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People Processes Interviews: James Sinclair
Episode 3415th May 2020 • People Processes • Rhamy Alejeal
00:00:00 00:59:49

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James Sinclair is the CEO and co-founder of the EnterpriseAlumni as the market-leading alumni in the retiree engagement platform. 

EnterpriseAlumni is a multinational software corporation that develops enterprise software that manages corporate alumni and retirees of large companies like Google, P&G, Pearson, etc. 

James has a background in large enterprise innovation and has worked for companies like IBM, SAP, and EDS. He also contributes to media on the future work of large enterprise innovation and entrepreneurship. 

What Do You Think About the World of People Working for The Same Company Being Over? 

The reality of this situation is that people are more mobile, they are more willing to move. They don’t feel the need to stay with a company for life as our fathers or grandfathers did. As there are more opportunities in the market, there is more desire and value in moving elsewhere and getting a diversity of experience. People are going to move jobs, often. There is a saying “My grandfather had one job his whole life, my father had three, and I have three right now.”

How Did You End Up in This Field? 

I have always worked in the large enterprise innovation space with large customers that are moving from on-premise to the cloud. During this, they have to bring the process that they have spent millions of dollars in creating. We taught companies that ANY idea you have, you can bring to market using software inside 90 days. There was no problem as complex that software wasn’t able to adapt to the cloud. So after a lot of investigation and research, we realized that there was a massive gap in available tools, mainly around a challenge in finding the right candidate due to talent shortages and high cost. My solution was that our former employees are the greatest talent pool we can possibly get. So I created my platform, EnterpriseAlumni  

What Was the Biggest Challenge You Faced In Your 7 Year Journey In Running EnterpriseAlumni?

Today, we are in the middle of a pandemic, and it has forced us to think about our business growth, our customers, and employee status. This has been the biggest test of our company’s resilience and the culture that we have created. At EnterpriseAlumni, our team is like a family. We openly discussed the possible implications of our customers from different sectors, and we know many are suffering. We devised a plan to personally go and take care of all the burdens that they are facing while they work to keep their business running. It was a challenge for us because we had to change our entire business model for them, and they appreciated our gesture. 

Why Are Your Ex-Employees Important and What One Should Be Thinking About in Terms of Business Resources? 

It doesn’t matter if you are a small business or a Fortune 10 company, you spend a lot of time and money on recruiting people, training them, and teaching them how your business works. Then, when they leave, they take all this knowledge and contact with them. This is not the way to off-board someone you have invested a lot of money in. Instead, you can maintain a relationship with them in which you are able to benefit long term. This helps in increasing productivity and boosts the morale of the workforce that is left and gives you the opportunity to re-hire them after they gain more skills and contacts. This will help your business be more successful. 

Why Should a Business Have a Smooth Leaving Process? 

Leaving is inevitable/ In the years that I have worked, I have observed that many employees leave on a bad note because the employers are reluctant to let them go. No matter why they leave, the employer and remaining team feel “betrayed.” These employers fail to see the opportunity and the benefit they could get if they retain a good relationship. If the exit is done smoothly, there is a high chance that they might come back after gaining more skills, but only if you remain in contact. 


James Sinclair has come a long way in his 7-year journey while running EnterpriseAlumni. He advises the companies on how to maintain a good relationship with their ex-employees and stay in touch with them by establishing an excellent alumni network within the organization. One should recognize the culture and sow the seeds from before these people are hired and make their leaving process as smooth as possible. Check up on them or meet up for drinks and wish them well for the future.

Learn more about James Sinclair here: