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Brett Caldon

Brett Caldon: A Compassionate Leader Nurturing Human-Centered Environment

With more than twenty-five years of experience in financial services and leading organizations, Brett Caldon follows these wise words of Steve Jobs. Currently, Brett is the CEO and Co-founder of Workgrid Software. Let’s reflect on the inspiring story of this passionate entrepreneur.
Brett started his career in a large Fortune 100 firm. During mid-90s, the time of tough job market conditions, it was hard to get a job in the recession. But he got an opportunity to enter the financial industry during that time. Brett always wanted to be in the field of technology, but according to him, he was fortunate enough to get diverse opportunities that compounded over time and has allowed him to succeed in bridging the technology and business landscapes.
He asserts, “Taking risks and embracing opportunities even with uncertain outcomes has been a major factor in my development.” He continues, “Keep a mindset to grow and don’t be afraid to challenge yourself and accept the results, for better or worse, and be authentic in your intent, carry that forward and build on it.
About the Company
Backed by Liberty Mutual Insurance, a leading Fortune 100 global insurer, Workgrid Software is not a typical technology startup. The company focuses on building intelligent workplace software solutions that are purpose-built for an enterprise, by an enterprise.
The Workgrid Assistant, Workgrid’s premiere product, provides a unique platform that integrates with all the common systems and tools found in the workplace from HR, expense management, business applications, office productivity, benefit applications, calendars, and even custom applications to aggregate employee tasks, approvals, and needto- know information into a single, modern consumer-like experience. At the core of the Workgrid Assistant is the Workgrid Chatbot, which provides personalized information and suggestions to employees based on their role, location, user preferences, and conversational history.
Brett’s Views on Leadership
According to Brett, leaders are those who understand diversity in approaches, skill sets and behaviors – whether it’s strategy, execution, mentoring, and building influence, championing their people, etc. Brett is a strong supporter of servant leadership and has the ability to listen, empower, have empathy, and remove obstacles. He believes in providing a continuous learning environment, where team members can learn and grow from new challenges and where innovative ideas can flourish.
Overcoming Obstacles
Like many leaders, Brett has faced his fair share of hurdles, but he’s managed to turn many of his challenges into successes. One challenge he faced early on with Workgrid was the positioning of the brand. It was difficult to define, while maintaining the balance between the backing of a Fortune 100 company in a nonadjacent industry, and educating customers on the value proposition Workgrid provides.
Brett and his team had developed various strategies to overcome this. They put in a significant amount of time and effort collaborating with companies across multiple industries and discussing the value proposition of solving for the pain points that exist in the enterprise digital landscape. It was more about building trust with potential customers beyond the solution offering.
Brett can attest to when you start a new venture with innovative products and services, you hit new hurdles every day, but these challenges help you learn and enable you to move forward successfully.
Awards and Achievements
Brett asserts, “I feel my biggest achievement is the culmination of all the failures, successes, learning, and experiences throughout my entire career. That has allowed me to be in the position I am today.” While getting Workgrid off the ground, Brett and his team have been recognized by several prestigious industry awards such as,

  • Agenda18 Digital Edge Award by IDG
  • 2018 Digital Workplace Award by Digital Workplace Group
  • 2018 Intranet and Digital Workplace Award by Step Two Designs
  • Gartner’s Eye on Innovation Award 2018

Preparing for the Future
Brett’s future plans include a focus on the growth and evolution of Workgrid Software. He is planning to expand the product portfolio to continue bringing new solutions to other enterprises. Moreover, he wants to build the brand to where Workgrid is among the most trusted and valued technology partners in the B2B space.
Brett’s Piece of Advice to Young Entrepreneurs
According to Brett, the idea is just one percent of the entrepreneurial journey. He advises, “You need to understand the whole picture and own it entirely. You don’t have to journey on your own, but you need to be willing to invest in learning and doing things to succeed that will stretch your boundaries. Embrace it.
He further says, “Be open to opportunities that arise. Continuously learn. Pay attention to what’s happening around you and don’t be afraid of pivoting, even if you have to give up on something you’ve invested in. Don’t hold on to a mistake just because you spent so much time and effort making it. Learn from it and apply that learning to what’s next.