Take THE

Wider View

Candid thoughts from inclusive leaders

View all of our newsletters and webinars on The Wider View.

Share on linkedin
Share on twitter
Share on facebook

Ken McDonald

General Manager at Togetherwork

Ken has been involved with growing and managing Internet businesses for the past two decades. He currently is General Manager at Togetherwork, a SaaS and payments company, where he oversees five different product lines.  Previous he was General Manager at TeamSnap, an app to manage sports teams and clubs.  Ken helped build TeamSnap from an early stage company to one with over 21 million customers and 5,000 B2B customers.  Ken is a co-author of How to Acquire Your First Million Customers, a book that draws from Ken’s experiences in growing Internet business to millions of users.  Ken has an MBA from Stanford and a BA in Math and Economics from Dartmouth.

Ken has a wife and two kids and is an avid athlete.  He has completed roughly 100 triathlons all the way up to the Ironman distance.


Finish this sentence: I wouldn’t be where I am today if it weren’t for ________________.

My parents. My parents always had high expectations for me without putting undue pressure on me. They seemed to know those times when I had enough drive to succeed and those times when I needed a push. Often they focused more on ensuring I had the right values (e.g., they were big on honesty) without trying to micromanage every last detail of my life.


Resumes highlight professional and educational achievements. Which one of your life or personal experiences deserves to be on your resume?

Several years back I signed up for a 106 mile mountain bike race. Before the race, the organizer made us promise to ourselves that we would finish the race no matter what. His comment to us was, “You are better than you think you are.  You can do more than you think you can.”

The bike course was incredibly sandy and within the first 4 miles my gears gummed up and my 27-speed bike became a single-speed bike, far from ideal on this hilly course.  What was already a daunting challenge had suddenly become seemingly impossible.

However, I remembered what the race organizer had said to us, hung tough, and finished the race with a solid time.

After the race, I taped the organizer’s comments to the wall to remind myself that we can accomplish much more than we think.  Never settle!


What qualities do you look for when hiring someone on your team? What qualities do you avoid?

In the technology world, you never know what challenges you are going to face in the future. As such, I need people who are tenacious and good at overcoming new problems. I typically ask people during the interview process what challenges they have overcome in life.  I want to ensure they can tackle whatever comes their way on the job.

I try to avoid people who are not coachable. If someone is going to work well on my team, I need to learn from them, and they need to learn from me.


Sharing DEI data, including the good and the bad, and talking about your strategy for improving, is essential.”


Is there a time when you were told to change yourself, or hide some aspect of yourself to be accepted or successful in a situation? How did you react?

In 1943 my family changed our last name to hide our Jewish roots. Because my last name is now “McDonald” people are unaware of this. Sadly, I have heard a number of anti-Semitic comments and jokes over years particularly in business settings. In these settings, the easiest solution would be just to ignore the comments and essentially pass. Instead, I have done my best in these cases to educate the person making the comments. Often their misunderstanding of Jewish history has resulted in negative stereotypes and perceptions.


Which three books, podcasts or news sources do you think everyone should read? Why?

I encourage everyone coming out of college to read “Startup of You” by Reid Hoffman. The book talks about how you need to take ownership of your career and how technology allows you to learn the skills you need to pursue the career you want.  It is a powerful message that helps you throughout your professional journey.

I think everyone should have one foreign news source on their list. It really doesn’t matter so much which one so much as that you have one source that gives you a perspective of how other countries may be perceiving what is happening in the world. Every time I turn on a foreign news source, I am always amazed by how differently current events are portrayed.


Diversity, equity and inclusion is front and center right now. How do you express your commitment to diversity, equity and inclusion in your personal and professional life?

A number of my Stanford business school classmates and I decided that we wanted to see what we could do to drive more change in the area of DEI and created the Racial Equity Playbook. The idea behind the playbook was that many organizations want to become more diverse and inclusive, but don’t know where to start. The playbook is a place where people can get some pragmatic ideas for how to get started in becoming more diverse and inclusive.

I work at Togetherwork and we have been implementing many of the core concepts in the Racial Equity Playbook. For example, we have published our employee census numbers in extensive detail and provided a lot of detail on where we are doing well and where we have work to do. This level of transparency has increased the sense of urgency around the organization. We also have revamped our recruiting processes to cast a wider net and reduce potential bias in the interview process.


What do you find most frustrating about corporate DEI initiatives and what’s one tangible step every employer should take to help build a more representative organization?

As the saying goes, you cannot improve what you do not measure. I find it frustrating when companies say that DEI is important but are unwilling to measure how they are doing or are unwilling to share that data with everyone in the company.  Sharing the data, including the good and the bad, and talking about your strategy for improving, is essential. Making progress on DEI takes a village and you only get there with transparent communication on how you are doing as a company.

Want more of this content in your inbox?

View all of our newsletters and webinars on our Resources page.

Ken McDonald
Skip to content