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Open nowPosted 53 days ago

Managing Director

Workable (global search)108,016 open roles

Where
Canada
Work mode
Remote
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Your applicationOpen nowManaging DirectorWorkable (global search) · Canada

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7.9% of postings close within 7 days. Measured by our own scanner across the market. Workable (global search) postings stay open a median of 7 days.

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  2. 3.6%3 days
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  4. 14.9%14 days
  5. 34.0%30 days
This job: posted 53 days ago

Workable (global search) median: 7 days open

The posting

Managing Director

Remote — Canada or United States | Full-time | Reports to: Managing Partner

About Edelweiss Software Group

Edelweiss Software Group is an operating group of Valsoft Corporation, serving as a permanent basecamp for vertical market software companies. Our philosophy is simple: your company leads; we support the ascent. With a buy-and-hold-forever approach, Edelweiss preserves each company's brand and provides the steady guidance, capital, and resources needed to keep both products and people moving upward. We form long-term strategic alliances with existing management teams — we don't buy to sell — placing a premium on the well-being of customers and employees over short-term goals.

The Role

We are seeking an entrepreneurial and operationally minded Managing Director to lead one of our software businesses. Reporting directly to the Managing Partner, you will own the P&L, set strategic direction, and drive sustained, profitable growth across the product portfolio.

This is a hands-on operator role for a leader who can build as much as run. The business is at an exciting inflection point, with a stable core and a new generation of products moving toward market. You will define and execute the strategy for its next phase — evolving the operating model, sharpening the go-to-market engine, and bringing new products successfully to market — while building a transparent, high-performing, customer-obsessed organization. You will operate with high autonomy, supported by Valsoft's long-term investment model, operational expertise, and global network.

What You'll Lead

• Drive the next phase of growth — Expand repeatable, high-quality revenue; refine cross-product go-to-market; and identify new opportunities across markets, segments, and channels.

• Steer the product portfolio — Refine clear, market-aligned product roadmaps, bring the next generation of products to market and toward self-sustaining economics, and leverage emerging tools (including AI) to enhance the platform.

• Evolve the operating model — Move toward business-unit-level ownership and accountability, with the transparency, discipline, and incentives to scale while improving E2E operational efficiency with the use of AI

• Deepen customer value — Improve retention, satisfaction, and lifetime value, and embed a culture of customer-led innovation.

• Own performance and outcomes — Take full accountability for revenue, EBITDA, and cash flow, with disciplined capital allocation and predictable financial performance.

• Lead and grow the organization — Build and develop a high-performing team and a culture of ownership, accountability, continuous improvement, with a customer-first mindset.

Candidate Profile

Experience

• Proven experience as a CEO, Managing Director, COO, VP or General Manager with full P&L ownership of a software or technology business.

• P&L scale: Prior P&L accountability of $5M or more.

• Team leadership: Experience leading and developing a team of 10 or more.

• New-product track record: Has brought new products to market and successfully scaled them.

• Track record of scaling and growing established software businesses and of transforming a business.

• Strong commercial instinct across sales, pricing, and go-to-market strategy, including cross-sell and market penetration.

• Ability to lead across product, operations, and finance, with sound financial acumen (P&L management, budgeting, forecasting).

• Comfort with emerging technologies, including AI.

• Bachelor's degree in business, finance, engineering, economics, or a related field; an MBA or advanced degree is a strong asset.

Personal characteristics

• Empathetic leader:A strong ability to influence others, and an empathetic, active listener.

• Entrepreneurial spirit — results-oriented, driven, proactive, and a team player.

• Both strategic and hands-on, with the ability to translate vision into actionable plans and drive results.

• A high degree of accountability and ownership.

• Ability to thrive in a fast-paced, dynamic environment and adapt to change with agility.

• A people-centric leader who leads with humility, empathy, and sound judgment.

Why This Opportunity Stands Out

• A platform for growth — Lead an established, market-leading business at a genuine inflection point — with the core stabilized and a new product generation ready to scale.

• True ownership — Run the business with full autonomy and accountability, empowered to make decisions and drive outcomes.

• Long-term backing — Valsoft's buy-and-hold-forever model means you build enduring value rather than managing toward an exit.

• A proven operating model — Access Valsoft's playbooks, capital, and global network of experienced software operators while retaining independence in execution.

• Flexibility — Fully remote, based anywhere in Canada or the United States.

#EdelweissSoftware

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