Jan 4, 2023 | 4 min read

Greg Carter

Podcast #196 Customer Success


Customer Success

In this episode, Ken Forster speaks with Greg Carter, former Chief Customer Officer at Digi and Head of Business Operations at Tive.

Greg has worked in the high-tech sector for almost 30 years, primarily emphasizing customer leadership in startups. He specializes in building teams, systems, and processes that can keep up with the size of high-growth businesses, emphasizing operations and customer success. Greg is an authority on hardware and SaaS, and he has deployed more than a million devices to more than 100,000 locations. He is a former member of the armed forces and serves on the advisory board for Youtilligent.


Discussion Points:

  • What would you consider your "Digital Thread"?
  • You've had a long track record of customer success roles leading up to being named Chief Customer Officer at SmartSense by Digi. If you had to summarize that time before Digi into three learnings relative to Customer Success, what would they be?
  • I'd like to drill down on your time with SmartSense. Can you tell us about the company and your remit as Chief Customer Officer?
  • Digi has been a benchmark in the IoT space due to its focus on recurring revenue models - a wide chasm to cross from a traditional hardware focus. What did SmartSense bring Digi that became the catalyst for this change?
  • Digi crossed the recurring revenue chasm, posting spectacular market returns. Yet, for the leadership path, they've so well demonstrated, their IoT hardware peers have not been able to emulate this effectively. Why do you think that is?
  • You eventually left Digi to join Tive, a hot startup in the Supply Chain space. Your focus there has been Head of Business Operations. What was your remit at Tive, and what are some of the wins of which you are most proud?
  • Across this whole journey, you've consistently been a leader in Customer Success. You've specifically mentioned about this being a new world of customer service where companies that get it are partners, not vendors. What is this new bar of customer experience?
  • What trends are you watching these days?
  • So, knowing that you've just left Tive, what's next?
  • In closing, where do you find your personal inspiration? (i.e., book recommendations, articles, podcasts, people, etc.)



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View Transcript



Ken: Today, I'm pleased to host Greg Carter, former Chief Customer Officer at Digi and Head of Business Operations at Tive. Greg has spent nearly 30 years in the high-tech industry focusing on customer leadership and startups. He specializes in creating customer success and operations systems, processes, and teams to help scale high-growth companies. Greg is a hardware and SaaS expert and has deployed more than a million devices to over 100,000 locations. He sits on the board of advisors for Youtiligent and is an Armed Forces veteran. Greg, welcome to our Digital Thread podcast, and thank you for your service.



Greg: Thank you again for having me. I look forward to this discussion.



Ken: As well, as well. We call this the Digital Thread podcast; of course, we want to talk about your digital thread, in other words, the one or more thematic threads that define your digital industry journey.



Greg: I took a little time to think about this. The one thematical thread that defines my career and my digital journey, for that matter, would be the evolution of technology and customer service. When I started right out of college, I am a bit embarrassed to admit it, but email was just getting popular- so when customers wanted to ask a question, their only option was to call by phone. If they were lucky, a toll-free number was associated with it. This was a very personal exchange and very high touch. Fast forward 30 years, and you're almost lucky to find a phone number on a website, as many other technologies have come into the market. The real trick, or magic, is how companies can stay efficient with their customer success departments while delivering what I consider 'wow experiences.'



Ken: It's an interesting point, especially in the age of connected devices. Because in the past, customer success was largely tied to deployment. But in some cases, you're talking about devices now, in essence, reporting their service information as well; we've invested in a company that looks at this exact space, making it a very interesting space, as you say, the evolution in there as well. I know you've had a track record of customer success roles leading up to being named Chief Customer Officer at SmartSense by Digi. If you had to summarize that time before Digi into three learnings relative to customer success, what would those be?



Greg: That's a great question. Limiting it to three is hard, but I'll give it a shot here. The first learning is realizing that someone took a bet on you, and that's the way that I look at sales. Whenever a customer signs on the dotted line, or electronic signature nowadays, and agrees to purchase your product or services, someone's job can be on the line. Sometimes, these contracts are multi-year in multi-million-dollar contracts. I'll never forget when I worked at a startup called TempAlert- temperature sensors to a very major player in the retail pharmacy market who took a gamble on a nine-person company in a leaky basement in Boston to roll out every single one of their stores. They had 11,000 locations. So I knew that person that signed off, and he took a risk on my customer success team and me.


