Ep. 68 – Drips COO, Justin Miller

To have collective intelligence, a COO makes sure that there is effective communication and everyone is passing the information they need. In this episode, Drips COO Justin Miller narrates his background in the private equity space before coming to Drips and how he adjusted to their culture. He believes that transparency and communication make for a better company, as well as making sure employees are heard. Learn about conversations with consumers that lead to higher sales conversion, and of not being afraid of the uncomfortable.


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Justin Miller has many years of operating experience with a deep background in information technology management and infrastructure. Justin is the COO of Drips, a conversational texting platform where he’s responsible for growth through implementing relevant processes and systems. In addition, he’s responsible for the oversight of the company’s ongoing operations and procedures. Prior to his experience, Justin worked in Private Equity, primarily for technology-focused funds. He served a dual role in sourcing and doing due diligence as well as serving various CIO/COO operational roles in portfolio companies. Before his time in PE, Justin founded a technology service and consulting company. He managed IT infrastructure and operations for banks, hospitals, universities and other commercial businesses. Justin holds a Bachelor of Science in Business Administration from Northeastern University and an MBA from the University of California Irvine. Justin, welcome to the show.

I’m happy to be here.

Tell me a little bit about your experience in the PE space, what you pulled from that, and what you still use in Drips.

I love the PE space. As I’m sure you can relate, the experience is everything. For the most part, in a role like the operations role being in a PE space getting to work in a lot of our portfolio companies, you get a wealth of experience. I would be at three, four companies at a time helping out in different roles. The more people you interact with, the more problems you face, the more success and wins you have. That’s in systems, people, processes, and all that. It was great. Mostly, I was in technology focus. That’s how I got into PE. I came out of the tech world and had stalled in business understanding. I was able to blend those two together.

The funnel that I originally went to work for, they mostly invest in software companies. They took a heavy operational role. They liked my background and ability to evaluate a code level of what software we were buying. That was during the initial diligence phase and then they start putting me in some of these companies. The experiences you gain from those are ones that have helped me now, whether it be systems I’m putting in place, problems as they come up, employee problems, issues, what sales strategies you want to go with, customer problems. All of that are things that I’m able to pull on. Also, I have a network of people to talk to. If you want to go about, I have people you can go refer to when you come up with an issue.

How different were the portfolio companies when you were involved in the CIO/COO? Were they all starting to become similar or were they very different?

For the first one, they were somewhat similar. We did a lot of turnaround situations. Companies that may have stalled out a little bit, they all had that team if there needed to be some cleanup to go on. The similarity there is you’re trying to disrupt a lot of ingrained procedures, things that are already there and they aren’t working. The company is stalled out or stagnant. We see an opportunity for growth. A lot of them we tried to buy a platform and then build the box around it. Build that on smaller acquisitions and stuff as needed.

Each one had a unique issue. Some might be a great product but not a great sales team, “How do we get the sales and marketing going?” Likewise, some might have a great market presence, but the product is falling behind. They got complacent on their market presence. They didn’t develop the way they should so now we’ve got to attack the product feature. In terms of high-level that they were companies that need a little bit of a restart and they were technology was the same. I would say the problem we were facing or solving was a little different depending on each company.

How did you not get sucked into the operation so deeply that you’d be overwhelmed? It’s hard for most COOs to stay afloat when they’re running one company. When you’re active in three or four simultaneously, how did you manage your time and projects and not get too deep into it?

I’ll be frank, it’s something I struggled with. It’s more the, “Am I doing a good job?” piece. I wanted to be fair to all the companies. I do think I was able to handle it all. It’s like, “Could I be doing better if I had less going on or if I was able to focus on one of the other?” Fortunately, it was the time of my life when I didn’t have a whole lot of else going on. I could dedicate a lot of hours of the day and the weekends in it. Not to say that any COO doesn’t put in the extra hours by all means.

I also think it was the people that I was surrounded by. That was something that I’m always a big believer in like, “Who do you work alongside? Who you work with? Who do you work for?” and enabling them to help out. I’m making sure there are good communication and task management. A big thing for me, especially coming from the tech space is systems, IT and software systems that you use to enable what we’re trying to do. We’d use those for automation, information sharing and reporting. I was able to keep the pulse of three or four companies at a time if I needed to. For the most part, four was the max. I was trying to keep it more down to two or three. Maybe two main companies and the third was a half-time job that is needed. Organization and communication are the root of a lot of things.

What specifically do you learn there? You’d have to have been organized. You’d have to be on top of communication. What were their specific systems or things that you’ve pulled from that you utilize now?

