Head of Business Development

As our Head of Business Development, reporting directly to the CRO and Co-Founder, you will lead and scale Riverside's global Business Development organization. You will own outbound pipeline generation across SMB, Mid-Market, and Enterprise segments, while also helping Riverside turn its strong product-led growth motion into a more powerful source of sales-led opportunities.

This is a highly visible leadership role with meaningful impact on revenue, go-to-market strategy, sales productivity, and company execution. You will lead four Business Development teams across Toronto and Israel, managing both frontline managers and Business Development Representatives. Your mandate will be to scale an already successful outbound engine, improve operational excellence, increase pipeline quality, and create stronger connections between PLG signals and SLG pipeline creation.

We are looking for a leader who combines strong people leadership, sharp operational judgment, and a modern AI-first approach to building outbound teams. The right person has experience managing managers, operating across geographies, hiring and developing top talent, and using data, systems, AI, and product usage signals to improve productivity and performance.

What will your day-to-day look like?
• Lead, mentor, and develop Riverside's global Business Development organization across multiple teams, regions, managers, and individual contributors.
• Own outbound pipeline generation across SMB, Mid-Market, and Enterprise segments, with clear accountability for pipeline creation, pipeline quality, and revenue impact.
• Partner with Sales, Marketing, Revenue Operations, Data, and Product to identify high-intent PLG signals and convert them into qualified sales-led opportunities.
• Build and improve motions that turn product usage, team expansion, account engagement, and customer behavior into prioritized BDR workflows and SLG pipeline.
• Scale and improve Riverside's existing BDR function by strengthening processes, improving execution, and increasing productivity across the organization.
• Partner closely with the CRO, Sales leadership, Marketing, Revenue Operations, and other cross-functional stakeholders to align outbound and PLG-assisted pipeline strategy with company growth priorities.
• Build and execute hiring plans that support continued growth, including attracting, selecting, onboarding, and developing top Business Development talent.
• Coach and develop managers to build high-performing teams with strong accountability, clear performance standards, and meaningful career progression.
• Use AI tools and automation to improve prospecting, account research, outreach personalization, coaching, workflow efficiency, forecasting, and operational decision-making.
• Define and monitor the right performance metrics, using data to identify gaps, improve conversion, raise productivity, and increase overall business impact.
• Improve the quality and consistency of outbound execution across regions, including messaging, targeting, prioritization, follow-up, and meeting quality.
• Build a culture of high standards, ownership, continuous improvement, experimentation, and strong execution across the Business Development function.

What you bring to the table
• 3+ years of leadership experience in Business Development, Sales Development, or outbound sales leadership roles within SaaS.
• Proven experience managing managers and leading multi-layered teams at scale.
• Track record of growing and optimizing outbound Business Development organizations with measurable pipeline and revenue impact.
• Experience building pipeline motions that combine outbound execution with PLG signals, product usage data, intent data, or customer engagement insights.
• Experience leading distributed or international teams across multiple geographies.
• Strong hiring and talent development experience, with demonstrated success building high-performing teams and future leaders.
• Deep understanding of outbound go-to-market strategy across SMB, Mid-Market, and Enterprise customer segments.
• Strong operational discipline, with the ability to use data, systems, and clear processes to drive better decision-making and team performance.
• Hands-on experience using AI tools to improve prospecting, workflows, coaching, productivity, and team execution.
• Strong executive presence and the ability to influence senior stakeholders across Sales, Marketing, Revenue Operations, Product, and leadership.
• High ownership, strong judgment, and the ability to operate in a fast-moving, high-growth environment.
• Clear communication, strong coaching skills, and a direct leadership style that raises the bar for the entire team.

Additional information
• This role is based in the Greater Toronto Area, with an expectation to work from our Toronto office approximately 1-2 times per month.