33 Years of Sales Wisdom: Thriving in the Winning Culture of Workday

Workday Life
4 min readApr 2, 2024

I’ve had the pleasure of working for multiple successful businesses in tech — each of which are great companies with exceptional leadership and products. For me, the key difference between those companies and Workday comes down to how we truly value, respect and treat each other. We all come from different backgrounds and have varying experiences, yet somehow we are all called to raise questions, concerns or differences of opinions, without fear of reprisal. I think that allows us to accelerate our products, our customer interactions and ultimately the financial success of the company — for which we all ultimately reap the benefits. I cannot imagine working anywhere else. My only regret is not having been among the first 1000 employees here.

Discovering Workday: A New Beginning

I’m Dean Guest, Principal Managing Partner, working in our beautiful Vancouver, Canada office. My Workmate journey started in March 2020, colliding with the Covid-19 lockdown. Amidst global uncertainty, the opportunity to join Workday presented itself as a beacon of stability and purpose. Learning Workday’s values and culture during the interview process, I recognized an alignment that resonated deeply with me. From the outset, my experience has been nothing short of transformative. The warmth of the company’s culture, the camaraderie with my Workmates, and the meaningful connections with our valued customers have enriched my professional journey beyond measure. Beginning my tenure as a Customer Base Account Executive, I’ve since felt an immense sense of gratitude for the opportunity to contribute to the ongoing success of Workday. This remarkable journey continues to inspire and motivate me daily, driving me to uphold the principles and values that define our award-winning workplace.

Empowering Sales Excellence: Leadership in ERP

Our position as a leader in Enterprise Resource Planning (ERP) profoundly influences our sales strategies, particularly when engaging with new clients. Our leadership position affords us invaluable assets, enabling us to effectively engage with potential clients. Leveraging our repository of remarkable customer success narratives, we showcase real-world examples of how Workday transforms businesses, instilling confidence and trust in prospective partners. Our access to comprehensive benchmarking data allows us to tailor solutions that precisely align with the unique objectives and requirements of each client. This data-driven approach not only enhances our credibility but also underscores our unwavering commitment to delivering measurable outcomes. Furthermore, our extensive network of Global System Integrators serves as a powerful advocacy engine, recommending Workday to our own client based on our proven track record of success. This network amplifies our reach and strengthens our position as a trusted partner in the realm of ERP solutions. In essence, our leadership in ERP not only validates our expertise but also empowers us to forge meaningful connections and drive impactful outcomes for our clients.

Cultivating Happy People and Happy Customers

“Happy People Make Happy Customers’’ is a winning strategy. Our dedication to supporting each other leads to exceptional performance, a philosophy that extends beyond our internal operations to impact our customers as well. After closing a strategic Adaptive Planning deal, I sought feedback from the client regarding their decision to partner with Workday. They told me later that they closely monitored our team during the selection process, intentionally challenging us to assess our capabilities. Despite their attempts to test our focus and challenge our assumptions, our objective remained clear, to demonstrate the strength of our team and our ability to deliver complex solutions with precision. Our goal was not simply to win, but to showcase our expertise and commitment to providing unparalleled solutions for intricate challenges, ultimately ensuring our customers’ satisfaction and success.

Embracing Work-Life Harmony: A Journey of Personal Growth

In my capacity as a partner to Workday’s strategy, I face daily challenges that sharpen my business acumen, relationship-building skills, and product knowledge — a journey I wholeheartedly embrace. My manager empowers me to find balance, allowing me to enjoy nature walks, time with my dog, or strolls along Vancouver’s waterfront. The vibrant social culture at our Vancouver office fosters connections, whether over coffee, on runs, or hikes in the mountains. Even amidst the challenges posed by the pandemic, I took the initiative to establish a motorcycle community on Facebook, organizing backcountry adventures during my extended weekends — all made possible by Workday’s flexible scheduling policies, which prioritize employee well-being and enrichment both inside and outside of the workplace.

A Home for All

I wholeheartedly believe that joining Workday is a decision my entire family should consider, especially my children. As we navigate through this exciting phase with our remarkable new CEO and his leadership team, I’m filled with optimism about our trajectory. Our collective efforts to enhance Customer Experience and drive Customer Success underscore our commitment to excellence. One of the most compelling reasons for considering a career at Workday is the opportunity to collaborate with seasoned sales leaders who prioritize mentorship and personal growth. Beyond managerial support, our sales representatives actively support each other through deal reviews, sharing sales strategies, and offering valuable advice. For me, This isn’t just a workplace — it’s definitely home for me here at Workday.

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Workday Life

A view into #WDAYLife as told through our culture and the stories of our Workmates. Your work days are brighter here☀️.