One of the biggest things was what to focus on and that’s something that even here at Drips that’s come back to creep up and I don’t want to say bite me, but I realized, “I’ve gotten away from that a little bit.” Going back talking about the PE companies, there was a lot of change we wanted to make. You can see the list of stuff that you go in, you evaluate what’s going on and you say, “Here are the things you want to attack. Here’s all the stuff we want to do.” You lay it out and plan it out and, “I’m going to type this once you go and get it all done. I want to solve it all today, I want that fixed.” You dive into that piece but then you obviously have these day-to-day activities.

Things come up, you have problems with clients, employee issues or if you’ve got to do the hiring, budgets got to get done. Pick and choose what the real important things are and what you have to say. I could do that right now and it might take five minutes but if I push it off a week, that’s not hurting anybody and that can wait. The problem is it’s not just one five-minute thing. You get ten, fifteen in a day and before you know it you’ve lost three hours. You need focus and time to work on some of the bigger projects. At least for me, I need to get focused a little bit, position my mind about what I’m going to do on a certain project that I’m trying to get done for the longer term.

That was something when I came into Drips, they’re all these systems you want to roll out, put in some new processes, and help for scale. That was great at first and then I started to get more and more integrated day-to-day coming on and people going me for things, which is great. I started getting hit with all these day-to-day side processes or taking me away and delaying me from my original goals of those projects.

That recognition is what I’ve come up with is that from what I’ve seen in the past it’s like I need to sit down and say, “I need to make a clear list.” For me, it’s making a clear list of what my goals are for the projects. When I want to finish them by and realistic, that’s something else I’ve been, I won’t say a struggle with, I would always shoot for the moon to a degree, “I’ll deploy sales in six weeks.” If I had six straight weeks by myself, no problem but that’s not the case, it’s having an honest conversation with myself on what can be done. There a lot of other people that are involved in that process so I have to include them as well. That’s the biggest piece of the organization is recognizing where I’m being too optimistic, where I’m letting things that could be less in priority get in the away. It sounds very simplistic when I talk about it right now, but when I’m in the weeds and running, it’s something that I don’t always catch and see, but have recognized it earlier than I have in other experiences from my past experience.

I want to come back to all that stuff around focus and how you’re picking those projects but tell us a little bit about Drips. Give us a bit of a background on what the company does, how it operates and then we’ll dive in from there.

Drips is a conversational text messaging platform. The idea behind it is obviously text messaging. It is somewhat of a new industry in general in the last few years here for marketing purposes. This space, in particular, is wide open and it’s something we’re defining. The conversational piece of it, what we mean by that is a more humanized experience to the texting. I’m sure you’ve gotten the text of, “20% off at this company online,” or whatever or, “I saw you want a mortgage. Do you want to buy from us?” Something like that. Whereas, we will take those leads and make a much more humanized conversation. “Cameron, I saw your interest in a mortgage. When can we talk about it?” It sounds much more like a human, you feel much more obligated to reply to it.

It’s also if you say, “I’m at work,” or, “I’m in the middle of a podcast.” We can then reply to that and say, “Okay great, how’s later tonight? What about tomorrow morning?” Whereas a bot or some of the text messaging now doesn’t how to handle that. It errors out more or less because it can’t handle those responses. We’re trying to make a much more interactive experience with people which leads to better conversion rates for the customers. The idea is that our clients pass these leads, we text them, we work this what we call campaign and we try and get them to a phone call so that at some point we agree that, “Cameron you agree to call in about the mortgage that you wanted to apply for.”

Are you using humans to do this versus AI?

No, it is AI for the most part. There’s a small percentage that spills over to a human reading it, an actual human that we have. If the AI doesn’t know what to do, it spills over and the human will answer. Over 90% of it is AI. That’s where Drips being the first in the space is so far ahead. The truth is we’ve had 200 million conversations and that’s just not text. It has been over 500 million texts. It’s actual conversing with someone back and forth. You can imagine the intelligence that we and more importantly the AI system gets out of that.

It learns the different languages people use, what emojis mean, different ways you can say and ask things. It knows how to look for different tones in the text. If someone’s angry, happy or excited, we’re ready to go. We can tailor the campaign’s likewise to give responses that will help increase the conversion and the odds of getting a callback.

How do you guys charge? How does your model work?

For the most part, it’s priced per lead. You dump us a number of leads. We text them out and then anyone’s we convert over. It’s a price per lead model, then depending on size and scale, that would be the price.

I want to talk to you offline and see if there’s some work that you can do with us on the COO Alliance. Also, on a book that I’ve got Meetings Suck that people are buying hundreds of copies that are time.

I cannot wait to read that book. That’s the other problem I have is the number of meetings and time wasted. The CEO, AC, and I were talking about it. They’re important to a degree but how do you get more efficient at them?

