Dave Wilkins

Member Since 2022

Dave Wilkins


Lakeside Software

Boston Area

David Wilkins is a proven senior executive with 20+ years of talent management experience across a variety of roles, including strategy, product development, marketing, and sales. David has an unbroken track record of recognized success, awards, promotions, and measurable achievements at multiple companies in multiple roles. David was a transformational leader at HealthcareSource driving both marketing and company strategy. Prior to joining HealthcareSource, he was one of two founding members of the Oracle Sales Academy, Oracle's global sales enablement function which now serves over 25,000 sales professionals across all sales roles. David is a recognized industry thought leader and expert with over twenty publications and multiple keynotes at national industry events including ATD, ASHHRA, and Training shows. Leadership Specialties: * Strategy and subsequent execution of strategy through concrete, achievable milestones * Leadership, especially building dynamic, engaging, authentic, high-performing teams * Results through innovation, execution, and a relentless focus on continuous improvement * Flexibility, adaptability, and creativity to hit results even in resource-constrained environments Domain Expertise: * Marketing, especially Challenger Customer strategies and practices * Consultative selling, product marketing, product management, thought leadership, Challenger selling * Talent Management strategy, tactics, and innovation * B2B business strategies and execution including bundling and solution selling * SaaS business strategies and execution including “bridge” sales tactics and “journey” selling * Public speaking: 50+ national and regional conference sessions, including workshops and keynotes * Market Research and Content Marketing: multiple research projects, white papers, numerous industry by-lines, blog posts * Presentation skills across multiple mediums including Power Point, podcasts, webinars, discussion technologies


  • Strategy
  • Product Marketing
  • Product Management


Lakeside Software

Lakeside Software is a leader in cloud-based digital experience management. Lakeside's Digital Experience Cloud gathers and analyzes data on everything that may impact end-user experience and business productivity, and provides the unmatched visibility IT teams need to design and support rapidly changing digital workplaces. Customers use Lakeside's technology to perform end-user experience management, digital workplace planning, IT asset optimization, remote work management, and proactive service desk operations.


  • Big Data for End User Computing
  • VDI Assessment
  • Modeling