Group Managing Director

This is a fully remote position, open to applicants in United States.

📋 Description

• Oversee two established vertical software companies as a unified leader with dual P&Ls.

• Take responsibility for the annual budget and organic growth objectives for both entities.

• Manage combined revenue, develop the sales pipeline, and meet a quota until a suitable successor is appointed.

• Create a repeatable go-to-market strategy.

• Assume control of sales, renewals, and public tender processes in one business as its founder transitions to an advisory role.

• Evaluate the feasibility of jointly selling to the two customer bases.

• Manage gross and net revenue retention, analyze customer churn, address underlying issues, and implement save strategies for at-risk accounts.

• Cultivate relationships with the top 20 accounts across both businesses.

• Oversee both P&Ls, managing allocations for spending, product, sales, service, and administration.

• Handle working capital, collections, and deferred revenue.

• Assess, retain, and nurture teams; address performance and organizational requirements.

• Establish a distinct leadership framework across both companies.

• Develop product roadmaps aligned with revenue targets.

• Determine the connection between the two products and evaluate customer value.

⛳️ Requirements

• Proven P&L ownership of a software business generating approximately $3M–$15M in revenue.

• Experience selling to government entities, the public sector, or regulated healthcare purchasers.

• Familiarity with procurement processes, RFPs, tenders, and grant cycles.

• Willingness and capability to engage in direct sales activities, rather than merely overseeing sales teams.

• Proficiency in analyzing a P&L by function and reallocating budget without requiring a CFO.

• Experience transitioning from a founder or a long-serving leader while maintaining customer relationships and team cohesion.

• Willingness to travel approximately one week each month across two locations.

• Preferred: direct experience in public health, community health, human services, or healthcare IT.

• Preferred: experience in recurring-revenue businesses where renewals and retention are critical for success.

• Preferred: background in managing two business units, brands, or product lines concurrently.

• Preferred: experience in a permanent-capital, holding company, or family office environment.

• Not suitable for first-time General Managers, executives reliant on large teams, venture-funded scaling operators, or candidates intending to merge the two brands within the first year.

🏝️ Benefits

• Comprehensive health and wellness benefits.

• Competitive salary with performance-based incentives.

• Opportunities for professional development and career advancement.

• Flexible work schedule and remote work options.

• Engaging work environment with a focus on innovation.