Ep. 159 – Dialpad COO, Jason Yang


Our guest today is Jason Yang, COO of Dialpad. Jason joined Dialpad in 2018 and was previously SVP of Marketing and Business Operations.  He brings to the role more than two decades of experience with high-growth global companies and a wide breadth of experience across disciplines.

Jason is a global marketing and digital transformation leader with experience in successfully delivering against complex and challenging business objectives. Adept at strategy, technology, and people to drive demand, fuel business growth, and build great brands.

Jason acquired broad industry experience across SaaS, financial services, brand management, healthcare, and consulting. He has strong analytical expertise and a mindset for data-based decision-making. Jason is recognized as a top leader and coach that builds high-performing teams.

Previously, Jason held leadership roles at Five9 and Charles Schwab.

In This Conversation, We Discuss:

  • How the field of telephony adapted during the COVID-19 pandemic and how cloud-based telephony grew and took its place
  • In what areas call centers struggled in the last year
  • How Jason excelled and grew into the role of COO
  • The ups and downs Jason had to go through in the company
  • How to handle cuts and layoffs, and how to communicate to the survivors
  • How to move away from the rift and into the new phase forward



Connect with Jason Yang: LinkedIn

Corcentric – https://www.dialpad.com


Connect with Cameron: Website | LinkedIn

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The post Ep. 159 – Dialpad COO, Jason Yang appeared first on COO Alliance.

Before we jump into this episode, you need to know about two important ways that we can help you and your company grow. Number one, check out the COO Alliance. It is for COOs, Presidents, VP Ops or whoever is your company’s second in command to the CEO. The COO Alliance is the world’s leading community for the second in command and it gives COOs the tools and connections to grow themselves and the company. Head over to COOAlliance.com to learn more about our members, the results, the program and our 10X guarantee. If you qualify for membership, you can set up a complimentary call with our team to discuss if it’s right for you. I will tell you about number two in a bit but first, let’s start this episode.

Our guest is Jason Yang, COO of Dialpad. Jason joined Dialpad in 2018. He was previously SVP of Marketing and Business Operations. He brings to the role more than a few decades of experience with high-growth global companies and a wide breadth of experience across disciplines. He is a global marketing and digital transformation leader with experience in successfully delivering against complex and challenging business objectives, adaptive strategy, technology and people to drive demand, fuel business growth and build great brands.

He acquired broad industry experience across SaaS, financial services, brand management, healthcare and consulting. He has the strong analytical expertise and a mindset for database decision-making. He is recognized as a top leader in coach that builds high-performing teams. He held leadership roles at Five9 and Charles Schwab. Jason, welcome to the show.

Thanks, Cameron. It is great to be here. Thanks for having me.

I’m looking forward to it. I’m curious what it was for you that had you see Dialpad as your next step because you have been there for a few years. What was it originally that grabbed your attention?

I was in the industry. It is the first and foremost thing. I was at Five9. We were in the contact center industry. What grabbed my attention was they had an awesome product that was built for the cloud and a modern workforce. I could see where it had potential. When I met with the CEO there, we had a great breakfast, which is how these things get done. We talked a lot about the future and what it could be. I bought into it and I felt this was a company that had a lot of potentials. More importantly, I thought I could make an impact there with the experience that I had. I was excited to jump at the opportunity.

I’m going to come back to that in a second but I want to go back into your career a little bit and talk about the contact center business. Contact centers or call centers are tough industries to be involved in. There are a lot of people, moving parts, technology and staffing issues. What are some of the big lessons you pulled from that? How big was Five9 when you were working there?

Five9 was roughly $300 million in valuation when I joined and when I left, it was $2.1 billion. It is a complicated industry. There are a ton of upfront stakes. Telephony is hard. It is hard that not a lot of people want to get into it. To do it well, do it reliably and do it with a high level of serviceability, like four-nines, five-nines and six-nines, is a difficult thing to do. It is complicated. There are all these other things you have to get right. You have to turn that telephony that you have built into a servicing process so that other orgs can make better decisions. You got to turn it into a reliable process so people within a company can make their changes and be empowered to move nimbly and operate their businesses.

