Ep. 10 – Staying in Sync with Your CEO and the Company’s Vision with Gadi Shamia

In a company or organization, the second-in-command is the yin to the CEO’s yang. They go across varying business areas and oversee the growth of the company. Gadi Shamia is an excellent example of this. As the COO of the fastest growing SaaS contact center startup, Talkdesk, Gadi is responsible for product post-sales renewals, customer service, professional sales training, and more. He shares how he manages it all and at the same time, supporting the CEO on other areas. Gadi takes us to how he got started in the company, sharing his experiences as well as some tips on how to find the company and CEO you can work with. Discussing also the hiring process, he gives great insights on getting the right people and growing strong leaders.


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Staying In Sync With Your CEO And The Company’s Vision with Gadi Shamia

Gadi Shamia is the Chief Operating Officer of Talkdesk. Talkdesk is the fastest growing SaaS contact center startup with thousands of customers like Shopify, IBM, Peet’s Coffee, Dropbox, Peloton, Stitch Fix and 2U. Talkdesk is funded by Draper Fisher Jurvetson, Salesforce Ventures and Storm Ventures. It’s twice named in the Forbes Cloud 100 List. It was listed as Forbes’ next billion-dollar company or a Unicorn and is also the youngest company ever to make the Gartner CCaas Magic Quadrant. Pretty cool stuff is going to be coming up at Talkdesk. Gadi is responsible for product, post-sales, renewals, customer service, professional sales, training, customer support, business development, channels, talent, legal, people and also supporting the CEO on all other areas. He’s got twenty years of experience in software, thirteen years in SaaS. He founded three companies. He’s also been the CEO at prior companies as well. The largest company that he founded ended up doing $1 billion a year in global business. We’re going to be talking a lot around hiring, communication and leadership. I enjoyed this interview with Gadi and I’m looking forward to being able to share it with you as well.

Gadi Shamia, the Chief Operating Officer at Talkdesk. I’m looking forward to learning a little bit about you. I was introduced to your company by Harley Finkelstein who is the second-in-command at Shopify. I met Harley many years ago. I was in for a tour of their startup and he and I have stayed in touch over the years. In fact, he was probably one of the good inspirations for me in starting the Second In Command Podcast. I’m looking forward to learning a little bit from you.

It’s great to be here.

Where are you coming in from now? What city are you in?

I’m in San Francisco, downtown overlooking Mission Street, right by the Salesforce Tower that is being erected here.

That’s the epicenter of technology. That place is amazing what they’re building right now. Gadi, why don’t you tell us how you got started with Talkdesk where you came into it and what kind of experience has set you up for this?

Once you become old enough it’s hard to walk anyone through your resume because it’s long and boring. I did start my career in technology somehow as an accident. I was studying accounting and economics at Tel Aviv University and a friend of a friend introduced me to an entrepreneur. The startup company was not called a startup back then and they were looking for someone smart. Apparently, I fit the bill somehow and I joined this company. It was almost a garage. We worked out of the warehouse at the closing store of the other founder’s wife. We built ERP software for SMB customers in the Israeli market. It was an exciting opportunity for me. I never worked with technology. I was not a software engineer, but the new creations every day, the new challenge, the new tasks that we had to overcome helped me shape the way I think about working and leading, but also being part of a startup. This was the first part of my journey.

Had you focused on software engineering in school as part of your education or did you just dive right into software business?

When I went to school which was in the early “90s, it was not cool to study software engineering. If you look at which were the hardest faculties to get into back then, it was accounting, economics, business administration and law. It was trivial to get it into computer science in the best universities in Israel. I didn’t even think about it as a career opportunity for myself. I thought of myself as a business person. I want to study something that will help me in business. I want to be practical. I studied accounting and economics as a practical subject. I didn’t practice as an accountant, but this background helped me build an ERP product which is now used by tens of thousands of businesses around the world.

You dove into one of the subjects that I was scared to death of in college which was accounting and finance. One of the things I noticed about COOs or seconds-in-command is they often run varying business areas. We’re the Yin and Yang to the CEO. With Talkdesk, what falls underneath you and what falls under in terms of the org chart under the CEO?

