Justin Gelbman is a Managing Director of investments at Oppenheimer & Co. Inc. and a founding member of The Sharpe Group, where he works with business owners, executives, and families on long-term financial planning. Based in Princeton, New Jersey, he holds the Certified Financial Planner designation along with multiple securities and insurance licenses, enabling him to address complex planning needs from a comprehensive perspective. His work frequently involves guiding closely held business owners through issues that affect continuity, leadership transitions, and long-term value preservation. In the context of small business succession, Justin Gelbman’s experience aligns with the need for disciplined planning, clear communication, and operational readiness. By combining collaborative planning with ongoing analysis, his approach reflects the importance of preparing organizations to navigate leadership change while protecting stakeholders, employees, and the broader legacy of the business.
Ensuring a Small Business Survives Succession
A February 2024 Oppenheimer article recommended strategies for small business owners to ensure business continuity as part of legacy planning. These strategies provide business owners with a step-by-step guide to ensuring their company transitions to new leadership smoothly, including focusing on talent acquisition, communication, and operational strategies.
Experts recommend that company heads plan for succession three to five years before it occurs, allowing them time to find and install effective leaders. According to an April 2025 Harvard Business Review article, business owners should prioritize investing in leadership, such as using AI-powered tools to research executive talent pools, identify top skills and leadership experiences, and track where other companies are investing. Other factors that small business owners might research include the profiles and qualifications of prospective leaders and how they align with the company’s present and future needs.
Research should also focus on retaining current leaders by identifying those most likely to leave. Using AI, businesses can determine which external and internal factors are most likely to influence a leader’s decision to leave, such as market demand, company performance, and the timing of the leader’s supervisor’s appointment. This data equips small businesses with strategies to incentivize leaders to remain with the company.
Company leaders should seek talent that increases the likelihood of a successful transition, including making critical external hires and strengthening existing leadership. It creates a succession pool of experts in specific areas, such as customer experience, supply chain, or AI, and expands the expertise of current leaders.
Additionally, the Oppenheimer article encouraged business leaders to keep employees, customers, and family members in the loop throughout the entire process. Leaders should build a communications infrastructure that easily disseminates information throughout the organization and makes it accessible to everyone.
The company’s communications infrastructure should include technologies that are somewhat impervious to disruptions. These platforms are highly reliable and feature enterprise-level security. They should have built-in compliance and accessibility features that align with industry standards and regulations. Furthermore, the communications platform should be able to grow easily as the business expands.
This communication platform should be multichannel, including live and on-demand channels accessed online through desktop and mobile devices. Employees, management, family members, and other stakeholders should be able to access stakeholder information, compliance training, and leadership town halls in multiple formats. An October 2025 Forbes article also recommends creating pre-approved messaging for email, social media, the website, and other employee channels in case of a disruption. The proactive approach to communication reduces downtime and builds trust among stakeholders.
Other strategies for creating a robust communications platform are using key active and passive data to make improvements and adopting a people-first approach. Active data, such as registration information, and passive data, such as session attendance, provide analytics that leaders can use to understand whether their messaging was effective. Also, ensuring the platform is accessible and that messages reach everyone in the organization engenders trust, expands reach, and builds connections among stakeholders.
Finally, small business owners must also leverage technology to strengthen operational efficiency. These improvements begin with auditing and streamlining operational processes to ensure that everyone within the organization is working from the same information. Moreover, it enables business leaders to reduce redundancies and errors while also ensuring that the critical processes are not the responsibility of a single person.
About Justin Gelbman
Justin Gelbman is a Managing Director of investments at Oppenheimer & Co. Inc. and a founding member of The Sharpe Group. He works with affluent individuals, families, and business owners on comprehensive financial planning and wealth management strategies. Holding the Certified Financial Planner designation, along with multiple securities and insurance licenses, he brings a structured and collaborative approach to addressing complex planning considerations. His professional background includes a business degree from the University of Maryland and active involvement in nonprofit and professional development initiatives.