They’re important. If you think that the average employee spends one to two hours a day either on phone calls, on video calls or in meetings and we’ve never trained them on how to show up and participate and attend them let alone how to run them. If you think about our entire labor force, they’re spending 12% to 25% of their day doing something we’ve invested nothing on. That was my whole purpose for writing the book Meeting Suck for $15. If you don’t want to spend $15 on the person, you shouldn’t have them as an employee in the first place. There might be some opportunities you guys can do for some marketing with me on that. When did you get involved with Drips? What size was the company when you got involved?

It was probably April when about $10 million revenue had come in through a business partner of mine. They’ve grown fast, double triple over the years. It’s at a tipping point where they need to get some scale. What attracted me is there are great people here. The problem is, everyone was in everything to a degree. As I’m sure, you know startup culture. You wear many hats, whatever it takes to get the job done and everyone here was on board with that. It was great, but that’s not scalable.

You need some processes. There were no real systems here. They were all about mining day. They started getting a Power BI and they understand the value in data. The data was living in three or four different systems. I have a system map I can show you in terms of you had three or four disparate systems as opposed to a network link of different systems to get that data. You know what customers are you converting, what ones are losing, where we were spending our dollars, where should we be spending our dollars. What do we think versus what we know and versus what we can prove making data-driven decisions? That’s where I came in, that’s something that I’ve done a lot using that tech background that I’ve had to implement them. Combined with the business experiences I’ve had in these past roles to bring in and prepare the company for scale.

How many employees are in the company?

We’re probably about 50 or so. When I was here in April, we’re down about 30. We wrapped up in a few months here.

What’s the leadership team look like there? How many people on the leadership team who would be reporting into who?

Our CEO, AC. Our Co-Founder and CTO is Anthony Greco. Our CSO who’s also part owner there is Tom Martindale. Tom runs the sales and corporate development side of things. Greco runs all of our development. I oversee operations and client success, along with marketing and finance. AC helps out the dotted line in the marketing team. He’s very much with the creative side, he and I work well together.

SIC 68 | Drips COO, Justin Miller

Drips COO, Justin Miller: As a COO, you have to recognize areas where you’re being too optimistic, where you let less urgent things take your priorities.


What I love about everyone here is their openness to change and to feedback. It’s something, especially when you’ve been successful you tend to want to do what you know and what keeps working. Not that there’s a lot that needs to change here. They’re constantly iterating and willing to try new things. Whether it be something I suggest, someone else suggests. It’s been a refreshing feeling to work with the team. I have worked a lot of different leadership teams, but this one seems to work well together. There are always the arguments but the openness to change and willingness to listen, it’s refreshing.

Tell us how you spent your first 90 days. You’re just even finishing that period. What was it like going into this new company? What do you think you did well? What was your strategy going into this firm to get up to speed? How did you learn? How did you get to meet everybody? How did you integrate yourself? What did you pull back on? Give us that whole tour.

For me, I want to go in and listen first and foremost. I’m fortunate I said to PE I have a lot of experience especially not taking over a company but coming into a company that might need some changes, it’s what we’re talking about here. I never want to go to the playbook. I obviously have ideas and things I’ve known in the past that work. One of the biggest mistakes that I see is someone has been successful with something before. They immediately try and push that into a company that they’re going into for a similar situation.

Not to say it may not work, but I want to first hear from everybody, what’s going on? What are their thoughts on things? What’s broken? What’s working well? Where can we do better? Get to know people their skillsets and such. That was my first 30 days or a couple of weeks was meeting and talking to anyone and everybody I could. Having them show me systems, show me different processes that we have or don’t have. Talking about their frustrations, talking about things they think are doing well.

Talking about them personally, what do they see? Where do they see themselves going? What skill sets they have? Where they enjoy and not enjoy it. It’s listening mode, taking any notes that I can. Start to build out a process roadmap, one for the system themselves and then for what kind of processes you want to put in place. What ideas we want to do. What teams bumble up the most? Present that to leadership so that’s the first few weeks and 30 days there. All that listening, talking to leadership.

If there are any immediate things we got to get done that is critical, It’s either killing the business or it’s a red flag or something that came up we’ll obviously address those first and foremost. It’s coming up with the 30, 60, 90 even 180-day plan from that point of how we’re going to implement that? What’s it going to look like? Are we all in alignment with it? That’s the biggest thing. If I go off and start, they say, “We brought in Justin. He’s here to do all these things. He’s got this great experience.” I go off down a path and they’re not behind it. Disorganization or none you need the top is the biggest killer in any business or any process or any you’re trying to do so.