This is an interesting point because I met, during the last few years, many COOs and each one of them have somehow a different mix. I think as you described it correctly, it’s a Yin and Yang. It’s not classically COO run the back office and CEO run the front. In many companies, it’s based on what the CEO and the COO wants to do and are good at. I talked to some interesting mix. I’m running a product. I love it because of my product background. I’m running the channel initiative. I love it because of my channel background. I run everything post-sales which is our customer success team, professional services, support and training. I run talent, HR, probably our platform initiative and several other areas. The CEO run sales and marketing, engineering and finance. Despite my accounting background, in our case, the CEO runs finance as well.

You had an accounting background. Did the CEO have an accounting or finance background or they decided to keep that as part of their focus?

When I joined Talkdesk, we had a twenty-minute conversation of what makes sense when it comes to scaling the company and this is how it stuck.

Let’s dive in and let’s do it. Talkdesk wasn’t the small startup in the garage or was it that?

No, Talkdesk was a small startup in a stuffy office in Mountain View. It was not very large when I joined it.

What is that part of your makeup that has you joining one of your first early stage company working out of a warehouse and then joining Talkdesk as a small entrepreneurial startup? What is that part of your DNA that makes that either exciting or interesting versus getting into a bigger organization like Salesforce right across the street?

I skipped some points in a way. When I joined top management and helped build this company, I was 23 or 24 and for me, it was great to work out of this warehouse. It was pretty fancy. I came from the military and lived in tents and so this was exciting for me. It was very different. It was touching technology, working with Mac computers that were fancy back then. It was very different. This company ended up being acquired by SAP. I did spend six years at SAP as a senior VP and GM. I had a chance to live life and fly over the world in business class and go to fancy hotels, have a driver pick me up and everything else that the senior role in a large organization affords to.

I didn’t get the same level of excitement that you get in a small fast-moving startup. When I left SAP, my son asked me, “Why would you do that? They paid you a lot of money.” He was ten back then. I said, “They paid me a lot of money but it’s not enough.” Part of me is interested in the building and the novelty of different challenges every day. Solving a new problem every day and challenging the status quo rather than maintaining your status quo. A lot of what drives me is how can you take something that is still small and not necessarily fully shaped and shape it. Even during my time at SAP, this was my role because I was leading a whole new area at SAP, the SMB space. Once the SMB space became mainstream, it wasn’t exciting anymore.

That’s part of what makes the COO role fun as well is we do get to see the fruits of our labor. We’re in that operational make it happen role. We get to help the CEO either design or implement the vision because we’re in that leadership role, our work gets used. How have you continued to grow your skill set over the years?

You learn through seeing a problem, solving problems, making mistakes and not ignoring mistakes. The only real advice I have to people is to be honest with the mistakes you’re making. I’m looking back at Talkdesk and I’m in tech for over twenty years. I think of my time at Talkdesk as probably one of the top three learning and growth opportunities I had in my career because of how fast this company grew. You look back and ask yourself, “Where do I grow?” Even when you’re 40, 50 or 60, you have to continue to ask this question, “How can I continue to grow? What will challenge me?” What challenges you are taking a lot of action and doing a lot of things because when you do things, you get somehow good results and horrible results. If you don’t ignore the outcomes, you can learn from it. The person you hired and was a wrong hire and how you dealt with it and the person you hired was a phenomenal hire and how you promote this person, give him latitude. A lot of my learning and growth was just paying attention to my mistakes and not ignoring them and not blaming them on somebody else.

SIC 10 | Talkdesk

Talkdesk: The whole business climate is changing fast. What we do fifteen years ago do not work anymore today.


You’re pretty introspective as well then.

I try to. We all have self-story. It’s not common and memories are funny this way. If you only tell your self-story, you’ll never grow. If you’re always going to be the person to say, “Trust me, I’ve done it before,” you’re never going to grow because what you’ve done before is irrelevant. The world is changing all the time. It sounds like a cliché but it’s true. If the world is changing all the time and you have done it before and this is your claim to fame, then you are not growing that much. You’re probably building what needs to be built fifteen years ago but not what you need to do now.

On talking about what we need to do now versus fifteen years ago, the whole business climate, the business world, all the technology tools that are coming out, it’s happening faster and faster it seems. What are you doing for the organization to ensure that you guys stay ahead of the curve on everything?

