Kyle James

Director & Principal Analyst

Sort Research

Kyle is a seasoned technology problem solver and product management leader with over two decades of experience. He has founded two successful startups, nuCloud and .eduGuru, both of which exited, and was among the earliest team members at HubSpot (NASDAQ:HUBS) and OneScreen.ai. Throughout his career, Kyle has been instrumental in building and scaling innovative solutions across various industries, driving both product and business growth. His contributions have helped organizations navigate complex challenges, launching products that resonate with users and generate meaningful value. While he’s a self-professed tech geek, Kyle’s true passion lies in helping people solve problems through technology. His approach is grounded in a belief that there’s always a better way to do things, and he thrives on challenging the status quo. Whether leading product development or mentoring teams, Kyle is deeply focused on simplifying workflows and creating solutions that deliver measurable impact. His hands-on leadership style fosters collaboration, empowering teams to push boundaries and achieve successful outcomes. Obsessed with knowledge and driven to share what he learns, Kyle enjoys troubleshooting, problem-solving, and improving processes to create lasting impact. His relentless curiosity and commitment to continuous learning ensure that he is always evolving, finding new ways to drive innovation and inspire those around him. He is dedicated to the idea that technology, when applied thoughtfully, can transform how we work and live.

VanillaSoft Webinar: Why Cold Calls Burn Bridges: And Hot Calls Build Relationships – July 10th @ 12pm Eastern

Posted on May 22, 2025July 1, 2025 by Kyle James

Date: Thursday, July 10th Time: 12:00 PM ET, 9:00 AM PT In today’s sales environment, cold calls aren’t just ineffective—they’re a liability. Buyers are flooded with impersonal outreach, and the “spray and pray” approach is more likely to burn a bridge than build a pipeline. Join sales experts from VanillaSoft and 3Sixty Insights as they unpack how modern, data-driven calling strategies are helping top sales teams connect faster, convert more, and build real relationships. You’ll learn: Why cold calls fail—and how “hot calls” solve for timing, context, and trust The sales data proving the resurgence of the phone in buyer engagement How to identify and act on engagement signals to prioritize the right leads The psychology of timing and how it impacts conversions A practical, […]