You got to give them intelligence about data. What questions are coming to the call center? How do you pivot quickly to make a change so you can improve your service response and not have a massive call spike and hundreds of frustrated customers on the line? Standing up in a call center is a tough thing. Sometimes you got to do it quickly and in a way that impacts hundreds, if not thousands of people. There is a whole art to that process and the way you roll it out, the way you install it and displace maybe an income PBX system are complicated issues.

In terms of them being complicated, one of the divisions I ran at 1-800-GOT-JUNK? was our call center at one point. What baffled me was all the telephony sides of it. The people stuff was easy for me but with all the equipment, switches and everything, I still don’t understand it. How did all these businesses that have contact centers or were contact centers make this pivot with COVID to run these things from home? What did they do? Is that going to impact that entire industry going forward?

COVID accelerated the adoption of the cloud-based contact center or cloud-based telephony communication platform by about ten years. It is almost overnight. People could not run their businesses. They had to find alternate ways, sometimes hybrid ways, sometimes hybrid moving to the cloud 100% to provide service and have employees that can work from anywhere who expect to be able to work from any device anywhere with reliability. On top of that, not just providing the technology, which is no longer a hard wire to a phone or a computer at a physical desk, now you have to be able to provide the training.

SIC 159 | Dialpad

Dialpad: COVID really accelerated the adoption of the cloud-based contact center or cloud-based telephony communication platform by about 10 years.


In our company, we have hired a couple of hundred people and none of them have ever met face-to-face. With the vaccine rolling out, all of that is going to change soon. We had a whole year where we had hundreds of new hires and we have never met anybody. We are a great example of a work-from-home DNA culture where we did not miss a beat.

A lot of companies are like us. They hit that accelerator. They realize they could shift to working remotely. People realize it wasn’t bad. There is initially a little bit of fear. Would people be as productive? I would argue most people who work longer hours are more productive to the point where companies are thinking about how do we rebalance the other way. That whole shift has been transforming in this environment of the pandemic.

Dialpad has been able to participate in that. One of the things that we did to our home was, early on, we gave away the product. At the beginning of the pandemic, we said, “If you need it, come use it.” We gave it away to 500 customers, people or businesses, who came and signed up. It was unlimited, all you could use and be helpful to the world. A vast majority of those are still our customers now, as a testament to trying to do the right thing but also doing the right thing sometimes reaps good business results. We are happy to see that they continued with us.

Doing the right thing sometimes reaps good business results.

I’m going to ask about Dialpad and start diving in there in a second. You are right in saying that this change with COVID moved these call centers and contact centers ahead by ten years. I don’t think any of them would have ever thought it was possible or that they ever would have wanted to move remotely like it would because they are stuck in adding the next 100,000 square feet and the next teams of people. It is extraordinary. Where did that industry struggle? Was it the onboarding of people? Was it finding new technology that could work in the cloud? What was it?

I will give you my personal take on it. We were already at the beginning of a transition from a PBX platform to a cloud platform in most cases. A lot of times, you had new leaders coming in who maybe had seen some of the newer technologies and could see the value of it. They always ran into the physical limitations of the on-premise system and had to flex to accommodate some existing legacy connector or something that they had to have to keep part of their business running. There is a lot of inertia to these kinds of change changes.

Typically, when you have infinite time, the rotational cycle for your contact center platform might be about seven years. You might buy a platform and keep it for seven years. The pandemic changed that. Overnight you had to figure out a better way. Most people move to figure out a better way and they have to do that to keep their businesses running. It is a little bit of dipping your toe in the water.

Once you realize that the world is not riskier on the other side, you can see change and be more efficient. Your IT team could remotely manage everything from anywhere. It is pretty transforming and it is green. It creates a lot of conversations that there isn’t that big bad downside. Looking forward, what is the best way to do this? We have a workforce that works from anywhere. We probably hired many others because we have been able to hire from anywhere. There are even some geo-arbitrage things happening. When you factor all that in together, you got to be prepared for a modern workforce. Part of that is giving them all the right tools to do that.

Talk about the tool. What is Dialpad? What do you guys do as a company? The timing for you with COVID has probably been quite strong.

It is a business communications platform. It is all based in the cloud and it does everything from conferencing to contact center. It is one platform that has phone video messaging and we layer real-time artificial intelligence across all of that. That helps you make better decisions, mind your data and take meeting notes. That is what it is. If you are a modern business looking for a modern platform to work from anywhere, this is the thing that helps you do it and it helps you spin it up for any employee you have anywhere in the world.