The first thing that you need to do is be part of this change. My father is almost 90 years old and when Google launched Google Docs, he was probably 80. He sends me some of my financial information, he was managing for me back in Israel, on a Google Docs and see how cool it is. We can collaborate on it. An 80-year-old was one of the earliest adopters of Google Docs and was enjoying the fact that we can collaborate across the continent on a financial spreadsheet. I’m seeing myself and trying to be the same person. When the scooters came in San Francisco, I jumped with them and gave it a try. When they had this JUMP bicycle, I tried to go around with them. With this new technology, I try to use them as well because without immersing yourself in everything new, you will never be able to use it. You can’t look at the world and say, “It’s changing. I’m too old for that. It’s not for me. It’s for kids.”

Snapchat is for kids. There is something to learn about Snapchat even in the enterprise. There’s something to learn from the blockchain. All these new technologies are somewhat interesting even if they’re only tangential. Part of what I’m trying to do is immerse myself in everything new and hang out with people of all ages. Some of my friends are twenty years younger than me. Some of them are twenty years older than me. Being around people of all ages and all areas is helpful. The first and the most important part of it is to be part of the technological change and understand it rather than saying, “This is for the new company.” When you look at older companies and they developed slow, a lot of it is because they think that their magic sauce or secret sauce is about the technology they built their product on or about what customers wanted ten years ago and not about this changing market. Keep thinking about it. Keep being part of it. Keep trying to be part of this world, to me is the best thing I could do to bring back innovation to the company.

When you’re so open to innovation and change and what’s happening and what’s new and you’re exploring, how are you staying in the day-to-day? Do you devote a certain portion of your time to focusing on operations and execution and some around the future of where we’re going? Is thinking about the future and change part of your view of strategy for the company? Walk us through your mindset around that.

It’s more of the latter. I don’t claim to be your typical operational person that organize their day into blocks of one hour. I wish I could, but my brain doesn’t work this way. My day is more of a mash-up of many different things. I try to focus on what’s most important in a given time. Vision strategy happens naturally when you do everything else. My role puts me in a position of meeting a lot of customers. I have a lot of conversation both with prospects and customers and each one of them teaches you different things. The prospects teach you about what they want and how they see the future. The customers give you a good view of what you do well and what you don’t and how can you help them.

In my specific role, I call customer service a lot. Ask my wife, I volunteer to take care of our own customer service calls because I want to experience how it feels as a customer to call 50 different companies and get service from them. I use a lot of our customer’s products so I can at least call their customer service and see how it goes. I have a good icebreaker with my customers. All this mash-up helps creates this view of what the company needs to go. I spent a lot of time with the CEO and understood his vision as well. He started a company. He got it to where it is. His vision is critical and this is what’s unique about companies.

It’s not necessarily the hired help. It’s the vision that started the company. It still needs to live within and all this create a mash-up of what I think the company’s strategy is. Maybe another way to answer that is that when you hire good people and all the areas I’m running are good leaders. The operation part becomes less taxing and you can focus on helping them make some of the harder decisions. Some of the areas that they’re not sure about but you don’t have to manage their day-to-day. The biggest gift you can get from your leadership team is the gift of not needing to manage their day-to-day.

First off, how do you stay in sync with the CEO on his vision? Are there systems you use for that? Is there meeting rhythms you have? How do you get on the same page and stay on the same page? Secondly, how do you try to free up time and do you work on helping your direct reports free up their time?

There’s not much you can learn from the way I interact with Tiago here because he is different from anybody else that I know. He’s young. He’s 31 years old. A lot of communication is various forms of chats. We probably chat 50 times a day and also weird hours of day and night. We meet a lot informally. We don’t have a lot of organized one-on-one. We’ll grab lunch here or take a walk here or go for a drink or something socialize together. We never socialize and don’t think about work even when we go have a drink or go out sometime when we travel. It’s a mix of talking about work and personal stuff and get the stress built that is essential for this type of work.

The general advice here is you have to communicate with your CEO the way he or she wants to communicate with. You cannot say, “I have to have the one-on-one Monday or Friday.” I heard this is what Sheryl and Mark Zuckerberg are doing. Everyone has different cadence based on how they think about things. In our cadence is much more continuous than formal meetings at the beginning of every week. To me, part of my trick too is there are certain topics I’ll bring in chat, certain topics I’ll bring over the phone, there are certain topics I’ll bring in person. Knowing the person you work with well helps me decide which topics I want to discuss right now because they’re urgent and which topics can wait two or three weeks for the right time for an in-person conversation. Being patient is a good skill for a COO.

