Overview

Aspire Software acquires and builds mission-critical software businesses for the long term. We are seeking a Managing Director to lead one of our flagship vertical market software businesses — a company with a strong market position, loyal customer base, and a long track record of success within the Aspire portfolio. This business is a cornerstone asset with meaningful scale and reputation in its market, now at an exciting point in its evolution with clear opportunities to expand its reach, enhance its product offering, and accelerate growth.

The Agentic MD

A truly agentic MD goes beyond adopting AI tools to fundamentally redesign how the business operates, competes, and creates value. This means building an organization where intelligent systems and human teams work together — automating routine decisions, augmenting complex ones, and enabling faster, data-driven execution across every function. An agentic MD embeds AI into the core of the product, leverages it to transform sales and marketing effectiveness, and drives operational efficiency through automation at scale. They cultivate a culture of experimentation, accountability, and continuous learning, ensuring the organization is not only using AI but evolving with it.

The Role

This is a full P&L Managing Director role with end-to-end ownership of the business. You will define and lead the company's next chapter, building on a strong foundation while unlocking new avenues for growth, innovation, and value creation. You will operate with high autonomy, supported by Aspire's long-term investment model, operational expertise, and global network.

What You'll Lead

• •Drive the next phase of growth by expanding and scaling repeatable, high-quality revenue streams, identifying new opportunities across markets, segments, and channels, and strengthening the go-to-market strategy
• •Shape the future of the product by defining and executing a compelling product vision and roadmap, enhancing the platform through innovation, integrations, and AI-driven capabilities, and ensuring alignment with evolving customer needs and industry trends
• •Deepen customer value by improving retention, satisfaction, and lifetime value, and strengthening the company's position as a mission-critical partner to its clients
• •Lead and evolve the organization by partnering with an established leadership team, assessing organizational strengths, fostering a culture of ownership and accountability, and attracting and developing talent
• •Own performance and outcomes with full accountability for revenue, EBITDA, and cash flow, driving operational excellence, scalability, and efficiency
• •Evaluate and pursue M&A, partnerships, and adjacent growth opportunities to position the business for continued vertical market leadership

What Success Looks Like

• •Accelerated, sustainable revenue growth
• •Continued strengthening of market leadership
• •A differentiated and forward-looking product strategy
• •High customer retention and satisfaction
• •A strong, aligned, and high-performing leadership team
• •Consistent expansion of profitability and enterprise value

What You Bring

• •Experience as a CEO, Managing Director, or General Manager with full P&L ownership
• •A track record of scaling and growing established software or technology businesses
• •Strong commercial instinct across sales, pricing, and go-to-market strategy
• •Ability to lead across product, operations, and finance
• •A hands-on, ownership-driven leadership style
• •Comfort operating in a high-autonomy, performance-driven environment

Why Aspire

• •Lead a flagship business with real scale and impact
• •Operate with true ownership and autonomy
• •Be backed by a company that builds for the long term
• •Access a global ecosystem of software leaders and best practices
• •Shape the future of a business that already matters in its market