One mission after that- and I was to make that person look great. He could call anytime, day or night, and we would always answer and, even more importantly, respond. I remember in this learning that someone took a risk on you, and you want to make sure that you make that person look good. The second learning is that- and this is my interpretation, it's that customers want partners, not vendors. Customers don't want to keep finding new products to address the same needs. They want a partner to work with and grow with them. They also want transparency, which is a little uncomfortable for some. Still, it's okay to show that your organization is not perfect. Own up when there are issues and move on. You'll gain a lot more credibility. I also believe that customers and partners are equal at the table with mutual respect. With that in mind, saying 'no' is not bad. It's a hard thing, but it's not a bad thing. A great example, at least with my past, is I come from a lot of hardware and software where customers want to make a custom, whatever it might be. I coach my customers to stay on the path where the main development will be; enabling customers to go and do a one-off is a road to increase my incredible customer dissatisfaction and frustration. Then I have several more, but the last out of the three is higher on two things only, and my perspective, yet again, is aptitude and attitude. I've had a great previous CIO mentor at RSA. They embedded this into me.


Without a great team behind them, there's no impact on a customer success leader. Honestly, some of the best people I've hired in my career- and I've had a long career of hiring people, did not have outstanding pedigrees or experience. I typically hire people that are go-getters; they're very humble. Then you empower them to figure out things on their own, and those people provide truly exceptional customer experience. In my previous company alone and the last company I was with, the person who ran customer service was a previous barista. The person running all our customer success worked as a major league scout at a baseball team. This philosophy matures as your company climbs up the maturity curve. But once again, just hiring on aptitude and attitude has been a great aspect for me to build great customer success teams.



Ken: Great points. I always like making sure I have three good descriptors there. I call it perspectives, making your client look good. Partnership- customers want partners, not vendors and people. Hire on aptitude and attitude. I like the way that you've laid that out. Let's drill down on your time with SmartSense by Digi. Please tell us about the company and your remit as Chief Customer Officer.



Greg: I'm a huge fan of SmartSense. I think that they have great products and services. They have experienced leaders with exceptional vision, and I was lucky to work side-by-side with a lot of them. I spoke about this before, but I was hired as employee number nine at a temperature monitoring company called TempAlert to run their customer success and supply chain teams. I started in the supply chain about nine years ago. I was also incredibly fortunate to have a VP of Program Management start the same day as me. This guy could make it happen, along with what I consider an unbelievable Chief Customer Officer and a great CEO. One month after I started, we started rolling out one of the largest retail pharmacies. It's important to note that we had no playbooks, no distribution, and too few team members in my mind. Of course, the thing hanging over your head was the timeline. Over the next 18 months that I was at TempAlert, we rolled out about 30,000 locations as we continued to win, in our minds, the large retail pharmacy business. It's truly amazing what a team could do with a common goal and these unbelievable pressures around it. I'm still shocked at what we accomplished. At the same time, Digi took notice of the inroads we were making and had already purchased three other small, similar companies. They were in the temperature monitoring space.


Digi also acquired us. Like in most acquisitions, my CCO and my CEO left the organization. The former COO of Digi International became the president of this new division made out of these four companies called SmartSense. This president asked me to work with the other three companies to galvanize; all the other customer success teams were disparate a little bit, as also their supply chains. I was working directly with the CTO of TempAlert, and his job was to consolidate all the platforms and products. We had well over a hundred a platform and products at that time. It's not an easy process, but at the end of the day, after everything was said and done, I think that we are the best-in-class temperature monitoring and task solution that can be easy- and that's a tough thing, easily deployed to industries. Our main thing was retail pharmacies, but we also got into hospitals, labs, groceries, restaurants, and transportation. When I moved on from that area, we had a solid playbook which we had none at the beginning. We had a supportive organizational chart that enabled us to roll out about 80,000 locations and over a million centers. The best part of that story is our extremely low churn and high customer satisfaction during this process. This is all made possible by SmartSense team members making superhuman efforts. Talking about being on the shoulders of giants, I consider myself very lucky.