Are you guys operating under the same office space or are you in different offices or different cities?

We’re in the same office space. The travel schedule we sometimes don’t see other for a month to a month and a half where we don’t overlap for a long period of time, but we work on the same office, and we try to spend a good amount of time together.

One of my mantras over the years has been that the leader’s job is to grow people. I’ve always believed that the more that we grow our direct reports, and the more we help them grow their direct reports in terms of growing their operational skills, their leadership skills, any of the soft skills of management, the faster the company will accelerate. Can you give me any of your insights on growing people? Secondly, what mantras do you operate by or do keep front of mind?

To me the most important for any leader that’s worth their pay is they want to have a sense of agency. They want to be the one driving their unit and making decisions. If you go back to how I learned which is doing and making mistakes. You can’t learn if you only execute someone else’s ideas because they’re never your mistakes. Your mistakes are in the way you carried the operation but not necessarily and decision led to it. It is the way I learned. It’s the way I want my direct reports to learn. I honestly try to be as little as possible in their way and give them as much freedom as possible. I often tell them, “Don’t listen to me,” or “Here’s my opinion but call it BS at any time because I’m not sure I’m right.” I encourage that because I don’t want people to think that if I said something, it’s more important than what they said. In some cases we formalize it. For example, in hiring process, in what we call tribals, we talk by seniority. The more senior people would talk last.

If I don’t like someone, we don’t bias everybody else. In some other cases you will have an opinion. Nobody else will talk and you want to make sure that you’re challenged. Part of my trick here is to say, “I think I may be wrong. Please don’t take it as gospel but here’s what I think. Do you think differently or call me BS if you think I’m BSing?” Sometimes people do that. Going back, if you don’t give people freedom then you’re not going to get much out of them, and you don’t need to hire very senior people. You want to run the company with 100, 200 people and they’re going to carry your decisions. You can hire pretty junior people, they may love it. If you hire senior people who want to grow, part of growing is doing, deciding and making your own mistakes and learn from them.

That’s a huge lesson. Many people try to hire senior people and they don’t treat them like senior people at all. You touched on something that I covered in my book Meetings Suck. I was trying to codify how companies can run great meetings and one of the systems I put in there was that leaders should speak last. You even touched on that. You don’t want to sway the group. You don’t want your comments to steer them in a direction. It’s a powerful lesson for sure.

You also need to meet to learn yourself. When you have a stronger personality and many people in this area have a strong personality and strong opinions, you’re not going to change. You’re not going to become someone else that doesn’t have an opinion or always speak with question marks. I tried to do that but it’s more of a tactic than a strategy. I have strong opinions about things and Tiago, my CEO, has a strong opinion about things and if you want to allow others to have opinions as well, you can’t hide your opinions but you can handicap them by saying, “I may be wrong. It may not be true. I didn’t do the homework. I don’t have the research to support it.” You leave a lot of openings for people to contradict you but also look for people that will. If you’re a strong personality, you need to look for other people with strong personalities, so they feel comfortable challenging you. If you are a strong personality and you hire a bunch of yes people, nobody’s ever going to challenge you. Even if you make all the comments in the world and say, “Challenge me,” if you don’t have strong people around you, they’re not going to challenge you.

We started an organization called the COO Alliance which is the only network of its kind in the world for seconds-in-command. One of our members was rolling his eyes thinking about his CEO and said, “He didn’t give me a chance to chime in. It’s his way or the highway.” I’m starting to see a fracture there that this guy needs to get something changing or he’s going to lose a strong hire as well. With your growth in terms of the hiring of people, you mentioned that you want people that are going to challenge you and be strong leaders. How do you identify strong leaders in the interview process or how do you even go ahead of the interview process in the job postings and the recruiting? How do you recruit strong leaders?

SIC 10 | Talkdesk

Talkdesk: If you hire a bunch of “yes” people, nobody’s ever going to challenge you.


