Monday Guest Gary Rubinstein

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Get to know Gary Rubinstein

By: Mohammed Alqaq   |  August 14, 2023

I am a passionate leader and trainer with 17+ years of Software As A Service (SaaS) experience in B2B and B2C environments across pre and post-sales; consulting; account management and Customer Success.

On multiple occasions, I have embedded the customer success function within a company leading to improvements in customer retention, a higher share of customer wallet, and improvements in overall customer satisfaction and advocacy.

Today I lead WalkMe’s Customer Success function across the Asia Pacific region – which includes Australia, New Zealand, Singapore, and other ASEAN countries, as well as a dotted line to the Japan team.


We asked Gary to take us through a journey telling us about his career path, how he spends his workday, what advice he can share with someone starting as a customer success manager, and many other questions.

Enjoy reading this interview  

Tell us about your career path?

My first job was in the quick service/hospitality industry.  It is there that I learned about working with customers, hustle, the value of process, and the power of collaboration. 

I managed to land in the tech space by applying for a role with a hospitality back-office software provider – leaning on my industry knowledge to implement and teach the software package to new customers.  And as they say in the classics, the rest is history.

How did you join Customer Success?

Honestly, I fell into it.  I had been in a traditional “Account Manager” role working with perpetual, on-premise software.  The consulting business that I was working with at the time started working with a SaaS solution and I started to manage those customers as well. 

At the time I didn’t even realize what I was doing was called “Customer Success”.  But that became clear when I took on my next role as “Customer Success Manager”.

How would you describe the ideal CSM candidate?

I look for candidates who are passionate about customer outcomes.  To be successful in the role, I believe CSMs need to have strong business acumen, be able to adjust and pivot, respond to change and escalations as well as have a willingness to align business outcomes with the software platform they are representing.

I can’t put my finger on the exact skill or aptitude that encompasses all of these ideas, but I know it when I see it and hear it.  Lucky for me, I have developed a series of questions that helps me find what I am looking for. 😊

What one piece of advice would you give to someone just starting out as a Customer Success Manager?

I know the question asked for one piece of advice, but these four things came to my mind immediately🙂:

 – Listen – customers, internal

 – Learn – product / platform, CS trends, macro-economic impacts

 – Be patient – success within an account takes time, career growth takes time (to do it right); so don’t rush either

 – Be excited – CS is a great career and provides opportunities that aren’t obvious on Day 1

The wider you read/listen, the greater your future opportunities will be.

Can you take us on a journey describing what your workday looks like?

It is easier to describe my week, rather than my day because as a line manager, there are a number of things that need to be done every week.  This includes 1:1’s with all of my direct reports, team meetings, cross-functional meetings, forecast calls as well as a number of customer calls (typically aligned to a major milestone or EBR event).

But every day I make sure I answer any outstanding questions that come from my team.  Because I believe, I can’t finish my day if my team can’t finish theirs.

What makes you feel inspired or motivated?

Seeing those around me succeed. 

What’s one thing that people are generally surprised to find out about you?

I started my work career at McDonald’s.  And ended up giving the “golden arches” the first 10 years of my working career (while at school and College/University) – progressing all the way to Store Manager by the age of 23.

Who do you look up to the most?

Anyone who manages a global team.  Being based in Melbourne, Australia, I know how hard it is to connect with people in other corners of the globe. 

Good global managers seem to take this in their stride – they don’t just assume everyone is in their time zone and make the necessary allowances to ensure everyone is able to participate and contribute.

What are your top 3 priorities now?

I feel that given the macro economic environment, my top 3 priorities are going to be similar to a lot of other CS leaders:

1) Customer retention

2) Using data, helping customers articulate the value story from our solution (therefore driving retention)

3) Working at scale

What advice would you give to Customer Success Managers to grow and develop their careers?

“Always be Learning”.  And not just about Customer Success.  You need to be able to draw on a wide range of resources, soft skills, and general knowledge to be successful in this space.  The wider you read/listen, the greater your future opportunities will be… 🙂 

What’s your favorite book, and why?

It is hard to pick just one book, so I am going to list a few.  Each of these books has had an impact on my approach to Customer Success, which is why they are my favorites.

 – “The Effortless Experience” by Matthew Dixon, et al

 – “Write to Sell” by Andy Maslen – pairs very well with The Effortless Experience

 – “Never Split the Difference” by Chris Voss

I’ve also recently read “Think Again” by Adam Grant.  I can’t see it yet, but I know what I’ve learned in this book is going to change the way I look at and address things moving forward.

» Check out the 10 Books a CSM should read to advance and improve their skills.

Have you had your “I’ve made it” moment yet?

The first thing that comes to mind when I think about this question is that I will have my “I’ve made it” moment, when I see my kids achieve their dreams.  That is when I know that everything I’ve worked for has “paid off”. 🙂

What should I have asked you but didn’t? 

What is it like to live in Melbourne, Australia?  Personally, I think it is the best city in the world.  Melbourne has a melting pot of cultures, food from all over the world, the “sporting capital” of the world, a strong arts and theater culture as well as a busy and safe business district.  It is a location everyone should put on their bucket list.

Where can people go to find out more about you?

The best place is LinkedIn , feel free to reach out and connect with me there.  

 Let me know if you are ever in Melbourne, Australia – we have some of the best coffee in the world and I would welcome the opportunity to share a cup and connect in real life.

Thank you, Gary, for sharing your knowledge and for the opportunity to know you more.

Do you have a Customer Success Leader, Expert, or Influencer you would like to know more about?