Getting that alignment from leadership was a big piece of it. They were very open to it all. It got some great feedback from them, great ideas, obviously but for the most part it was, “Let’s try and run with this,” and they’re going to implement it and that’s where it alluded to earlier. The biggest thing I didn’t factor in which I learned from prior experiences didn’t quite bring into my mindset early enough was the optimism or wanting to get it done too quickly. Rollout systems too quickly, roll processes too quickly. They haven’t taken extremely long but definitely longer than I would have liked and communicated. The biggest thing that is owning that like, “This is what happened, got too excited.”

Here’s the new groundwork of plans and fortunately people are understanding of that and keep doing it. I’m sure they get sick of it. For the most part, you get a, “My bad.” We have been rolling out systems. We’re already starting to get more into data-driven decisions. Before it was all I think this, I think that and now it’s people coming to meetings with, “I ran this analysis I’ve written this data look at what we can do.” which is great. It’s fewer fire drills, with everyone wearing many hats and jumping all around. You can get a lot of fire drills and something goes wrong or it’s when you need something done and that still happens. We’re still rolling out some of those processes, for sure. That’s been a big win to try and get some of those in place.

The other big one that’s been a big team miscommunication and transparency. One of the resounding themes I got from this was that leadership was not communicating. It wasn’t they were hiding anything. It was more, they’re busy working too. All the leaders here, both the top line leadership and second leadership are very much in the weeds, they’re grinders. They are in there working and when your head down and you know what’s going on, I’m guilty of it. Sometimes you forget that, “I got to inform everybody else because we’re on the same team. If I don’t, we’re not all going in the same direction,” then we’re pulling at each other and can be going off there. That’s been something that we’ve been focused on trying to open up.

How do you get people to start moving towards the data-driven decisions?

It’s showing the value of it. First and foremost, it’s making the data as easily available as possible. Connecting systems, I tend to use a sales force model because everything easily connects into that. Best-of-breed systems but tied back to Salesforce and if need be, connect into a system like Power BI or something. The value is showing them. Take pricing, for example. You ask our price, if pricing is something that we were re-evaluating. We had a lot of pricing models, a lot of different ways of doing it. Our CSO, Tom came up with a price per lead to simplify it for a lot of reasons. It’s easier for us, easier for our clients.

It made total sense. The question is how do you then determine what the price per lead is? We’ve gone from three or four different models and ideas now are priced for lead. How do we do that? People have different ideas on what the price per leads should be, “I think it should be this, I think to be this,” then the idea behind it is coming in and saying, “We put all of our historical data into Power BI, we have verticals and categorization of customers Industries all that or we can break it down by here’s this industry and this vertical in terms of type of company that’s here. Here’s their average price per lead,” versus, “Look at this one. This is their vertical, their volume and here’s their price per lead.”

What it did showed them that A, it might not be a blanket answer and B, while they had a good gut check on certain things, there were some others that, we either would have a big mess in a good or a bad way. We were priced for lead and said, “We’re a bit way under.” We didn’t realize that they were a smaller volume but a much higher price per lead or somebody else is a much higher volume and a lower price per lead. That’s a nice part of the data.

Not saying it’s always black and white. You can certainly make data say whatever you want to some degree. Try and make it simple and everyone can understand pricings and they understand that we were all thinking one way or looking at what the data and history say. Not to say that data is a paramount answer, doesn’t mean we can’t still deviate from that. At least we’re going from a baseline of true or something in reality versus people’s guts, which not to ever ignore your gut, it’s a valuable tool in any business. It’s nice to have some backing behind it.

When you came into Drips, did you notice any people issues? Did you have to make any of the tough decisions around people?

Yeah. That was something else, that came up as how do we evaluate people? Something that was missed here and even in one of the biggest things from the employees was, “We don’t get feedback as much as we like or ever.” There was no review system. They’ve tried to do goal settings and OKRs and it became a dreaded thing. It wasn’t done right. Part of that was focused again people didn’t that have the time on it. There wasn’t a uniform committed effort to a degree and it became negative.

On the people side of it, that was one of my questions is, “What are some of the employee views? What are we seeing in terms of people’s goals versus what they’ve hit and not hit? What are their skill sets versus what their job descriptions to a degree or what we’re trying to get them to do? Not a lot of that was in place. Same dancer startup culture, that’s not surprising. First and foremost, we got to figure out a way to set some goals here. Set up a process to give the employees feedback. Make it so that they can improve, but also we can see do we know if someone’s doing well or not? With lack of data, if you’re in client success, we can’t say, “You’ve done a great job with 100% retention of your revenue and you grow another 10% here.” They had that somewhat, it was probably more impressive than I have seen for some companies.

It was nothing formalized and it was not a regular cadence. The ability to evaluate the employees and any problems that we might have was not as easy or as normal if you will. They might expect we would do it at a company. I was putting that in place. There have been a few that through discussions and focus it was either trying to get someone to refocus on something that they may have missed or realize unfortunately that it might not be a fit. Going forward that was one of our biggest things that have a big working session for the whole team. At two weeks around goal setting, making a priority showing that leadership is 100% on board with this.

