Chief Operating Officer

Chief Operating Officer

  • Full-time
  • Anywhere


Our client, The Shepherd Group (TSG) is looking for a Chief Operating Officer to take their insurance and financial services brokerage to new heights! They are seeking an experienced and dynamic leader who is passionate about providing personalized and reliable insurance solutions to clients. As COO, you’ll have the opportunity to streamline TSG’s operations and drive growth, all while fostering a culture of excellence, innovation, and teamwork.

As COO, you’ll be at the forefront of TSG’s efforts to innovate and improve their services, using the latest technologies and best practices to optimize processes and enhance the customer experience. You’ll work closely with the CEO and other leaders to set ambitious goals and lead the execution of strategies to achieve them, leveraging TSG’s strengths and addressing any weaknesses. You’ll also have the opportunity to shape TSG’s culture and build out a high-performing team that aligns with the vision, mission, and values of the organization.


Founded in 2008, The Shepherd Group lives and breathes the entrepreneurial business owner lifestyle, which is why they are the top choice for Canadian businesses entrepreneurs looking for insurance solutions. TSG provides clients with a one-stop-shop for their business, personal and life & group insurance needs. With a deep understanding of the unique challenges faced by entrepreneurs and business owners, TSG offers comprehensive insurance solutions tailored to the needs of various industries.

What sets The Shepherd Group from other insurance brokers is their unwavering commitment to their clients and employees. TSG believes that by putting people first, they can create long-lasting relationships based on trust, transparency, and mutual respect. TSG is not just in the business of selling insurance, they’re in the business of protecting what matters most to their clients and helping them achieve their goals.


The successful candidate will be aligned with the core values of The Shepherd Group:


  • Always put our best foot forward.
  • Approach challenges with a positive, can-do attitude. Continuously look for solutions.
  • Take initiative to do what’s right.


  • Take personal accountability for the decisions we make and actions we take.
  • Create an environment of engaged employees who are empowered to take initiative. Communicate often and openly.


  • Use our knowledge to determine the win-win solution for our customers and the company.
  • Be agile in our approach. Use our expertise to continuously improve and adapt.
  • Take pride in our work and celebrate our achievements.


  • Be consistent in demonstrating our Purpose, Vision, Mission and Values.
  • Be counted on to fulfill one’s agreements.
  • Be accurate, responsible and accountable for all that we do.


  • Be committed to making an impact.
  • Demonstrate professionalism in all that we do.
  • Be a leader in our industry, including always operating in alignment with regulations, rules and policies.


People Management:

  • Utilize best practices and creative thinking to help drive TSG towards recognition as an employer of choice.
  • Develop a consistent training and onboarding program that aligns with the vision, mission, and values of TSG, while ensuring that new hires are set up for professional success.
  • Lead full-360 recruitment process to identify and onboard a highly engaged and talented team of operational professionals.
  • Provide leadership and direction to operational teams, fostering a culture of collaboration, continuous improvement, and high performance.
  • Drive employee engagement through eNPS feedback, team building events, and community involvement.
  • Monitor the performance of team by conducting bi-weekly 1:1 meetings with all direct reports and completing monthly performance scorecards.

Strategic Execution:

  • Support the successful execution of TSG’s strategic priorities.
  • Support TSG’s strategic partnerships, including relationships with insurers and other vendors.
  • Support and drive organic growth in both revenue and client count.
  • Manage expenses and spending to achieve annual EBITDA target.
  • Oversee performance metrics and KPIs to monitor and improve operational performance.
  • Manage and expand on TSG’s referral program.
  • Analyze data and identify areas for optimization, cost reduction, and process streamlining.
  • In conjunction with the CFO, ensure TSG has the most effective software and technology solutions for the company and client needs.

Quality Assurance/Compliance:

  • Establish and enforce policies and procedures that comply with industry regulations and best practices. Ensure that the quality of work produced and all operational activities are conducted in adherence to legal and regulatory requirements.
  • Leverage insurance vendors to develop and implement a monthly quality assurance audit that reviews, scores and provides visibility to coaching on all areas of compliance. Implement measures to protect the company’s assets, data security, and reputation.

Communication and Reporting:

  • Own all internal and external communications surrounding operations.
  • Orchestrate collaboration and knowledge sharing amongst management to create synergies and open up new opportunities.
  • Provide a weekly update to the leadership team on the operational performance of the organization.
  • Ensure that the operational structure is straightforward, with minimal layers and clearly defined and communicated responsibilities.


  • You are a seasoned professional with a minimum of 10+ years in a Senior Operations Leadership role (VP or COO). Experience in the insurance sector is highly valued.
  • You possess a Degree or Diploma in Business Administration, Finance, Accounting, or related field.
  • You have proven success in leading high-performing engaged teams and driving operational excellence.
  • You have experience working with or the ability to quickly learn broker management systems and CRM.
  • You are an expert at full-cycle recruitment and understand the importance of sourcing, hiring, and retaining top-tier talent.
  • You have a thorough understanding of financial principles, including budgeting, financial analysis, and performance metrics.
  • You are able to effectively communicate and collaborate with stakeholders, including executives, employees, clients, regulators, and external partners.
  • You can both analyze and act with equal ease. You have a strong ability to multitask, rather than being a pure analyst or thinker.
  • You anticipate and plan for changes to current organizational policies, practices, systems, etc. needed to move in new strategic directions and to ensure long-term success.
  • You have strong decision-making skills and the determination to see projects through to the end. Proven success tackling short-term goals while building towards a larger strategic vision.
  • You are an expert at engaging with people and building alliances in order to get all the information and support you need to transform business practices.



  • Salaries
  • Commissions
  • Bonus plan

Health & Wellness

  • Group benefits
  • Employee & Family Assistance Program
  • Paid Time Off
  • Flexible Work Arrangements


  • Education support
  • Professional Development
  • Clear succession paths and options

Work Environment

  • Tools and technology
  • Recognition programs
  • Volunteer Day
  • Focus on Diversity & Inclusion
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