Head of Sales

Join to apply for the Head of Sales role at INSAUGA Inc. Get AI-powered advice on this job and more exclusive features. INSAUGA.com is a leading digital-only media company in Canada, with a hyper-local focus in Ontario. With 15 million monthly page views on our website and 600K social media followers, we provide readers with engaging local content spanning food, real estate, lifestyle, travel, breaking news, and more. About you We are seeking a full-time Head of Sales and Business Development in Mississauga, ON to build, grow and lead our sales department. This is an exciting opportunity for someone who is passionate about the digital space, able to wear multiple hats and eager to join a growing team. In this leadership role, you will oversee sales and business development activities, manage a high-performing sales team, and drive revenue growth for the Company. Responsibilities Develop and execute a comprehensive sales strategy to expand insauga.com’s customer base, accelerate revenue growth, and enhance regional market presence. Lead, mentor, and manage the sales team , including responsibility for recruiting, onboarding, training, goal-setting, and ongoing performance management, ensuring your team reaches their quotas. Identify skill or knowledge gaps within the team and implement targeted coaching, training programs, and development initiatives to strengthen capabilities. Oversee month-end and year-end sales processes , ensuring accurate reporting, pipeline hygiene, and timely close of all revenue-related activities. Prepare and present detailed sales, revenue, and expense reports , including accurate forecasts, insights, and recommendations for senior leadership. Monitor market trends, competitive activity, and emerging opportunities , and develop strategies to keep the company highly competitive and well-positioned for growth. Ensure CRM excellence , maintaining accurate and up-to-date data in HubSpot and reinforcing consistent usage standards across the team. Develop dashboards and performance reports using CRM tools and other data sources to track KPIs, analyze team performance, and support data-driven decision-making. Requirements Minimum 5 years of progressive experience in sales leadership , preferably within high-growth or digital-first organizations. Proven success as a sales executive , with a measurable track record of selling digital advertising solutions—including display, sponsored content, social media, and video—while consistently meeting or surpassing revenue targets. Background in digital publishing, digital media, or advertising sales (highly preferred). Proficiency in CRM platforms , ideally HubSpot, along with strong working knowledge of Google Workspace and Microsoft Office. Deep understanding of social and digital ecosystems , including Facebook, Instagram, TikTok, YouTube, and LinkedIn, and how brands leverage these channels for performance and brand marketing. Demonstrated ability to lead the full sales cycle — from strategic planning and pipeline development to negotiation and deal closure. Exceptional communication, relationship-building, and presentation skills , with the ability to influence both internal and external stakeholders. Strong business acumen and leadership capability , including experience coaching and developing high-performing sales teams. Willingness to travel alongside sales executives for client meetings, industry events, and partnership opportunities. Based in the Greater Toronto Area , with strong knowledge of the local media, agency, and brand landscape. Experience working with media agencies or in media planning is a strong asset. Bachelor’s degree in Business, Marketing, Sales, or a related field (or equivalent experience). Why Join INsauga? Collaborative. Creative. Impactful. INsauga combines a growth mindset with real opportunities to make a difference—where ideas are celebrated and teamwork drives success. Comprehensive benefits package: dental and vision care, extended health coverage, employee assistance program (EAP), and flexible paid time off, including vacation time Flexible work arrangements and ability to work home Engaging company culture with in-person meetings, social events, and team-building activities Opportunities for career growth, professional development, and skills training Wellness programs (gym memberships, wellness stipends, mental health initiatives) We thank all candidates for applying, however, only successful candidates will be contacted. Please upload your resume as a PDF file. Seniority level Director Employment type Full-time Job function Sales and Business Development Industries Online Media Referrals increase your chances of interviewing at INSAUGA Inc. by 2x Get notified about new Head of Sales jobs in Mississauga, Ontario, Canada . #J-18808-Ljbffr