We’re going to take the time to do this and be able to give that feedback to employees, set those goals and make this something that is important both for them. We also want to give them an appropriate time for professional development. You never want it to be a shock. If you’re at the point where someone has a problem and it’s a shock to everyone, to me the leadership didn’t do their job. They didn’t let them know, they didn’t train them, they didn’t talk to them. That was something that was kind of a mist that was looking to put in place.

You mentioned about communication and transparency. Give us some specific things that you do or systems that you use to have better communication and better transparency with the team.

There a couple of basic things, they used to have all hands. It was once a quarter maybe. The feedback I got, it gets missed a lot or it gets rescheduled because of the people’s business travel. The first thing was I all hands once a month, we’re doing it no matter what. We’ve had that. We’re very open and transparent. That’s why our primary source to get bigger announcements out. We’re very transparent in that meeting about what’s going on, whether it be employee changes, new product strategy, fundraising. What Kevin, our awesome executive chef is making in the kitchen that week. Everything and everything comes out in that meeting. Hopefully, new systems that are rolling out, issues we’ve encountered.

The second thing we did was put in an employee engagement tool. I’ve used a bunch of these over the years. This one is somewhat new, it’s called Engagedly. I like it so far. Like anything, there are things you wish it did more of. It’s got some great features. It takes regular employee surveys. Once a week we send out a survey. It could be how do you like all hands? What do you think of our benefits package? How’s the work environment at Drips? Anything and everything. Katie Angle, our head of HR here. We meet about once a week. We review it. The information you get out of there because we would let people submit anonymously. We encourage them to put their names. We can follow up but to let us know and honestly the information you get compared to what you think you might know, it’s so invaluable.

It’s something I’ve done before but never this regular cadence. I found it a great tool. For the half-hour a day we spend reviewing it and whatever corrections we get out of that that we take, it’s invaluable. We also share the results with the team at the all-hands meeting. Every last one when we show them what was there, the good and the bad. “You all seem to like what we did here well?” You think we missed the mark here. Also, it’s a chance for education.

We did one on benefits and one of the complaints was that we didn’t let them know early enough about the change. We are changing our benefits which health care costs changing. That wasn’t a function of us not letting them know since we only get the renewal three weeks before the time is there. Health care costs always go up. That’s the nature of healthcare. We let them know as soon as we did but obviously two to three weeks is not a lot of planning for the average person to do some rebudgeting. One of the things that could take away from me was, we may not know the amount that we’re going to be able to change but we could have said to you, “Our healthcare renewal is coming up. It’s almost guaranteed whether we change it or not, your costs are going to go up. Our costs are going to go up. That’s the nature of healthcare.” I would prepare for an X percent change in your check.

In that way they at least have a heads-up coming in. It’s a small thing, but it’s one of those things that help employee satisfaction. It helps them plan their lives. One less thing they hope they have to worry about. It’s some things like that and company culture has come up in there. I liked it. Going back to the software, smaller things it has is it has goal-setting so employees can put both company goals. We put our company goals in our values in there. They can put it in for the company, for the department and for the individual employee. We will do bi-weekly meetings with the employees. We do a bi-annual formal review twice a year.

We require bi-weekly meetings and in Engagedly, you can put little notes in there. It could be a five-minute meeting. As you can imagine, to do a review every six months, it’s hard to remember. What did that person do well? What didn’t they do? That’s the point of the bi-weekly meeting, get a quick update. If you need to put some notes in there, “Joe crushed that project that he assigned them on. Remember to do this at the interview,” or, “Justin, he’s doing a great job maybe we can get some professional development on this topic here.” It logs that, which is great. It does all waiting and everything if you want to do the scoring.

There are a couple of other tools. It keeps points if you do surveys. We also have Drips University that’s on there. It has an LMS system in there. It’s pretty robust. We started out something I put in place here. When I came in trying to learn the products, learning the vernacular here, learning our sales process. There was no formalized way to do that, a lot of people could I talked to. We started putting in these Drips universities with five and six-minute videos with two or three quiz questions at the end to make sure you’re paying attention.

The idea being, it doesn’t matter who you are. You could be in dev and sales and operations, marketing. You need to know about the product and likewise you might have good ideas about the product. About how we sell the product, about how we market the product. We started doing those once a week, you get assigned a course. Everyone in the company, doesn’t matter who you are, takes the course. It’s meant to be short, not take a lot of time and just give you information and likewise we want feedback on it. If you didn’t like how the course was presented, if we could have given you more info. If you have ideas on something that was presented that can contribute to the growth of the business, let’s hear about it.

