Bennett Deady

Background

About Bennett Deady

I’m a sales professional who does best in fast-paced, high-performance environments where curiosity, strong communication, and real problem-solving move things forward. I’ve built my career in the mid-market and emerging enterprise space, owning the full cycle from deep discovery and multi-threaded conversations, to complex negotiations that drive measurable results and value.Currently, I’m a Sr. Mid-Market AE at ImageTrend, operating entirely in an outbound focused, greenfield territory within the public safety and healthcare tech space. My focus is on building pipeline from scratch, increasing market presence, and driving new business through disciplined outbound, relationship-building, and strategic account development. I’m highly motivated by the opportunity to create long-term value in a complex market with real-world application.Prior to ImageTrend, I helped organizations streamline hiring strategies with AI-powered recruiting software, partnering directly with HR and business executives to optimize workflows and efficiency. My role covered the full spectrum, from high-volume qualifications, to tailored demos, and cross-functional collaboration with product, legal, and implementation teams. At Workable, I consistently exceeded quota (125–175%) by staying sharp in discovery and always driving deliberate next steps.Before that, I co-founded and led sales at FROO, taking a product from concept to revenue. We launched a guided, productivity tool for student success and partnered with institutions like Boston College, Babson, USC, and Stanford. That experience deepened my passion for building from scratch and finding product-market fit.Earlier, I served as a Founding Account Executive at OnDemand Storage, helping launch and grow a new B2B services venture from the ground up. I sourced and closed partnerships nationwide, developed go-to-market strategy, and led expansion into 15 cities. Earlier roles at Toast and Lola.com gave me strong foundational SaaS skills and taught me how to execute with precision in both high-velocity and enterprise-level sales environments.