Drive outbound engagement at a SaaS startup and shape the future of intelligent customer solutions. Conduct high-volume outbound outreach to identify and engage prospective clients. Craft compelling messaging tailored to verticals using advanced personalization tools. Utilize AI prospecting and CRM platforms to manage pipeline and improve conversion rates. Partner with account executives to develop territory strategies.

Drive new, upsell, and cross-sell sales of Caseware’s product suite, focusing on small and medium-sized clients within the US market. The role focuses on sales within the firm market segment, primarily selling our OnPoint suite of products to small firms and sole proprietors and is a 50/50 split between inbound & outbound activities. We are going through a build-up of our Sales organization, and you will be a founding member of the future of Sales Operations at Caseware.

This high-impact Director of Sales will lead, coach, and scale a world-class team of Account Executives (AEs) focused on driving new business growth across defined territories. The Director will champion a high-performance, high-accountability culture centered on innovation, execution, and results. They will directly drive Trustwell’s new logo revenue objectives quarter after quarter.