All these things, also the point system you get assigned and you can trade those in for Drips swag or gift cards. There are a bunch of tools and I’m sure, different tools have these. With this one, for the value and a dollar spent, it’s been great. It has a homepage board. We use Slack, which I have my own personal feelings on Slack and the notifications I get. Stuff gets lost in Slack. I’m sure you can imagine and so it’s got a nice board that we can post things like office renovation, company picnic, new expense policy. Things you want to hang out for a little while. If you think about it as an old water cooler board, I imagine back in the day. It’s kind of one of those things. It has nice engagement tools that so far have gone a long way and constantly trying to tweak and get employee feedback on how we can do better.

Do you use a tool like that for customers to learn from your customers as well?

It’s something we haven’t done. We have account managers and something we’re putting in now is more client success manager. Their job will be to more do the QB hours and everything. We are rolling out a new case system through Salesforce, supporting ticket tool. With that will come a customer portal so would probably look to integrate something like that. They’re talking about a way to collect feedback, maybe NPS scores.

Take a look at one called Client Heartbeat. A bunch of our members, as we run an event called the COO Alliance, which is the only network of its kind in the world for Second in Command and the bunch of the COO Alliance members use Client Heartbeat, and quite like it.

Thank you. I’ll definitely check it out.

SIC 68 | Drips COO, Justin Miller

Drips COO, Justin Miller: Help your employees know if they are improving by setting up a process for giving feedback.


It might be worth looking at. I love what you’re doing though on the employee NPS side. Do you know what your employee Net Promoter Score is?

We haven’t put out a formal one. We’ve got these things rolling and probably a baseline but we’ve not put out a full NPS effort yet, just trying to get some of these in place.

Do the baseline.

I do need to do the baseline though.

I have all the CEOs and COOs they’re like a coach in all of our clients in the COO Alliance. We try to get everyone to do it twice a year. I’m doing mine and pick two points six months apart and roll the survey out. It’s worth doing it to get that baseline. What I do is I ask one question, on a scale of one to ten, how enthusiastically would you recommend this is a place to work? On the thank you page I say, “What’s one thing we could do that would have you give us a higher rating next time?”

Simple information you need.

It’s like the list of Santa Claus, if they say this is all the stuff they want, if we give them that then it’s easier than us trying to figure it out.

That’s a great point.

What LMS are you guys using for your internal learning? You said you had an LMS set up.

Engagedly includes that. It’s not the most robust of them but it does videos. It does quizzes, tracking, and stats. You get a lot from that tool for the money. If you want something deeper, that’s another story but it’s pretty good.

Is there any other technology tools that you guys use?

We committed to rolling out Salesforce. That’s been rolled out and we’re in the process of solidifying it. Salesforce is a god to a degree if not in there, it didn’t happen. That’s mostly not to ground people in data management. That’s how we get insights and we’re able to figure out where we are spending our time and how our trials are converting. Previously, we were in three different systems that weren’t talking together. Everyone will be in both sales, client success and we have our operations team which helps to build our campaigns and works with the customers and that such. That will all be logged in the Salesforce likewise on the marketing side, we’ve rolled out the part that’s coming off the line. Social Studio trying to pick me up to our social media. On the depth side tools like Azure VSTS for DevOps there.

You mentioned something on Slack and then you let it get away a little bit. I want to dive in around that and let’s throw them under the bus. What’re your feelings around Slack?

It’s something I struggle with it. Communication is key, that’s a critical piece. You want people to communicate. You want to make sure everyone is passing the information they need. It’s collective intelligence. That’s what I’m sure the COO knows what it’s all about mind sharing. Slack is a great enabler of that. There’s also the other side of is it too much of a distractor? Every little thought that pops into your head, you’re Slacking. Are you sending GIFs and memes all day long? Don’t get me wrong. No one ever accused me of being overly professional. I have a good time as much as anybody. To a degree, every ten seconds my Slack thing is popping up. It’s partly on me to either tune that down or mute the issues or whatnot. Does it break up the focus of work, is my question. Likewise, what gets missed in there?

We have a lot of customer channels and things like that. If a customer problem is coming up or someone in sales is trying to figure out, “What’s the best strategy here?” You miss stuff. Someone replies and it gets it pushed up in there and you don’t see it. It’s not a Slack problem per se. It’s that they’re always in my face about it. How do you balance that? We’ve got to be able to share. We’ve got to be able to keep what is important in our face and what isn’t that we can let go down in the message history there. I was not pertaining to Slack necessarily. It’s that dilemma which I’m sure is not a new one.

