generating approximately $8.9 million in new-logo revenue and contributing to 325% year-over-year growth. His success was driven by an ability to translate complex technologies involving geolocation, audience intelligence, identity, and measurement into practical business solutions for major brands and advertising agencies. He also improved sales conversion and operational efficiency by more than 50% through stronger qualification processes, commercial packaging, and go-to-market execution. Following UberMedia’s acquisition by Gimbal, Samuel was retained in a commercial consulting capacity to support the integration and commercialization of the combined companies’ offerings. His participation in these acquisition-related transitions provided valuable insight into how strategic alignment, operational integration, and revenue execution contribute to long-term enterprise value.
Samuel’s professional foundation was built through influential roles across sports, entertainment, media, and advertising. At Whistle Sports, he helped establish the company’s first programmatic monetization offering, generating approximately $3.4 million in new revenue and increasing advertising yield by approximately 22%. At National Geographic, he developed integrated advertising partnerships across digital, print, social, and experiential platforms, exceeding revenue targets by more than 200% and contributing over $3.5 million in revenue growth. His earlier experience with Crain Communications, PHD, Showtime Networks, NBC Sports Group, and the Los Angeles Dodgers gave him broad exposure to media strategy, brand development, commercial partnerships, and audience engagement. These experiences strengthened his ability to understand diverse business models, connect creative thinking with financial performance, and adapt commercial strategies to changing consumer behaviors and market conditions.
Throughout his career, Samuel has developed expertise at the intersection of commercialization, go-to-market strategy, enterprise sales, strategic partnerships, marketing, product development, and operations. He is particularly effective in environments where organizations possess valuable technologies, products, or intellectual property but require stronger commercial strategies to unlock their potential. His approach combines market intelligence, financial awareness, cross-functional collaboration, and a practical understanding of organizational capabilities. Whether evaluating new market entry, improving pricing and distribution models, developing partnership ecosystems, or supporting acquisition-related decisions, Samuel emphasizes balancing ambitious growth objectives with responsible resource allocation and the protection of core business strengths. His experience working alongside founders, C-suite executives, investors, and board members enables him to bring both strategic perspective and firsthand operating knowledge to complex business decisions.
Beyond his corporate accomplishments, Samuel has contributed to industry conversations through published commentary, interviews, podcasts, and thought leadership. He has been featured in Muse by Clio, MG Magazine, and MediaPost, sharing perspectives on digital advertising, emerging technologies, consumer engagement, and the evolution of cannabis marketing. His podcast appearances include AdTech Unfiltered and discussions addressing marketing strategy and the challenges of evolving industries. Through his Impressions to Impact content series, he explores how programmatic advertising, data, measurement, and commercial accountability can help businesses achieve meaningful results. His industry contributions reflect a commitment to exchanging ideas, educating business leaders, and encouraging more thoughtful approaches to innovation. His professional excellence was also recognized with Horizon Media’s Rep Your Rep Award in 2017, acknowledging his exceptional client service, strategic partnership management, and dedication to delivering results.
Samuel’s academic background complements his extensive practical experience. He earned a Bachelor of Science from Boston University, where his studies focused on communications and media, and pursued additional business and digital marketing education at New York University. He also holds The Trade Desk’s Edge Academy certification in Data-Driven Planning. His educational foundation, combined with years of experience across technology, media, and commercial leadership, has shaped an adaptable perspective on business development and market evolution. He brings experience working with international markets, including Canada, and has an understanding of Italian and Hebrew. His commitment to continuous learning reinforces his belief that effective leaders must remain open to new ideas, emerging technologies, and perspectives that challenge established thinking.
Equally important to Samuel’s professional identity is his commitment to service, mentorship, and community impact. He has maintained a longstanding connection to the CJ Foundation for SIDS, an organization founded by his parents in memory of his sister, Carly Jenna. Through consulting, fundraising, and advocacy, he has supported the foundation’s mission of advancing research, education, and awareness surrounding sudden infant death syndrome. His involvement with New York Road Runners has also included serving as a marathon fundraising team captain, helping coordinate a nine-person team that raised approximately $50,000 for the foundation. These experiences reflect a deeply personal understanding of purpose-driven leadership and the importance of contributing to causes that extend beyond professional achievement. Outside of business, Samuel enjoys music, sports, travel, culinary experiences, and exploring new cultures, interests that complement his curiosity and appreciation for diverse perspectives.
At the center of Samuel’s leadership philosophy is a belief that the best decisions begin with better questions. His personal mission statement asks, “What are we missing?”—a question that guides his approach to challenging assumptions, uncovering overlooked opportunities, and helping leaders make more informed choices. He values candor over comfort, constructive disagreement over passive consensus, and relationships built through trust rather than transactions. He believes that organizations perform best when leaders encourage diverse perspectives, act with integrity, and balance financial objectives with their responsibilities to employees, customers, and stakeholders. His commitment to protecting successful business foundations while pursuing innovation reflects a disciplined approach to growth that considers both opportunity and risk.
As he expands his involvement in board and advisory opportunities, Samuel seeks to apply his commercial leadership, entrepreneurial experience, and strategic judgment to organizations navigating growth, transformation, and evolving market conditions. He is particularly interested in opportunities across technology, healthcare, and sports, while remaining open to businesses in other industries and at different stages of development. His experience with venture-backed businesses, acquisition transactions, executive leadership teams, and operational scaling positions him to contribute valuable perspectives on revenue strategy, market expansion, business performance, and enterprise value creation. He approaches the boardroom as an engaged strategic partner who asks difficult questions, respects management’s operating responsibilities, and helps leadership evaluate opportunities through a balanced lens of innovation, financial discipline, and organizational readiness.
Looking ahead, Samuel’s vision is to help build companies whose products matter, whose people continue to grow, and whose value extends beyond any individual leader. He aspires to support founders in making smarter strategic investments, mentor the next generation of business leaders, and leave organizations stronger financially, culturally, and competitively than when he joined them. His career reflects a consistent ability to recognize opportunity, unite people around shared objectives, and turn ambitious ideas into measurable outcomes. With a distinctive combination of commercial expertise, entrepreneurial perspective, acquisition experience, and values-driven leadership, Samuel Hollander brings a thoughtful and results-oriented voice to executive teams and boardrooms seeking to build sustainable businesses and create lasting value.
Character:
Samuel demonstrates integrity, accountability, and a genuine commitment to doing what is right for people, even when difficult decisions require personal conviction. His dedication to charitable causes, mentorship, ethical leadership, and long-term relationships reflects a values-driven approach that places trust and responsibility at the center of professional success.
Knowledge:
With more than two decades of experience spanning technology, advertising, healthcare-related marketing solutions, enterprise sales, strategic partnerships, and business commercialization, Samuel possesses a broad understanding of how organizations operate, compete, and scale. His firsthand involvement in business acquisitions, revenue transformation, product development, and executive decision-making equips him with the practical insight necessary to evaluate complex commercial opportunities and organizational challenges.
Strategic:
Samuel excels at identifying untapped market potential, questioning established assumptions, and translating commercial opportunities into actionable strategies that generate measurable business results. His ability to balance innovation with financial discipline, operational readiness, and long-term enterprise value makes him a valuable strategic partner to founders, executive leadership teams, and boards of directors.
Communication:
An effective communicator who brings clarity to complex business challenges and fosters productive dialogue among executives, cross-functional teams, partners, and stakeholders. Through consultative leadership, industry thought leadership, mentoring, and executive-level presentations, he demonstrates an ability to build consensus, encourage constructive debate, and align diverse perspectives around shared objectives.