Who are your customers? What is your customer demo?

We do a ton of business in most of the segments. Historically, a lot of SMBs and mid-market are increasingly upstream into the enterprise. Many customers over $1 million in terms of deal size. We have seen expansion across all segments. That is because the use cases tend to be similar. People are looking for ease, good user experience and intelligence that AI can provide. All of those resonate with every segment, maybe in different ways than some but they have value. When people look at the product and they get a demo, they are like, “This is cool.” We do participate in all of them.

Has there been one niche that maybe has adopted this more because of COVID? Was that unexpected for you?

There hasn’t been one particular sector or area that, by a factor of ten or anything like that, expanded. We saw a good rising tide lift across the entire business as a result of COVID. It came at different times. At the beginning of the pandemic, business slowed down a little bit and some businesses picked up faster than others. Everything is much has been rebounding. We are seeing good traction everywhere. One of the things that we have been able to nail is you may have seen our partnership with T-Mobile. That has been good validation of having a modern solution that works and that is focused on the mid-market enterprise segment.

We are proud of that because it is a third party coming to say that we have a solid product that they want to have as part of their T-mobile collaboration. They have been working with us for some time. They participated in our funding round. We have been able to get good traction with them and a lot of interest from seeing that. We think that mid-market enterprise space is optimal for us.

You raised another $100 million plus.

I think $126 million.

What was the round before that?

It was about $50 million before I got there.

Did anything change in the time from when you got there to this round coming through? Is it business as usual or is this going to accelerate things? What is changing with this big round that is coming in?

When you get more funding, you want to deploy it in smart ways for growth. It did help to give us the fuel. We wanted to grow. Years ago, the company was in the process of figuring out what is the right move. What is the right recipe for success? How do you go to market? What is your pitch? How do you sell? How do you service?

SIC 159 | Dialpad

Dialpad: When you get more funding, you want to deploy it in smart ways for growth.


Once we had figured that out, I almost imagined that being the analogy of like this, you figure out how to make a little tiny fire. Once you know how to make that flame, it is about scaling it and pouring gas on it to grow as fast as possible. That is where we are. We figured out the recipe and it wasn’t super easy. We had some iterations and we can get into some of the ups and downs of that but once we figured it out, it was about like, “How do we resource this? How do we grow? What you are seeing is we have had massive hiring. We are over 800 employees. At the end of 2021, we will be over 1,000.

How many were there when you got there?

I was number 365. It was pretty significant growth.

It wasn’t a small company when you got there. You came into a solid seasoned leadership team and then you are in the COO role. What was it that brought you into that role? How did you excel and get to that role?

I’m a first-time COO. I have been in the role for a few months but I have been in the responsibility set for much longer than that. We made it official. The problems I have been solving haven’t changed from before and after getting the title. Coming into that team, the thing for me was I started as the Demand Gen Leader. I have moved to take on all of the operations. I caught all the toss-ups for a lot of like, “How do we solve these amorphous problems?” Doing so gets you this exposure to the company where you are contributing in every department.

Were you putting your hand up and saying, “Yes, I will take that?” Is that what happened or was it being tossed on your plate?

Some of it was being voluntold but mostly volunteering. I love to solve problems. I wasn’t expecting the role. Even back then, in the infancy of the company, I don’t think we were even sure we would ever even need a COO. That was fine. The title didn’t matter. It was more like, “This is what we need to be successful. Let’s go solve these problems.” Getting the breadth of experience is what set me up to be in this position.

I don’t know if you follow the HBR articles about the different types of COOs. If I had to break myself down, I would say, “I’m part executor and part the other half.” It is about how you compliment your CEO. Our CEO is an amazing guy and brilliant. He is a product focus. I’m good at the details. I come in and I crush the details to run the business.

I wonder if you are similar to Harley Finkelstein. Do you know Harley from Shopify?

I haven’t met him. No.

Harley was demand gen biz dev sales marketing and Tobias Lütke, who was the CEO, was product and engineering-focused. You guys may be similar in that role. You are right that the visibility of demand gen and being there on the revenue side probably got you noticed inside the business. What got you respected was taking all these projects and initiatives and being able to do them and solve the problems. How about with the CEO? What is your relationship with him?