It’s not a new one and we hear a lot of commentary run that in the COO Alliance at our last event we covered a lot around technology tools. One of the discussion items was how do we get people to do their work instead of staying in Slack all day? There is a lot of time being wasted. It’s a great communication tool, it is for sure. It’s also training people on how to use the tool effectively and efficiently. Where we often don’t give them that training, we assume they know how to use it.

Going to go back to what you said about meetings, it’s things we assume people know how to do like communicate. They do but they might not know the most effective way. Like another effective way to come to a meeting and prepare. It’s a great point. We got to stay on the train.

Earlier on you talked about knowing what to focus on and picking the core things to focus on. Do you have a system that helps you do that? Have you taught your team how to prioritize the core projects or core initiatives to focus on?

It’s something that’s constantly evolving. I would not say I have come close to perfecting or even in a great system in that nature. The biggest thing for me, especially at the operations level, COO is overseeing a lot of different departments and areas. I need to see what’s going on. I need to know what everyone’s working on, not because I want to be micromanaging them. It helps me make decisions likewise, even if you’re leading a department you want to know what other departments working on. There’s a lot of interconnectivity there.

One of the biggest things is a project management tool you’ve seen work a lot in the past. Like a tool like Monday or something. That’s something we are putting a focus on is teamwork. Getting everyone to put all of their projects and tasks are in there. Likewise, we even want to track some time in there again. Not that we’re worried people aren’t working. It’s that data and insights into are we spending too much time on stuff or people in meetings too long? People try to do a task too much on their own when they could have asked for help and got it done in the quarter the time. That would have been a valuable use of let’s say they didn’t want to ask me because I thought my time was too busy. If I can get you down to a quarter less time, that’s worth my investment.

That’s the first piece and then it’s to a degree sticking to that saying, “Ideally we get this project done in the next two weeks.” We got a factor in that there’s going to be some things that are going to come from out of nowhere that we got to deal with. A problem that comes up. Something we got to solve with. We got a factor in an extra four or five days here. For me, it’s sticking to those deadlines in those projects and when the ones that come up and this why I haven’t found a good way to articulate this one.

Knowing which things as they come up that are the whack-a-mole, which one of the moles can stay up for a while? I’m not going to hurt you one or slow anyone down versus which one’s the ones I got a hammer down right now and I can use that allocated over budget time if you will hit them. I need a better way to express that and to help train people on that. For me, I rely on experience about, “I know, that’s okay to sit,” or, “That needs to get hit.” I haven’t found a great way to say, “Here’s a good formula for that.”

It’s hard because there are so many competing priorities on people’s time and in business areas time. The reason, I’ve tried to figure out why IT and marketing always seem to be behind on their projects. The other business area always seems to be able to stay on track more. It’s because most business areas forget to tell IT or forget to tell marketing that they’re going to be needed in certain projects. IT has a list of priorities. They plan out their quarter. The CEO comes running in and goes, “Can you integrate this into the whatever?” or, “Can you put this up with marketing?” You don’t go to finance that often with, “Can you do?” You don’t go to customer services.

We don’t hit these other business areas with all these random ideas. I’m trying to get IT and marketing to only book their calendars out to 60% of their day and 60% of their week. Leave themselves to have all that buffer time available. If you have 40 hours of project work to get something to launch, it really is going to take you 60 hours to get there because of all the other crap we’re going to throw on your plate. That seemed to become helpful. Have you done anything like that at all?

We haven’t yet. This problem we’re discussing is something that, for myself, I’ve realized probably that I need to get better at it. It’s something, talking about with our CEO that we’ve realized collectively, we need to do a better job of helping everyone else with it. Maybe it is something like you’re talking about. Our people need to book only to a certain percentage of the time. You got to prepare for that buffer zone whether it be you weren’t told or it’s a firestorm something that your customer has to have a project on or something. We’re willing to do that. That’s something we are in the mix of and have meetings on. I love the suggestion quite frankly.

It’s been working. We tried it a couple of years ago, and it seems to be working on a few clients. Tell me about what you’ve learned or what your insights were around PE. PE seems to be that mystical world. We hear a lot about venture capital firms and how to market to them and talk to them and work with them and deal with them. We don’t hear much about the PE side. Can you give us some insights there?

Yeah, it’s funny you say that. Prior to business school, which is what was made that transition from the IT firm that I own to PE. PE was this mystical thing. I don’t know what it was. Venture Capital sounded cool because I like entrepreneurship. I like working wearing many hats. I like working in different companies. Venture capital sounds like a great way to go, knowing nothing about how to get into that, in a business sense. My career advisor at school said, “What about private equity?” They’re little more established businesses. You could probably utilize your skillset without having any traditional investment banking background. I had this robust technology and operations background. They say, “You can probably utilize that into the right PE firm.”

