Head of Sales

Head of Sales Join to apply for the Head of Sales role at INSAUGA Inc., a leading digital-only media company in Canada with a hyper‑local focus in Ontario. With 15 million monthly page views and 600 k 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. 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 – recruiting, onboarding, training, goal‑setting and ongoing performance management to ensure the team reaches quotas. Identify skill or knowledge gaps within the team and implement targeted coaching, training programs and development initiatives. Oversee month‑end and year‑end sales processes – accurate reporting, pipeline hygiene and timely close of all revenue activities. Prepare and present detailed sales, revenue and expense reports, including forecasts, insights and recommendations for senior leadership. Monitor market trends, competitive activity and emerging opportunities; develop strategies to keep the company highly competitive and well‑positioned for growth. Ensure CRM excellence – maintain accurate, up‑to‑date data in HubSpot and reinforce 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 organisations. Proven success as a sales executive with a measurable track record of selling digital advertising solutions (display, sponsored content, social media, 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 – and strong working knowledge of Google Workspace and Microsoft Office. Deep understanding of social and digital ecosystems (Facebook, Instagram, TikTok, YouTube, 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; ability to influence internal and external stakeholders. Strong business acumen and leadership capability with 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 – a strong asset. Bachelor’s degree in Business, Marketing, Sales or a related field (or equivalent experience). Why Join INsauga? Collaborative, creative and impactful culture – a growth mindset with real opportunities to make a difference. Comprehensive benefits package: dental and vision care, extended health coverage, employee assistance program, and flexible paid time off including vacation. Flexible work arrangements and ability to work from home. Engaging company culture with in‑person meetings, social events and team‑building activities. Opportunities for career growth, professional development and skills training. Wellness programmes (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 Job reference: J‑18808‑Ljbffr #J-18808-Ljbffr