Ken: Digi has been a benchmark in the IoT space due to its focus on recurring revenue models, which is a wide chasm to cross from a traditional hardware focus. What did SmartSense bring to Digi that became the catalyst for this change?



Greg: When TempAlert was purchased, Digi had a small revenue or recurring revenue stream when they bought us, but they knew that that was the direction they wanted to go to and to move a little bit more from a one-time hardware company or OEM company. I had the benefit of working with Digi's CEO and CFO, and they appreciated the simplicity of our SaaS billing model. TempAlert could bill very quickly because we could stand up our product fast and with high quality. One of the biggest areas that we looked at, or the biggest metrics that we focused on, was time-to-value. Typically for a non-enterprise, we can get you up and running within a week of shipping the product. That's our quick billing process. This helped Digi look at our model, take it, and move it into the greater Digi International.



Ken: Digi crossed the recurring revenue chasm and posted notable market returns. Yet, for the leadership path they've so well demonstrated, as I look at their IoT hardware peers, they seem to have found it difficult to emulate what Digi has done effectively. Why do you think that is?



Greg: Honestly, I think it comes down to leadership. The senior leadership at Digi has been working on a recurring approach for many years, and it comes down to a lot of learnings over those years. Working with them and being side-by-side with them, I find them incredibly meticulous in how they either build or buy. They've got a great track record of mergers and acquisitions. I think that's why they've been crossing that particular chasm. The stock reflects that as well.



Ken: I know you eventually left Digi to join Tive, quite a hot startup in the supply chain space. Your focus area has been Head of Business Operations. What is your remit at Tive, and what were some of the wins you were most proud of?



Greg: Let me give you a little background there. My president at SmartSense was retiring, and I felt I had accomplished a lot. I've also been working with an exceptional customer success manager for the last three years at SmartSense, so I felt confident moving on. Tive is a company that created a simple and effective device about the size of a deck of cards that you can put on anything that you want to track where it is and how it is. It's as easy as pushing a button on the device. I was asked to head up their business operations team and, hopefully, make Tive much more efficient. I can give you a rundown on some of my fun wins there. My fun wins included being part of the acquisition team that bought a Norway company called TagCenters which made a cost-effective, almost wafer-thin data logger. This incredible technology truly complemented Tive's products. We opened up new markets as a much lower-cost data logger. Wonderful people up in Norway. The next one was that I took a step back and revamped the objective and key results process at Tive.


I worked with the CEO; he was a great CEO. I created a limited amount of yearly objectives. Then I worked with each one of the heads of the departments to laser focus on key results based on the objectives that I laid out with the CEO in small chunks of 90-day increments. I found that to be incredibly effective. Then another fun project that I worked on was quote-to-cash. These are three little words, but boy, they mean a lot. Tive purchased several leading systems like customer management systems and financial systems. I led a team mainly of engineers that worked to connect them, so all the orders could easily go through each system automatically, drastically reducing the level of effort per order and increasing the quality and visibility of our systems. The sales team typically wrestled with a bunch of overhead beforehand; now, they ride the rails of their CRM, which goes directly into billing. Believe it or not, this is one of the holy grails of effective business operations. I'll sneak in a last one, Ken, where I took time and found a new headquarters for Tive. They were moving out of a smaller place, growing, and busting at the seams. We moved into a state-of-the-art place right in Boston. I'm very proud of that overall, but important to know that Tive is an incredibly innovative company with such a talented team. Keep your eyes out for them; they're going to crush it.



Ken: Surely. You've mentioned right up front about consistently being a leader in customer success and being quite passionate about it. You were quoted upfront about "A new world of customer service where companies that get it are partners, not vendors." What is this new bar of customer experience?