We have a great relationship.

How do you work on that? Is it always easy every day or have there been struggles with that?

Easy is probably not the right word. Work is work. You are all trying to solve problems. You have the best interests at heart but sometimes there are direct, brutally honest conversations. Part of having a good working relationship is to be able to have those conversations. I respect the guy. I love the guy. He is my friend. His name is Craig Walker. I was at his house for dinner. We get along great. When we need to have an upfront conversation, we will and it is direct. That is what I value about it.

Part of having a good working relationship is to be able to have those brutally honest conversations.

Is that why you can have the upfront conversations because you have that underlying trust and respect for each other like Pat Lencioni in The Five Dysfunctions of a Team? He talks about the fear of conflict and the absence of trust. It sounds like you have good healthy respect in both of those areas.

We would not function if we didn’t have that level of trust and respect for each other. You don’t want your comments to be couched and be like, “What is that person thinking? What is the question behind the question?” It is black and white. State how it is and we will agree, disagree, discuss and move on. We both have that mutually. That is why we can shortcut a lot of things. You don’t have to worry about some of the chat.

Is the company changing because of this last raise or is the company changing at all because of some of the big growth from 365 people to pushing to 1,000?

We are still a startup. It still feels like you can throw spaghetti against the wall and see what sticks but if I had a charter, I’ll do that in a much more predictable and scalable way and do it in a way that can still fuel hyper-growth but without any waste.

It is funny you mentioned throwing spaghetti against the wall. I showed my child how to do that. He thought I was crazy but I’m like, “That is how you know it is done. You toss one against the wall. If it sticks, it is ready.”

It is a business. You still need to have the DNA to take a little risk, do some testing and try new things. There is a little red tape. If you look at my resume, I have worked at some pretty big companies. I could tell you there is more red tape there. We pride ourselves on being light and nimble. That is part of our competitive advantage. We try hard to keep that going.

Have things changed other than adding huge numbers of employees and being able to do a lot more? Yes, we are trying to be a little more formal and structured. When you have bigger budgets, you are trying to deal with better reconciliation of where your investment went and what the ROI was. You are trying to be more buttoned up in general.

Were you guys all based in the Bay Area before COVID?

We always had offices globally but the Bay Area was the headquarters. We have a huge office in Austin. We also have offices in Kitchener, Canada. We have a big office in Japan. We have people in Australia and MIA. We are all over and we are continuing to expand.

Is MIA in Middle Eastern and Asia? What is MIA?

When I say MIA, it means Europe.

Kitchener was the hotbed from research in motion from where Blackberry blew up. You are hiring everybody out of the University of Waterloo. Is that why? Was it an acquisition? What happened there?

It wasn’t an acquisition. Kitchener was a search for talent in a place that no one else had yet gone to. I’m sharing this on the show. It won’t be a secret anymore. They are great people with good talent. We have been happy with the ability to hire from there because they can work from anywhere. It worked out for us.

The cost of living there is half what it is in the Bay Area. You can pay people. They can have a great lifestyle and you lock them in. Have you been to Kitchener in the winter?

I have not yet been. That is on the list.

Don’t rush up there in the winter. Go in the summertime. I grew up North of there. How about the ups and downs for you in terms of the company? What are some of the ups and downs that you have had to go through?

I was talking about finding that flame in the beginning. The recipe to find that flame is a little different but you try different stuff. Years ago, we had a reduction in force. That was because we had tried a bunch of different motions. They didn’t work. We got to the point where we wanted to knuckle down on our finances and make sure that we were going to be able to scale the parts of the company that we were doing great. That resulted in a riff.

Those are unfortunate, as you can imagine because they impact people’s lives and families. No one likes doing them. That was probably the low point. I will share a quick story. We came out of that probably faster than you think. Our next quarter was a record quarter, followed by another one from the focus. If there was ever a case study for being focused, that was it.

What were some of the lessons you learned from doing that? How would you have done it differently? What do you think you did well in doing the reduction of force that worked well? There are a lot of people out there that have never had to do it. What would they do?