I wish I had the right answers to that then I will never make hiring mistakes ever again. I discovered something interesting about myself. The rare cases when I know the person sitting in front of me is the right person. It’s rare. It happens twice a year maybe. In these cases, I was never wrong. When I feel super strong about someone, I’m yet to be wrong but it happens rarely. I’m also still hiring people that become strong that I didn’t feel this way from the beginning. The first thing I learned is that when I feel strongly about someone, I usually don’t make a mistake and this person should be hired. I don’t know why. What is this feeling? How did it happen? I think it’s a combination of seeing someone driven that know what they want, understand how to get it done and can describe how they’ve done before. It’s also something which I cannot explain.

I can go back and say here are all the people I felt that they are the right people but there’s not much in common between them. The different genders, different races, different steps and stages in their career, their different roles, there’s something about them and maybe it’s an experience that made me feel very strongly about them. When it comes to the vast majority, I think there are things you have to do and the first one is don’t only trust yourself. Open the interview process to as many people as possible in the organization. Make sure they know what you’re looking for. Make sure they know you. It’s not useful to bring someone that just joined two weeks ago and ask them to participate in an interview process if they don’t know what the company wants and what you want and do a lot of back-channel reference check.

Don’t rely on HR to do reference checks for you. Don’t rely on the references the candidate gives you. Do a lot of reference checks and do them yourself. Ask the question that you are worried about. Not too long ago I interviewed a senior leader and I ended up not hiring him. There are several question marks that I had during the interview. I’ve spent probably five hours reaching out to different people, having long half hour conversations, until I was able to validate in this case, that I was right, and my instinct and the person was not truthful in the interview process. I had to spend this time, otherwise, I would have had the wrong candidate.

I know you’ve got a few but I think you may have touched on one of the core reasons why you’re successful and it’s you’re interviewing, hiring and reference check process. Even though you said you wish you were right more often, or had it all figured out, the fact that you spend that much time, you’re one of only a few senior leaders I’ve ever spoken to and I’m very much like you. I did twelve reference checks on a guy, Christopher Bennett, years ago. Seven persons and five businesses to people he didn’t give me the names. I dug up and then made him get me their contact info and it was because my spider senses were saying there’s no way this kid at 23 years old could be as good as he said. He was almost like a renaissance man. It seems like my spider senses are saying he is, but if he is that good, people must hate him and I just needed to know.

It turns out everybody I spoke to said the kid was amazing. One of them was his boss at the time. He said, “You’ve got my best guy,” and Christopher Bennett ended up being one of the core reasons why 1-800-GOT-JUNK? became what it was. He was a huge cultural hire for us. It was the reference checks that made it okay to go in and make that hire. Trusting your gut, I’m the same. I’ve had the only probably three people that I can remember in my career, David Crombie, Mark Rubin and maybe Christopher Bennett that I knew at my gut level out of hundreds that I’ve hired that they’re going to be amazing. You just know. Do you trust your gut in other decisions in the business or do you operate more under Google? “I don’t care what you think, I need to know what the data is.”

It’s a little bit of both. I trust my gut a lot. As a senior leader, when you’re a little far away from the day-to-day data, what I often ask people is, “Don’t try to out gut me. My gut will win.” The COO’s gut will win because we are more senior, we’re more experienced. Tiago started the company. His gut will win every time. You come with data and you come with research and then you can persuade my gut that I’m wrong. I like to look at data. I think they’re super important. I always say product meeting start with a data, start with a research, start with how you formed your opinion because if you just have an opinion, my opinion will win. Part of it is knowing that you need to challenge your gut because it’s going to be right in many cases, but your gut is a reflection of your past.

It’s our reflection of the future. What we call gut is our total experiences. It’s a very normal thing and if we remember that our gut is the reflection of the past and all of the future. We need to allow ourselves to keep challenging it because otherwise, we’re going to continue doing the same things over and over again. That’s why I’m asking to keep challenging me, keep bringing the data, keep showing me something else and I will be convinced. Don’t tell me my gut feels this because it’s a very hard argument to win with somebody more senior than you.

That’s an interesting perspective that our gut is a reflection. I’ve always looked at the gut as our human computer and the gut is a reflection of our past. If we’re building a company into the future, everything, the rules all changed. The use of technology change, the way businesses are running, the speed of change. The people that were good working with us ten years ago probably aren’t going to be as good or they need to be very different going forward.