Greg: I always love to tell a story, Ken. I read a customer success book, and the author was talking about when he called a pizza company. I'll get it roughly on this, but they say something like, "Hello, Tom. Would you like us to make another pie for you tonight?" And Tom says, "Yes." And the pizza company says something like, "Hey, would you like to order the same five pizzas that you did last time?" He got three kinds of cheese and two pepperonis. And Tom says something like, "Oh, no, no. That was for a birthday party. I just need one cheese and one pepperoni." And the pizza place says, "Hey, do you want them the same way? Light sauce and slightly overdone?" And Tom says, "Yes." And they say, "Do you want us to deliver to 123 Ocean Ave?" And Tom, yet again, says yes. And it goes, "Hey, we'll be there in 20 minutes." It went something like that. You can imagine this is what the world is contending with. Your customers are getting this level of service. This is from a pizza shop. You can imagine what they expect in the business world or enterprise. I think that support needs to be technology-enabled but very personalized. Think about this. I just read an article that says there are five generations in the workforce today, and they all want to interact differently.


From my perspective, you should layer in multi-channel support structures that can come in complete self-service- like everybody's used to going into an FAQ page and figuring out something for themselves. But now, those have technologies embedded in them that are Google-esque and can be SEO-oriented. Or some artificial intelligence chatbots that can help answer the questions immediately for the customer. I would keep the email channel open as well. You'd be amazed how many people still use this for non-critical questions or comments. Of course, I might be old school, but you should always have a phone number where people can call in and get support. It's important to know that you might take old things, but you can also put a new twist on them. For example, if your company sells software, you can put a chat icon inside that software. Imagine you're working on software, and you have a question. If customers get stuck in your software, they can click a magic button, and someone can help them right on the spot. There is a company that will learn callers' and support agents' personalities if you can imagine this. They'll review any voice, chat, or email conversations between that person, the customer, and the agent. Next time, they categorize that person's persona as A, and they match them up with the best persona on the support side, so you can imagine there would be a much better interaction. At the end of the day, it's our job as customer advocates to lessen the customer's effort and increase their value of the product and service overall.



Ken: I mentioned earlier that we did invest in a company in the space. It's called InSkill, and it's also a Boston-based company. But what's interesting is that in some sense, they want to give a customer service voice to intelligent products; think of smart sensors for home, like Nest, as an example, for home thermostats and the fact that the thermostat can inform quite a bit about its situation that can be added into a customer service response question. These devices are intelligent enough to report their condition; they can be tied right into like a voice response style system. It's an interesting space, there is a lot more coming, and certainly, you've hit some of the key things you want to do from a people perspective. But with the connected and intelligent devices, many more options will also come. On that topic, what trends are you watching these days?



Greg: Ken, here are just a few from my perspective. Customers want to still feel connected. Some concepts, like Domino's Pizza tracker, make you feel part of the experience. It might say something like, let's talk about mattresses. It might be like, "Hey, by the way, your mattress is being made by Greg, and Ken is packaging it up, and it might be delivered X, Y, and Z." People are now fully involved in the overall process of it and excited. I think making customers feel more connected is coming down the way. I get excited about the next one I'll tell you about; it's fun stuff like augmented reality and virtual reality, making it an immersive experience.


Now, people can go and virtually try on shoes or take a picture with their camera and see how furniture looks in their house. I'm very interested to see how that will be used from a post-sales support aspect. If you look at video support, that has gone through the roof. Between pre and post-pandemic, that's up 50%. I love this aspect of it; I talked about the phone aspect as being a high-touch medium. When it comes to port, this is a very high-touch medium overall. Organizationally, I'd like to mention that I'm seeing account managers, commonly called customer success managers, have a quota for net growth retention for an account.


I think this is important. I've seen those people taking more of that renewal approach and expanding that particular account. What this does is free up salespeople to hunt for new logos. Also, customers want personalized approaches; as I mentioned, the pizza store article said 66% of customers expect companies to understand their needs and expectations. Another aspect- and this is all over the place, is artificial intelligence. Chatbots habit as well, but it's not only helping customers, but it's also automating repeatable tasks that customer success organizations are leveraging. Money is being poured into customer experience departments, so believe me, you'll be behind if your company is not investing in it. We talked about the bar being raised, but it's being raised almost daily.



Ken: If you don't mind me putting you on the spot, who would you point to as a best-in-class example in terms of their customer success experience? Hopefully, it's something in the "IoT or technology space."