I don’t know if there is anything I would do differently except maybe a little better planning before that happened to maybe not get to that point but the actual way it happened was super respectful, humane and recognizing. These are colleagues. They are not numbers. It was one coordinated effort across the company. It was a short-term, high-action motion followed by immediate group discussion like, “We are a family.”

Walk us through that. Let’s say that somebody is going to have to do a 50-person or 150-person layoff. What do they do? How do they talk about it? How do you socialize it? How do you deal with survivors? Give us some of that. That is rarely talked about. I had to do it a couple of times but I love to hear how you did it.

The first thing is you got to decide how you are going to do it or where it is going to be. For us, we knew we had a business area that probably was not going to make the cut. There is a fleet of battleships. If you have your battleship, you have all the supporting frigates and stuff around it. You are like, “That is not making the cut. What do we need to support that? What supported it?” You go out from there. That is how you arrive at where it should be. You always have to make trade-offs on teams. Sometimes when you have a team of 10 and they go to 5, 2 or 8, whatever the number is, you have to make choices about whom to retain and whom to stay.

Those are objective decisions based on performance and past contributions. In my mind, the one thing I could say is if you were a strong employee that had always gone the extra mile and the more all-around athlete would also be a good one. It could be a role-player. If that is you, you probably don’t have to worry because those people are always valued. At the end of the day, you end up with a list.

SIC 159 | Dialpad

Dialpad: If you were a strong employee who had always gone the extra mile, you probably wouldn’t have to worry because those people are always valued.


How many people were there?

At that time, we have 50.

Did you do it all at once? Did you bring them all down to the lunchroom and hand them all Kool-Aid? Do you give them a letter or one at a time? What did you do?

It was all at once but it wasn’t one big meeting. It was one active morning, where for a couple of hours, it was one meeting after another. If there is no way to do it comfortably but when you do it, that is maybe the most humane. Doing it in a lunchroom is probably the worst and the least humane way of ever communicating that message.

We had 900 employees back in 2000. As the NASDAQ was starting to crash, we had to fire 150 people at once and send them all down from 4 buildings down to our head office in Seattle. I remember one of the girls at our office was like, “Why do I not get to go to the meeting?” I’m like, “Shut up. Sit down.” She was like, “I want to go.” I’m like, “You do not want to go to this meeting. Trust me.” What about the survivors? What do you tell the people that were not laid off? How do you communicate that stuff?

First, you tell them, “Thank you for having been part of the company and you are still part of the company. The reason you are still here is that we believe you are going to help the company grow and we appreciate everything you have done.” There are two things. There is no other issue with the drop. That weighs on people’s minds.

They are waiting for the aftershock.

One of the things we did well is we made sure there was no aftershock. We were clear that now sucked. That is the end of it. Tomorrow we are all going to get up and do better together. That helps. For anyone who’s going through this situation, be clear and honest with people. You don’t have to beat around the bush. People understand.

If we think about the people that are left and the people that you have gone through the communication and the discussion with them and then you are going to rebuild that team, do you realign them with new goals and vision? How can you quickly move away from that rift and move into the future again? What do you do there? You thank them and let them know there is nothing else. Do you flip the gears and drive forward? What happened?

If you are going to make a change like that, you have to have clear marching orders coming out of that if only to keep the company focused. Honestly, anytime something like that happens, there is a little bit of like, “Figure out where the balls are dropping because you can’t account for everything.” Some of it is picking up pieces. In our case, we were refocusing on parts of the business. It was clear. It wasn’t picking up pieces. It was more like, “We are going to focus on this. Let’s all focus on that.” I don’t know if you are imagining there are a lot of gotchas or unexpected. There wasn’t. It was to refocus and it gave us the capacity to do so.

What is your day-to-day that you are involved in? What is your leadership team makeup look like?

I’m involved in most things, a lot of things from a consultative perspective and some things from a direct decision-maker perspective. My team is all of the revenue operations, which in our world, you might call sales and marketing operations combined at other places. It is our data analytics team that does all of the preparation for our financial reporting, even our product feature reporting and utilization things. Our international offices report to me. We expanded the scope to include the customer support organization.

You got a lot on your plate.

I do but it doesn’t feel that way. You probably hear this a lot but if you feel like your job is work, you are going to have enough fun.

