Employment type: full time POSITION: Head of Sales & Business Development LOCATION: Toronto, Ontario POSITION DETAILS: Full Time, Permanent REPORTS TO: Managing Director DIRECT REPORTS: One (total team size of four) WEBSITE: https://www.pinktrianglepress.com/ THE ORGANIZATION Since 1971, Pink Triangle Press has evolved from a pioneering gay liberation newspaper, named by Masthead Magazines as one of “Canada’s 20 most influential magazines of all time”, into one of the world’s longest-running 2SLGBTQIA+ media and advocacy organizations. Today, we operate a diverse, highly engaged ecosystem spanning journalism ( Xtra Magazine ), travel, health, dating, and national advocacy initiatives. Our aim is to inspire LGBTQ2S+ communities to pursue a future where everyone is free to celebrate who they are. We inspire bold ideas and Set Love Free. We are proudly amongst the winners of both the GTA’s Top Employers and Canada’s Top Small and Medium Employers awards for 2026. THE OPPORTUNITY Driven by deep community trust, groundbreaking research, and a mission to champion equity and celebrate queer and trans lives, we offer an uncommonly broad foundation for growth. For a sales leader, this means an extraordinary platform to leverage trusted digital properties, tap into dynamic audiences across Canada and internationally, and drive meaningful revenue for an organization with clear vision and lasting impact. The Head of Sales & Business Development ensures products and services resonate with audiences, clients, and funders, resulting in growing awareness, engagement, revenue, and profitability. They will directly drive PTP’s commercial sustainability through hands-on sales, sponsorship acquisition, and strategic partnership development. RESPONSIBILITIES Business Development Build and execute a business development strategy to identify, evaluate, and pursue revenue opportunities. Bring in sponsors, commercial partners, and strategic alliances to meet revenue targets. Evaluate and test business opportunities and models for growth and sustainability. Bring new Products and services to market expeditiously. Utilize internal and external data to continuously refine commercial efforts. Ensure all new initiatives are vetted for revenue potential and net margin. Sales & Revenue Strategy Drive PTP’s Sales strategy by directly closing deals, maximizing revenue across properties, and nurturing key relationships. Identify and execute B2B revenue and funding opportunities across all properties, in collaboration with the Head of Dating Businesses, Senior Manager, Brand and Marketing Communications, and Advertising & Partnerships Manager. Personally build, manage, and scale sponsorship and business partner relationships. Manage Sales and Sponsorship personnel, motivate staff to meet targets and close deals. Own and hit/exceed annual individual and organizational sales targets. Develop and execute hands-on sales plans to expand the customer and partner base. Identify and support applications for relevant grants and institutional funding opportunities. Articulate the PTP commercial value proposition through high-impact proposals and presentations. Authority Develop annual sales and business development strategies, KPIs, and revenue goals. Maximize revenue across B2B, B2C, sponsorships, and other funding sources (e.g., grants, charitable support). Manage the sales and business development operational budget. Initiate and negotiate commercial terms within established internal controls. CANDIDATE QUALIFICATIONS A minimum of 8 to 10 years’ experience of individual contribution and senior-level success in sales, sponsorship acquisition, and business development. A demonstrated track record is valued over formal credentials. Proven history of hitting and exceeding revenue targets and closing high-value commercial deals. Experience in B2B sales pipelines, sponsorship models, and strategic partnership structures. Hands-on sales capability in prospecting, outreach, pitching, negotiating, and closing B2B sales and sponsorships. Ability to build creative, high-value sponsorship packages. Deep knowledge of LGBTQ2S+ communities, market dynamics, and audience needs. Brings business savvy and ability to manage multi-stakeholder relationships. Exceptional relationship-building skills with external clients, partners, and funders. Skilled in crafting compelling sales presentations, proposals, and narrative pitches. High credibility when representing PTP at industry functions, trade shows, or client meetings. Expands networks to increase awareness, open possibilities, and secure high-value partnerships. Strong negotiation skills with a track record of securing favourable terms. Ability to prepare concise business cases, evaluate ROI, and bring revenue initiatives to market. Capable of detecting market trends, competitor movements, and emerging opportunities. High financial acumen, business comprehension, and capability in revenue modelling. A strategic thinker with a pragmatic, ‘roll up the sleeves’ executive focus. Ability to assess resource needs (time, budget, ROI) and execute commercial strategies independently. Leverages metrics and data to drive results, optimize sales pipelines, and ensure accountability. Comprehensive understanding of the political, regulatory, and governance environment in which PTP operates. Open to utilizing AI and technology tools to streamline outreach and sales workflow. CANDIDATE ATTRIBUTES Fosters a deep appreciation for PTP’s mission, enthusiasm for advancing its work, sex-positivity, and commitment to LGBTQ+ communities. Strives for excellence and continuously tests, evaluates, course-corrects, and learns. Action-oriented, open to new ideas, risk-tolerant, and adaptable. Identifies and resolves issues quickly with practical solutions. Ability to work seamlessly across departments as an individual contributor to achieve broader organizational goals. Driven to make an impact, expand commercial reach, and grow revenue. A natural netw