Greg: I'll give you a rustic one, then I'll give you a high-tech one. Casper, the mattress company I had a wonderful experience with them. It was something that I could easily go up there. I mean, obviously, the direct-to-consumer aspect of it. You could order the mattress, and they showed you where it is, and you could virtually try things out. They had a very easy exchange policy, they showed you when it was going to be shipped, and it shipped in a box, and you could easily set it up. I found the whole experience to be incredibly pleasant. Selfishly, I would look at it from a high-tech standpoint; I think SmartSense has got it nailed down overall. I haven't seen a company that can take something from a proof of concept or proof of value, and they can show the value exactly what the customer is looking for. They can do large rollouts to over 10,000 locations, but they can also do smaller locations. They can work with the customer to find out exactly what the success criteria is. They can stand up the product immediately after delivery, optimize the solution, and then work with the customers for long-term roadmap issues. Personally, I am very proud of where SmartSense is today because I have so much depth inside that organization.



Ken: Great, I appreciate the examples. I have heard many good things about Casper and have first-hand experience with SmartSense. Knowing that you've just left Tive, what's next?



Greg: This is a fun part for me. I'm in a lot of talks with companies that are serious about creating a world-class customer success organization and playbook. I love working for companies that focus on the how. I always look at what companies focus on the product, but I think more and more that 'how' is going to be the differentiator and how to me, a lot of times, is customer success in those organizations. I love joining a hyper-growth customer-centric company, and I've been fortunate that the last three of the four have had great exits. I love the messy middle overall; it's a lot of fun because of all the solvable problems, and I love working with people who believe anything can be done. My job is to find a company that wants to build a scalable customer success and operations department while wowing their customers.



Ken: I've got about 40 active portfolio companies that would be interested in what you just described, not to mention our own VC investors.



Greg: Good to know.



Ken: In closing, I'm curious. Where do you find your inspiration?



Greg: I'm a big reader and podcast person. Some of the great stuff that I've read is Tony Hsieh's book "Delivering Happiness," which I think is great. To go a little old school, I love "The Last Lecture." There are a ton of lessons that are inside there. I love the book "Extreme Ownership," and I listen to Jocko's podcast periodically. It's a little rough and tumbles around the edges, but its points are on point. It might be a shameless plug, but I love these podcasts that you do. You're almost getting up to 200 of these, and I think they give you a well-rounded perspective on a wide range of topics. I do a lot of trail running, so Audible is my go-to. I try to listen to about two to three books per month.



Ken: Excellent. Thank you for the shameless plug, which isn't so shameless. Now, it is well-rounded since we've interviewed you. Now, we're comprehensive. Greg, thank you for sharing this time and these insights with us today.



Greg: Thank you very much. It's been a pleasure being on here. As I said, this focuses on showing how important customer success is inside an organization. People remember experiences, and a great success team or customer success team makes a difference not only on the insurance side of the house but making and building long-term relationships overall. I appreciate the time.



Ken: No, I appreciate the overall conversation, but really, that good summary in the end there. This has been Greg Carter, startup enthusiast and Customer Success/ Operations Executive. Thank you for listening, and please join us for the next episode of our Digital Thread podcast series. Thank you, and have a great day. You've been listening to the Momenta Digital Thread podcast series. We hope you've enjoyed the discussion, and as always, we welcome your comments and suggestions. Please check our website at momenta.one for archived versions of podcasts, as well as resources to help with your digital industry journey. Thank you for listening.


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What inspires me?

I love reading and podcasts. I simply adore Tony Hsieh's book "Delivering Happiness."  The visionary CEO of Zappos explains how an emphasis on corporate culture can lead to unprecedented success."The Last Lecture"  by Randy Pausch is classic. "We cannot change the cards we are dealt, just how we play the hand." It contains many good lessons. I like "Extreme Ownership" and Jocko's podcast. In his book Jocko Willink an ex-Navy SEAL commander states that people must own everything in their world to succeed, and there is no one else to blame. Though rough, its points are good. I also love "The Digital Thread" podcasts—shameless plug. I think you get a well-rounded perspective on many topics with almost 200 of these. Last but not least, trail running makes Audible my go-to. I listen to two to three books per month.