How do you prevent yourself from getting pulled into the minutia or areas that maybe you are competent at or could do but you don’t have time for or shouldn’t be doing? How do you prevent yourself from doing the 100-hour weeks, which is a skill that a lot of them, maybe earlier stage COOs, haven’t quite figured out yet?

There are a couple of things. One is you need to have a good bench. You need a leadership team that you can rely on and trust and push decision-making downwards. That is going to help everyone. The second thing is that this is something I like to do. I ask questions. Rather than be the decider all the time, people can get in the habit of coming to, “What do you think about this? Can I have your permission to do that?” It was like, “What do you think? Why do you believe that?” As a trick, I often do that, especially, with people I haven’t worked with in the past.

You need to have a good bench that you can rely on and trust so you can push decision-making downwards.

I will see their thinking and decision-making process. Assuming we are on the same page, often I will say, “For these kinds of things, you decide. Let me know if there are any exceptions.” I might ask something like, “You are not going to get it right 100% of the time but if you get it right, 99 out of 100, that is good enough and we will talk about the one.” That is better than you asking for approval 100 times in a row.

How did you learn or develop that skill? If a lot of leaders don’t develop that skill, they never scale. I don’t even know if you are valuing how important that one is or maybe you are.

It was always a little intuitive to do that. Maybe not a training thing and I don’t know if this has influenced that but over the course of my life, I have subscribed to some leadership training that I liked a lot. One of them is situational leadership. That is probably my favorite one. I have even taken it three times at different points in my career, like refreshers. I ask that every one of my leaders take it so we can speak a common language. That helps. Some of the questions that I asked came from some of them.

The other part is pure survival. At some point, you looked up and you were like, “I can’t be the responder to everything. I can’t answer everything. How do I do this differently?” Try it once as an experiment and it works. You can keep cascading it forward and eventually, it becomes part of your management style. That is how it has become but it always felt more natural that way.

Situational leadership is the core executive functioning skill. I launched a course called Invest in Your Leaders, which is all about growing the leadership team and management team skills. The first of the twelve modules is situational leadership. I did an entrepreneurial version of it, and you have done days of training on this stuff, where I tried to simplify it in a way you can use it in a much more entrepreneurial, faster fashion than the traditional model of situational leadership.

Dr. Paul Hersey and Ken Blanchard crushed it with that whole model. The One Minute Manager, even though it was old is still probably one of the best management books of all time. Were you raised by parents who had you figured out for yourself versus giving you the answer or doing everything for you? You were Like, “Mom, can you do this?” Did your mom do it or did she get you to do it?

I would say half and half. They didn’t go out of their way to encourage me to learn from myself. What they did do was teach me to survive. They were like, “This is the world. You need to know how to do stuff.” I will give you an example. If I was trying to like fix something on a bicycle, my dad, who is an engineer, would probably teach me how to do it. He is not going to be like, “Go figure out how to install the pedal.” He would view that as a waste of time, like him not showing me but I learned from that insular childhood.

From the time I entered the workforce, I learned that I probably had some gaps and I wish that I maybe had a little bit more of the whole “go figure out yourself” early on in my life. I was self-aware. I made it a conscious choice to always figure stuff out for myself. That was also to track things too. I’m a big spreadsheet guy. I track everything in my life and I have goals.

If you have a goal, you can figure out stuff for yourself and you have the power of Google, which has been awesome, you can learn anything. I don’t believe there is anything I can’t figure out or at least know enough about to have a reasonable conversation to determine I’m not competent at something and I need a better source of help. That is part of my DNA. I will often probably go the extra amount to do a little research because I do want to know personally. More than your average bear, I’m less reliant on taking the face value of any fact given to me.

You have mentioned the use of data several times. How do you use data in your day-to-day and how do you get your teams to look at the data?

We use it every day to run the business. One thing I learned early on is no one wants to sit there and crunch the same numbers every day. One of the boons for running a business in this modern world is if you have access to something like Domo or Tableau in a data team that can do Python scripting and runs it out of something like a big query. You are using it to do real-time data reporting and not as a mask for whatever was in your Excel spreadsheet. When you have real-time results like that, it saves you hours every day. Those hours add up over the course of a year to productive time that you would have spent going through rope processes and not being able to share that analysis with other people and not having a source of truth.

