A little about who we help and who we are…

Who We Help

Sales management teams often face challenges when it comes to training and coaching their sales teams in empathy-driven selling skills and strategies. At WIN WIN, we specialize in helping sales management teams effectively train and coach their teams by placing empathy at the core of foundational, advanced, and modern best practice selling skills, strategies, and techniques. Our comprehensive training and coaching solutions enable sales leaders to devote more time to assisting their sales representatives in maintaining a customer-centric approach and advancing opportunities, ultimately leading to increased success in closing deals.

How we Serve:

The People:

  • VPs and Directors of larger teams

  • Sales Managers of smaller teams

  • Sales Driven CEOs running sales departments

The Problems We Solve:

  • No formal sales process

  • Untrained salespeople

  • Team Members with personality blind spots impacting their success

The Promise to our Customers:

  • Increased revenue

  • Stronger and more productive teams

  • Highly trained sales team who execute best practice foundational, advanced, and modern selling skills with customers

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Who We Are

Introducing WIN WIN - Empathy Driven Sales Training, a transformative company founded by Kyla O’Connell, a seasoned professional with over two decades of experience in training, coaching, and developing high-performance sales professionals and leaders.

Right from the start, Kyla showcased her prowess by achieving impressive sales accomplishments across diverse sectors, including IT, golf course management, and upscale hospitality. Notably, she sold out a private club membership within a mere six months and spearheaded a remarkable 200% revenue increase for a consulting firm product line in its inaugural year. Her exceptional ability to deliver results became evident when she successfully boosted membership in an upscale private society club by an outstanding 40% during her first six months of management. This achievement did not go unnoticed, and prominent figures urged her to establish a marketing and sales consulting company.

In response, Kyla launched DRIVEN Sales & Marketing in 2003, a boutique consulting firm specializing in assisting small companies with marketing strategy and execution.

Over the years, Kyla's expertise and reputation grew, leading to a partnership with a Washington D.C.-based sales training firm where she continued to excel — training and coaching thousands of high-performance sales professionals and leaders both domestically and internationally. Her reach extended to multinational clients in countries like Belgium, Germany, Portugal, Canada, and China.

Recent years saw Kyla working closely with one of her largest clients, serving on a sales management team responsible for managing over $120M in revenue. Under her guidance, several of her direct reports experienced phenomenal growth, solidifying their positions as top sales professionals within the company.

Driven by a passion for helping others achieve their highest potential, Kyla recognizes that empathy is the key to effective influence, whether dealing with customers, team members, direct reports, or even children. By understanding what truly matters to others and assisting them in reaching their goals, she has honed her ability to lead teams to show genuine empathy towards their customers.

Now, with the establishment of WIN WIN - Empathy Driven Sales Training, Kyla's vast experience in the sales training industry and her innate leadership skills converge to create a company committed to mutual success for both salespeople and customers. Through empathy-driven approaches, WIN WIN seeks to elevate businesses and individuals alike, fostering genuine connections and ensuring triumph for all involved.