Group Leader I CEO

Cora Group, Inc.Cora Group, Inc.·Remote(Canada)
Other
Excel

WFA Digital Insight

As the demand for seasoned leaders in the software industry continues to rise, with a 25% increase in executive roles over the past year, companies like Cora Group, Inc. are looking for exceptional talent to spearhead their growth. The role of a Group Leader is particularly intriguing in today's remote job market, requiring a unique blend of strategic vision, operational acumen, and the ability to foster a culture of innovation. With the software industry's trend towards decentralization and AI-driven solutions, candidates with experience in scaling businesses, managing P&L, and guiding AI/automation initiatives will be in high demand. Before applying, candidates should be aware of the importance of balancing operational discipline with entrepreneurial freedom and the need for outstanding communication skills to succeed in this role.

Job Description

About the Role

The Group Leader role at Cora Group, Inc. is a pivotal position that oversees a portfolio of 5-7 business units, driving growth, operational excellence, and product innovation across the group. This mandate requires a seasoned leader who can coach Presidents (Business Unit Leaders), introduce best practices, and support diligence and integration for new acquisitions. The role also involves guiding leaders in identifying practical AI/ML applications that strengthen product value or internal efficiency, ensuring AI use remains realistic and business-driven.

As a Group Leader, you will be responsible for defining long-term growth plans, operational KPIs, and innovation opportunities for your group. You will also mentor business unit leaders and their teams, enabling best practices, promoting cross-unit knowledge sharing, and fostering a high-performing culture. Your expertise in managing to P&L and experience in scaling businesses will be essential in driving recurring revenue growth, profitability, churn/net retention, customer satisfaction, implementation velocity, and cost-to-serve.

What You Will Do

  • Develop and execute long-term growth plans for the group, aligning with corporate goals
  • Define and track operational KPIs for the group, ensuring data-driven decision-making
  • Identify and prioritize innovation opportunities, including AI/ML applications
  • Mentor and coach business unit leaders, promoting best practices and knowledge sharing
  • Lead acquisition integration, acting as Integration Manager for newly acquired entities
  • Oversee commercial, operational, and back-office assimilation into the Cora model
  • Highlight integration opportunities where AI/automation can streamline processes
  • Lead and support product innovation, evaluating enhancements to product strategy and customer experience
  • Analyze vertical markets, deep-diving into market dynamics, competitive landscape, win/loss reasons, pricing optimization, and positioning
  • Cascade key metrics across business units, aligning targets with corporate goals and reviewing progress via weekly, monthly, and quarterly reporting
  • Promote data-driven decision-making, leading financial reporting and forecasting, identifying efficiencies, and challenging underperforming units

What We Are Looking For

  • 10+ years of leadership experience in the software industry, ideally in vertical SaaS
  • Proven record of scaling multiple businesses, both organically and through M&A integration
  • Strong leadership and people development capability
  • Financial acumen with experience managing to P&L
  • Comfortable in a fast-changing, decentralized environment with a bias for execution
  • Outstanding communication and stakeholder management skills
  • Bachelor’s degree required; MBA or relevant graduate education preferred
  • Experience guiding teams in identifying or evaluating AI/automation opportunities
  • Proficiency in Excel and experience with analytics or automation tools

Nice to Have

  • Experience with AI/ML applications in a business setting
  • Knowledge of vertical market software companies and industry-specific segments
  • Familiarity with Constellation Software Inc.’s philosophy and culture
  • Entrepreneurial mindset and adaptability in a rapidly changing environment

Benefits and Perks

  • Competitive base salary and performance-based bonus
  • Long-term incentive opportunities reflecting Constellation’s philosophy
  • Flexible work options and comprehensive benefits
  • Strong career path opportunities and professional development
  • Access to a network of experienced leaders and professionals in the software industry
  • Opportunity to work with a diverse portfolio of business units and contribute to their growth and success

How to Stand Out

  • Utilize your experience with Excel to demonstrate your ability to manage and analyze data, a crucial skill for this role.
  • Highlight any experience you have with AI/ML applications in a business setting, as this is a desirable skill for the Group Leader position.
  • Be prepared to discuss your approach to scaling businesses and driving growth, providing specific examples from your past experience.
  • Show that you have done your research on Cora Group, Inc. and Constellation Software Inc., demonstrating your understanding of their philosophy and culture.
  • Be ready to address how you balance operational discipline with entrepreneurial freedom, a key aspect of this role.
  • Ensure your resume and cover letter are tailored to the job description, emphasizing your leadership experience, financial acumen, and ability to drive innovation.

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