SIC 159 | Dialpad

Dialpad: From a scalability perspective, no one wants to sit there and crunch the same numbers every day.


One of the best things that we did at Dialpad was creating a source of truth. We were like, “These are the sales results. This is the ARR. This is the churn.” There is no other subjective reporting. There is no additional filter your team wants to put on it because you know some special weird circumstance. You were like, “These are the numbers.” Getting everyone to buy into those into the foundation of it, that it was all coming from objective data and having them understand how it is built. Once we got past that, it was awesome because we have conversations about, “This is the data and results. What are we going to do about it?” It is not, “Do we believe the results?” It is a vicious cycle of like, “If you don’t believe in these numbers and what do we believe in,” you can’t move forward.

Talk about the T-Mobile deal that you did and what you learned as an organization from working with T-Mobile.

T-Mobile was an awesome experience for us. We are part of their collaborative offering and they are reselling Dialpad. They picked us because they told us we are the most innovative solution out there. They wanted someone modern, tech-forward and mobile-first. We were in sync with them from a style perspective, a cultural perspective and a product perspective. They bring this 5G high-speed internet, which enables anyone to work from anywhere. You can take a hotspot or your office could have one of their new 5G routers and everyone is good to go. We bring the software. That combination is powerful.

At one point, I was coaching the CEO of Sprint, Marcelo Claure and I also coached his second-in-command, Jamie Jones, for several months. I found that Sprint was a big complicated decision making. I don’t know if I could have ever tried to do a business deal with them. I was only coaching them because I was friends with the CEO. It seems like T-Mobile was different. Were they more entrepreneurial? Did they move faster or did they seem like a big bureaucratic place?

T-Mobile is more entrepreneurial and they move quickly. We have been happy with them as a partner. Their launch for T-Mobile collaborate and a bunch of other things was one of the best launches I have ever seen in my life. That includes the several years I spent at the Clorox company where all we did was brand launch. They did an amazing job down to the little logos on their lasers. It has been the stigma of big companies being slow or late. I don’t think that is necessarily true. There are bigger companies. They don’t move as fast as a startup can but they move. They have been good partners.

Final question. If you want to go back to when you were 21 or 22 years old, maybe graduating college, what advice would you give yourself back then?

Here is the number one thing and this goes back to my spreadsheet thing. If you have a goal in life, you will work toward it. If you don’t have a goal, you will waffle through day to day. You won’t know. I say this because I made a spreadsheet a long time ago and this is going to sound probably maybe too detail oriented but this is how I am. I made a spreadsheet and I said, “One day, I want to have a family, I want to have kids, I like to pay for their college, I like to retire at this age.” I used all the Excel skills at the time that I had accumulated and I coded this thing. I was excited about it.

If you have a goal in life, then you’ll actually work toward it. But if you don’t have a goal, then you will just waffle through the day-to-day.

I figured out that I wasn’t going to get to this point by this age if I didn’t make some changes in my life. That was an inflection point. You don’t need to build a spreadsheet. That is not how everyone is wired. You need to know if you can get there on the path that you are on. If you can’t get there, you got to be okay with that, which I don’t think most people are or you got to be willing to say, “I’m going to do something different and make some changes.”

It could be a career change, learning a new skill, going back to school or any number of things like working harder to get the next promotion or whatever it is that you need at that time. If you can get yourself a little forward every day and make incremental progress, that compound effect over 20 to 30 years is huge. I promise you. If you can do that, do a little bit every day and try to get to this goal that you set, you will be happy wherever you end up. You may beat your goal.

The key is incremental progress every day and driving towards that goal. If you don’t know you are going anywhere, it will take you there. Jason Yang, the COO for Dialpad, thanks very much for sharing with us on the episode. I appreciate the time.

Cameron, it was a pleasure. Thanks for having me.


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About Jason Yang

SIC 159 | DialpadGlobal marketing and digital transformation leader with experience successfully delivering against complex and challenging business objectives. Adept at integrating strategy, technology, and people to drive demand, fuel business growth, and build great brands. Broad industry experience across SaaS, Financial Services, Brand Management, Healthcare, and Consulting. Strong analytical expertise and mindset for data-based decision making. Recognized as a top leader and coach that builds high-performing teams.


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