Senior Director

Company Overview

FlyCap Succession Capital is headed by entrepreneur Richard Gotlieb and is dedicated to acquiring and running one small to midsize business. Supported by a network of high-net-worth entrepreneurs, the firm draws on extensive operating and growth experience across a range of small and mid-market businesses. Rather than pursuing the typical private equity playbook, the company is centered on long-term ownership, responsible stewardship, and building lasting value. Its goal is to protect and strengthen the reputation of the acquired business while encouraging steady, sustainable expansion that benefits employees, partners, and customers over time.

Role Summary

The Senior Director will be a key leader in the process of sourcing, assessing, and helping oversee the acquisition and ongoing management of a small to midsize company. The role involves guiding strategic direction, monitoring performance, and supporting operational initiatives, while also developing trusted relationships with both internal teams and external stakeholders. Working closely with the leadership group, this person will contribute to investment decisions, evaluate risk, and shape value creation plans, while building systems that promote durable growth and employee development. This is a full-time remote position with occasional travel to meet partners, target businesses, and other stakeholders.

Key Responsibilities

• Lead strategic planning and help guide the long-term direction of the business.
• Track business performance and support initiatives that improve operations.
• Work with leadership on acquisition analysis, investment choices, and risk review.
• Develop and refine value-creation plans focused on sustainable growth.
• Build and maintain strong relationships with founders, management teams, investors, and external partners.
• Create processes and operating rhythms that support consistency and workforce development.
• Contribute to succession planning and founder-transition discussions where relevant.
• Travel periodically as required to meet stakeholders and evaluate opportunities.

Candidate Profile

The ideal candidate brings leadership experience in small to midsize businesses, ideally with accountability for strategy, operations, or P&L ownership. A solid background in corporate finance, investment evaluation, or transaction support is important, along with the ability to judge business performance and identify growth opportunities. Candidates should have a track record of introducing operational improvements, performance measures, and scalable processes. Strong relationship management, communication, negotiation, and decision-making skills are essential, as is the ability to work independently in a lean, entrepreneurial, remote environment. Experience with succession planning, founder transitions, or stewardship-oriented investing is a strong advantage. A bachelor’s degree in Business, Finance, Economics, or a related discipline is required; an MBA or similar advanced qualification, or equivalent experience, is considered a plus.

Additional Information

This is a remote, full-time role based in the United States. The position may involve occasional travel. The source provided no salary, stipend, or vacancy count information.