Part of the appeal for me of joining a company where back at the time the founder and CEO was under 30. He did pretty well growing the company until I joined, was there’s something that he does and he knows that I don’t. Maybe it’s the years between us. Maybe he came from Portugal and come from a different culture. Maybe it’s the composition of his character, but it’s something he knows and he does and I don’t. In fact, I was going to tell him, “You’re wrong. I’m right because I’m experienced,” then I’m going to build the past. Part of building the future is collaborating with people who think differently than you. They may be wrong because it doesn’t mean your gut is right probably 80% of the time.

What’s worked in the past is probably going to work in the future 80% of the time, but you always need to seek for the 20% because the 80%, what’s right is right. There are some basic things that will always be true. If you’re out of money, your company is going to cease from operating. This is true. There’s no need to argue it. It was true in the past. It will be true in the future. There are things that are not as black and white. For this you need to work with people who challenge you. It doesn’t matter if they’re the founders or a new employee that joined. Somebody will always be able to tell you something that the onus of proving it is higher when you’re more junior or less experienced.

That’s interesting and I love that you’re making people think and debate it as well because that’s growing your skill sets too. This is a random question that came to me. It’s related to the organization as a whole, the org chart and structure. I was thinking about Zappos and this organizational structure that Tony Hsieh tried to implement a few years ago with a flat organization, no titles. What’s your org chart look like? How do you operate with an organizational structure and titles etc.?

We operate in an environment where a lot of people care about titles. Zappos had a unique opportunity to hire in a place that didn’t have a deep-rooted culture of titles: VPs, EVPs, RVPs and so on. When you bring in people from Salesforce, LinkedIn and companies in the Valley, they expect to have titles. We’re not very different. We have VPs here. We have directors. We try not to have too many layers. For us, a VP is someone who can own an area. An SVP is someone who would own multiple areas. We have only one C-level person or two C-level people. COO, myself and we try to keep it as such. We’re trying not to create inflation of titles. Honestly, I do understand that at some point in time, and this is what Salesforce did in “05, “06, you have to create more layers because people want to see growth.

Especially now, people want to see every year or two a promotion and career growth. If you don’t have enough layer that can demonstrate that it’s only about money. It’s about public recognition. You’re going to end up losing some good people that want to see this career progression. We’re not that religious about that. I think this being flat in titles but also being flat in communication and the way to work directly with people. I will tell you this company if the CEO wants to run an idea by a product manager, he does it. We don’t care that there are two or three layers between the CEO and the product manager and nobody takes it personally. Why was I not cc’d on this email? You have a question ask, if you want to run an idea, do it. It doesn’t make the company less effective.

Good for you. You’re avoiding all the bureaucracy and the pain in the ass but still giving structure that people need day-to-day too. Humans still want to know where they fit and where they line up. I completely agree on the need for titles and for roles as people are moving up in the organization too. How are you guys competing in the Bay Area? You’re in a very competitive environment. In the last few years there’s been a lot of talk about companies even leaving the Bay Area because it’s so hard to keep talent, let alone get it. How are you guys competing and winning in the war on talent? What are you doing that’s working well for you?

I have to acknowledge that this is an area that we don’t have a good answer. Talkdesk has three main locations. We have most of our R&D is in Portugal, in Lisbon and Porto. This is where the company started, where the first engineers came from. One of the advantages we have, and this has been in Porto, we are one of the top three, four startups that people want to join. The war on talent there, because the tech industry is newer, it’s simpler for us. We build a strong brand of a company with advanced technology, with great challenges for engineers. Almost every engineering in Lisbon and Porto were interviewed at Talkdesk. One big year for us which is R&D and some of the other areas is covered by the fact that we ended up starting the company in a smaller location and became one of the top three startups in the country. It gives us this amazing access to talent and the ability to hire and retain good engineers from an education perspective and from experience perspective are very similar to the one we would be able to hire here, if not better. We have the first pick on most every engineer.

We have a second location in Salt Lake City and the reason we have a location there is one of our biggest competitors in contact is there. A lot of the company that was acquired a few years ago, a lot of people are leaving the company now and it was an opportunity for us to hire good talent in an area that cares about the problems that we’re solving, which is another very important piece. Do you join a company because it cares about the mission or just a cool tech company that grows fast anymore than your resume? A lot of the people we hire in Salt Lake care about the mission. They want to build a better customer service platform and they care about our mission and therefore they join. In San Francisco, which I kept last is much more challenging. There is a combination of people that want to join because they care about our mission and they care about what we do. A lot of the people join because they want a great name on their resume. It’s an objective problem that is hard to resolve.