The biggest thing with PE is it’s what you care about. It’s almost like selling to a client or a customer. What is their problem with their pain points? For PE, different funds of different things, they want to track. Some are there to invest in a specified portfolio. We want X number of tech companies, X number of retail, X number of services companies, whereas others want turnaround situations. Others want ones where they don’t have to put any operational effort into companies that are doing well.

What surprised me the most and I left the mystical thing. I always thought there would be this great process behind it. Great workflow, “Here’s how you diligence a company. Here’s the way it goes.” There’s diligence done, there’s a lot of discussions done. The decision could come down to people arguing over not their opinions but bringing the right facts here and no one’s making decisions on a whim. It was interesting because how much is it, to say it’s the Wild West would be a terrible classification of it, but lack of formality. I don’t want to sound too unfair to it. There is plenty of diligence being done and checkboxes being made. A lot of money’s being invested here. Anything goes. It’s also a good thing in a way too.

I started PE as an intern, out of grad school and they even listen to my opinion. When they’re making Investments it was like, “What do you think Justin?” All you know about me is I’m an intern. I don’t say that they ever took my advice. At least they listened. That is what surprised me the most. The number of inputs and talk they’d taken. The word we use all the time was collective intelligence. Getting me smarter on this industry, getting me smarter on this company, I want to know everything I possibly can. We can look at projections and financial statements and all that. What are the external factors? Where can we go with it? What’s the growth plan? That’s was most interesting to me, the amount of work that went into that collective intelligence build.

How about if we were selling to a PE firm, what are the one or two things we should do to get the maximum valuation to sell into a PE firm?

It’s a little bit of depends on what the PE firm is looking for. All PE firms are looking to make money, but there’s nothing special. Some, it’s more than what industry they’re looking at. Some will be recurring revenue. I want to see what you have for recurring revenue. Some want to be making sure you don’t have too high customer concentration. Others won’t care about your customer concentration. Someone knows services, some like services. Do they make you stickier? I’m probably referring a lot more to the software. My background mostly isn’t PE.

That’s the one danger we see in PE. We’ll talk to companies or we’ll talk to investment bankers who talk to the company they’re like, “They took the company in this direction over the last year-and-a-half to prepare themselves to sell the PE.” That’s probably the biggest mistake that companies can make. They try and fit what they need to do or what they’re doing to sell to a private equity firm. That gets them off course, it might take them away from their core competency. They do something they’re uncomfortable with. If you do what you’re good at what got you to where you are, there will be a PE firm that wants you. You won’t be applicable to everybody and that’s okay. It’s like dating.

SIC 68 | Drips COO, Justin Miller

Drips COO, Justin Miller: A COO needs to see what’s going on, what everyone’s working on, not to micromanage but to make better decisions.


Keep building the best company you can.

Yeah, and then you will definitely find the one that is right for you and will want you or maybe it’s a few companies. That’s probably the best advice I can give. Don’t try and fit what you think PE even wants. If you need to make some improvements do it. Don’t try and fit something else.

Final question, if you could give some advice to the 21-year-old Justin Miller, that 21-year-old getting started in his career out of college. What advice would you give yourself?

The two would be don’t be afraid of being uncomfortable. I tend to shy more towards things I knew and not to say that I’m looking to go bungee jump off a cliff but it’s okay to be in uncomfortable situations that lead to success. The second would be networking. I always joke I’m the one that doesn’t like to talk to people. I very much enjoy the value of a network and even like you talk about the COO Alliance, being able to have people you can bounce ideas off, problems off, that is so invaluable. Both in your career and your job, being able to succeed networking is key. Relationship building is what I mean or likewise if you’re looking to move around. That was something I always shied away from, especially in the tech space. I relied on, “I know this tac, let me stay in here.” Be a little more open to what’s uncomfortable, which for me was networking and relationship building. It’s such a key thing in any business, any industry. I can’t think of something where it’s not paramount to have and do.

Justin Miller, the Chief Operating Officer of Drips. Thanks very much for sharing with us on the show.

Great, thanks for having me.

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About Justin Miller

SIC 68 | Drips COO, Justin Miller

Justin has over 15 years of operating experience with a deep background in information technology management and infrastructure. Currently, Justin is COO of Drips, a conversational texting platform where he is responsible for growth through implementing relevant processes and systems, in addition to the oversight of the companies ongoing operations and procedures.

Prior to his current experience, Justin worked in private equity, primarily for technology-focused funds where he served a dual role in deal sourcing and diligence as well as serving various CIO/COO operational roles in portfolio companies. Before his time in PE Justin founded a technology services and consulting company that managed IT infrastructure and operations for banks, hospitals, universities, and other commercial businesses.

Justin holds a Bachelor of Science in Business Administration from Northeastern University and a Master of Business Administration from the University of California, Irvine.


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