Chief of Staff with Bill Gosling Outsourcing

Company: Bill Gosling Outsourcing
Industry: Business Solutions
Location: Canada Newmarket ON
Position Type: Full Time
Workplace Model: Hybrid On Site
Experience Level: 11 - 15 years
Reports to: President


Bill Gosling Outsourcing provides business solutions to their clients with various types of services including Customer Service, Accounts Receivable Management, Customer Sales, Contact Centre Technology, and Business Process Outsourcing. With over 60 years in the call centre industry, Bill Gosling has the technology and resources to help their clients get their brand where it needs to be and grow their business. Learn more at


The Chief of Staff (COS) will fulfill a dynamic and multi-faceted role at Bill Gosling Outsourcing. As the right-hand employee to the President, the COS will coordinate strategic projects across the organization’s key business functions, working with sales, operations, finance, information technology, human resources, and compliance function heads to achieve organizational goals. The role will present the opportunity to operate at both a strategic and tactical level across the organization, overseeing and executing on the Company’s highest priority initiatives.

As the organization scales organically and through acquisitions, the COS will be expected to take on additional responsibility, leading growth initiatives and integration efforts. The COS will undertake projects outside of the current President’s bandwidth and will be tasked with giving the President more insight across the entire organization.


The Chief of Staff’s responsibilities will encompass three primary areas:

    Facilitate cross-functional integration

  • Helping the President operate as the organizational “glue” overseeing each of the Company’s business functions and having the vision to ensure complex, cross-functional initiatives propel the organization in the same direction. The COS will connect the dots across business functions, ensuring executive team leads are working in concert to achieve the organization’s strategic goals
  • Build relationships with employees across the organization, understanding each team’s priorities, challenges, and opportunities
  • Assisting the Company’s Project Management Office (PMO) in both tackling discrete projects and overseeing strategic initiatives included in the project list to completion

    Deliver results on behalf of the leadership team

  • Managing the organization’s Entrepreneurial Operating System (EOS) and Vision/Traction Organizer (VTO) by facilitating the development of Company and Individual Rocks and promoting accountability across the Executive Team to achieve stated quarterly and annual goals
  • Fostering an environment of transparency and collaboration across the organization; the COS will be a resource to executive team members to remove obstacles preventing progress on strategic initiatives
  • Participating in acquisition diligence and integration

    Ensure President’s highest and best use of time

  • Identify issues as they emerge and take proactive steps to resolve them
  • Providing thought partnership to the President, acting as a sounding board for new ideas, strategies, and initiatives
  • Identifying operational weaknesses and helping improve or innovate new processes
  • Responding quickly and effectively to problems and issues that arise within the organization


  • 12-15 years of work experience
  • BA/BS required; MBA preferred
  • Exceptional verbal and written communication skills with experience communicating effectively at an executive level
  • Strong project management skills with experience managing complex cross-functional projects, including developing, coordinating, and communicating project plans and deliverables in an effective manner
  • Well-versed in financial analysis, technology, data analytics, operations, and acquisition integration
  • Experience in tech-enabled organizations, preferred
  • Ability to work with a range of stakeholders from agents to the Board of Directors
  • Ability to operate in a fast-paced, entrepreneurial environment
  • Self-starter with a strong sense of urgency and ability to see tasks through completion
  • Willingness to travel internationally to the Company’s facilities in Canada, the US, the UK, the Philippines, and Costa Rica as required
  • Vaccinated for COVID-19


  • Interested candidates can apply below.


  • Competitive salary
  • Health & Dental benefits available after an initial waiting period
  • Amazing work culture where you can learn and grow
  • Hybrid office / home flex


Bill Gosling Outsourcing is committed to ensuring equal access and participation for people with disabilities. People with disabilities will be treated in a way that allows them to maintain their dignity and independence. Bill Gosling believes in integration and is committed to meeting the needs of people with disabilities in a timely manner. Bill Gosling does so by removing and preventing barriers to accessibility and by meeting accessibility requirements under Ontario’s accessibility laws.

Accommodations are available on request for candidates taking part in all aspects of the selection process.