In conversations with other CEOs, COOs and investors, I actually say, “I think we need to acknowledge that in San Francisco an average tenure for an employee might be between a year and a half to two.” The great ones that got multiple career promotions will maybe stay up to three years. We’re looking at different job markets where you will have people coming and going in the course of a couple of years. It needs to impact training, onboarding and other hiring strategies because the market is changing. I don’t blame anyone here for a twenty-some years old employee that maybe graduated a couple of years ago. It’s a Disneyland of opportunities and all of them look very similar. Think of somebody at Disneyland, they get to decide which ride they’ll go first. A little of it is because of that. It’s a great time. The economy’s booming. San Francisco’s economy is booming, and people have a lot of opportunities and it’s hard for them to choose.

You’re right and it’s smart to understand that as an organization too, we have to attract people. We’ve got to try to retain people and also have reasonable ideas on how long they’re going to stay. I’m surprised you even said a year and a half to two. I probably would have gone like nine months to eighteen months in the Bay Area, but it’s nice to hear that they are staying a little bit longer. I want to wrap up with one question and it’s not a framed question that I ask everybody. I’m just curious for you, if you were to give advice to someone going into a second-in-command role for the first time, regardless of the size of the organization, what would be the one big lesson that you would pass on?

Focus on number one and the number one, in this case, is making sure that there’s something about this person you deeply respect. If you come to an organization and you think you’re better than the founder CEO in any way you can imagine, this is a big red flag, don’t join. This person has to have at least one towering strength that you respect, you want to learn from and you want to work with. It’s clear that many of the seconds-in-command are going to be better in many other things than the founder, CEO. If you don’t have one thing you respect about this person, it’s not going to work. You’re going to continue fighting because you think you’re better in everything than this person. If there’s one thing, I will look at this one thing and ask myself, “Do l respect this person? Is there something special about this person that I want to learn from?” If not, just walk. It’s never going to work.

I was doing an interview with Forbes magazine with the print edition about a few months ago on an article about female COOs. The interviewer said, “Most COOs, most seconds-in-command obviously want to be CEO someday,” I was like, “Not really.” From the group that I’ve seen, it feels like an awful lot of the seconds-in-command are happy being in that role and they don’t ever want to be the entrepreneur or the CEO. Is that similar for you or do you have aspirations to move into a CEO role someday once you’ve continued to build up Talkdesk?

SIC 10 | Talkdesk

Talkdesk: There’s something special about being number one that you cannot get by being number two. That is being able to fully control or influence the culture and the spirit of the company.


I’ve been in leadership positions where I was the leader and I’ve been number two. I’ve experienced this even in the army as a company commander but before that as a deputy company commander and I enjoy both. There’s something special about being number one that you cannot get by being number two. The most important part of being number one to me is being able to fully control or fully influence the culture and the spirit of the company. This is something that you cannot do as number two and I often miss it. I say that I will probably feel or probably maybe be again a COO and I tend to flex my personality and look for what’s the right opportunity for me at any specific moment. I do like being number one and I do like being number two with the right number one.

It sounds like you’ve got a great number one that you’re working with and also a great path ahead of you at Talkdesk as well. Gadi Shamia, thank you sincerely for the time that you spent and for some of the insights you gave us.

It was great talking with you, and I just saw 1-800-GOT-JUNK? truck driving under me as we’re speaking.

I actually left 1-800-GOT-JUNK? many years ago. I left as the COO there and that was a long time past but that was a great part of my career for sure. Gadi, thanks very much for your time. I appreciate it.

Thank you.

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About Gadi Shamia

SIC 10 | TalkdeskOver 20 years of leadership roles in enterprise software and 13 years in SaaS. Most recently I took Talkdesk from a seed stage to a Unicorn as COO and helped architect and execute its 20X growth in people and revenue.

The first startup I co-founded was acquired by SAP and is now SAP’s core ERP + CRM offering for SMBs, and > half a billion dollars a year global business. Additional leadership roles at SAP (Sr. VP/GM), Adobe (Operations, M&A integration), ReachLocal (President & General Manager, throughout IPO).

Boards roles at EchoSign (acquired by Adobe), Intacct (acquired by Sage for $850M) and Talkdesk.


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