Faces of HR: Kisha Thompson: Cultivating a Culture of Growth at ConnectWise

Kisha Thompson, the Chief People Officer at ConnectWise, is a seasoned HR professional with a passion for fostering a thriving workplace. With over 15 years of experience, Thompson has a proven track record in driving employee development, talent acquisition, and organizational success.

Before joining ConnectWise, she held key HR leadership roles at ClickDimensions and Health Integrated, where she oversaw a variety of HR functions, including talent acquisition, employee relations, and organizational development. Thompson’s expertise in these areas has been instrumental in shaping ConnectWise’s ongoing talent strategy and creating a culture of continuous improvement.

As CPO, she is committed to empowering employees and making a positive impact on company culture. She believes that by investing in employee development and creating a supportive environment, ConnectWise can achieve its strategic goals and deliver exceptional results.

Thompson’s journey into HR began unexpectedly when she accepted a management training program at a custom blinds and shades retailer. Through this experience, she discovered her passion for leadership, team building, and talent development. Her ability to build strong relationships and identify top talent quickly led her to a career in HR.

Ultimately, Thompson’s dedication to her craft and her commitment to creating a positive workplace culture have made her an asset to ConnectWise. Under her leadership, the company continues to thrive and attract top talent from around the world.

In our latest Faces, meet Kisha Thompson.

Who is/was your biggest influence in the industry?

There are a handful of people who shaped my career, but the main one that comes to mind is my Vice Chairman at my first job out of college. He sat me down and told me that he should fire me. He recognized the fight I had in me and understood the direct approach was the key to igniting my competitive side and pushing me to develop the relationship-building skills needed for a leadership position.  

What’s your best mistake and what did you learn from it?

I learned early on in my career that I was making the mistake of trying to build a team of “like-minded individuals” while ignoring my hidden biases towards logic and analytical viewpoints that most reflected my own. I found that my team was lacking the creativity and intuition that it needed. I learned that I’m only as strong as my team and that I needed to create more diversity in my own department and allow for differing opinions or ways of doing things.

What’s your favorite part about working in the industry?

Our 44K-plus managed service providers (MSPs), deliver IT services, such as network, application, infrastructure, and security to small and medium businesses globally. I am amazed at how many MSPs are smaller businesses and/or startups themselves. All of them work so hard, and so many are vulnerable with us about the specific challenges they face. Through sharing results and learning, these individuals spread a wealth of knowledge to their peers. It’s a thriving community and the energy from their passion is infectious. 

What’s your least favorite part, and how would you change it?

We need more diversity across all levels in this industry.  It’s gotten better, but it’s marginal. I would encourage businesses to keep their talent pool diverse by casting a wider net. We can’t always stick to what we know. There are so many universities and organizations that offer access to a diverse talent pool. These resources are excited to partner with companies and create opportunities for candidates who may not have had the visibility to these roles without their help.

ConnectWise is focused on expanding our talent pool. For example, we partner with local universities but are branching out to HBCUs and Women’s Colleges. We have also had success partnering with Hiring Our Heroes and helping veterans return to the workforce. There’s no use pretending this topic isn’t an issue, and I support talking about it openly and transparently. For candidates, I give the same advice. Apply for those roles you’re hesitant about. Additionally, internal candidates should keep putting their names in for promotions (without assuming they won’t get it).

It sounds like through your experience you really care about people, and you want to help them feel safe and comfortable, which is important in the industry. Please elaborate here.

Not enough companies focus on ensuring their employees truly feel safe and comfortable. This doesn’t just apply to their physical safety. Providing a safe and comfortable environment is critical for promoting the physical and mental well-being of employees. When employees feel safe and comfortable, they are more likely to be engaged, productive, and satisfied in their roles. This foundational sense of safety reduces stress levels, minimizes the risk of accidents or injuries, and supports overall employee health, which in turn fosters a positive company culture.

When employees feel safe expressing their ideas, concerns, and feedback, it creates a supportive and inclusive culture built on trust, collaboration, and open communication among employees that enhances teamwork and innovation.

How can HR most effectively demonstrate its value to the leadership team?

HR should provide proactive solutions and data-driven insights, align goals with organizational objectives, and guide the company’s culture. HR should also serve as strong advisors to the rest of the executive leadership team regarding talent management strategy and leadership development and coaching.

Where do you see the industry heading in five years? Or are you seeing any current trends?

With the rapidly evolving technology landscape, there’s no doubt generative AI tools will play a role in the future of the HR industry. Nearly all Fortune 500 companies used some form of automation in their hiring processes over the last few years. Fast forward to today, and the benefits are clear. AI tools can be used for employee training, hiring and recruiting, and more, reducing the amount of time for employee training and candidate screening and streamlining processes for HR and recruiting professionals across departments.

In the next five years, I anticipate that AI tools will be even more engrained in the HR field, particularly as we start to see more companies enact AI plans, strategies, or even designated AI-focused roles. What an exciting time for the IT industry!

What are you most proud of?

I don’t think I have one specific element I’m most proud of, but I’m proud of my career, the teams I’ve worked with, and hearing my sons say they look up to me. What truly makes me proud is the growth mindset I have cultivated along the way. I have embraced challenges as opportunities for learning, and I have never been afraid to step out of my comfort zone despite feeling hesitant at times. This mindset has allowed me to adapt to changing circumstances, embrace innovation, and continuously improve. 

As I reflect on my career journey, I am grateful for the people, experiences, lessons, and achievements that have shaped me into the professional I am today. So many people played a critical role in helping shape my career, and I am excited for the future possibilities that lie ahead. 

Do you have any advice for people entering the profession?

My advice would be to never stop learning. Always ask questions, seek alternate perspectives, and leverage the thought leaders in your own organization. This is an ever-changing industry and natural curiosity goes a long way!

Anything else you’d like to add? We can talk about anything you’d like to discuss here.

True innovation is unlocked when diverse opinions are exchanged to solve problems. When inclusion is inspiring and not a “check the box” exercise, it ignites innovation across entire teams. 

While I feel we are moving in the right direction, there is still work to be done to encourage inclusion in the workplace. Advisory councils, in all industries, exist for a reason–we intrinsically understand the need to gather differing expertise and perspectives to solve problems. However, this same approach needs to apply within our own organizations as well. Only then can we truly begin to learn from each other’s contributions.

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