And Thus Begins My Startup Hiatus

I just started my third week at DragonSearch, a digital marketing company with an office in Kingston, New York. I’m incredibly excited about my role there, which is internal marketing. DragonSearch is a full service digital marketing agency whose CEO happens to have written a couple great books about social media. I’ll be helping grow our speaking program, which currently involves many events for our CEO and a few others, and soon will begin to grow the speaking prowess of anyone else in the company who shares that personal goal. I’ll also be helping with a variety of other core components of the company’s marketing and brand goals.

On my first day, the difference between startup life and office life were glaring. Being part of a startup is like being in the wild west. There is no play book. There is no person to come over and set up your phone for you. There is a lot of freedom to blaze your own trail to find an answer. One day you might be talking on the phone with the CEO of a major national brand, and the next you might be renaming image files so the API knows which objects they relate to. Would I regret giving up all that freedom and excitement for something more structured and rigid? I’m pleased to report I haven’t surrendered any of my freedom or passion. In fact, I’m motivated to blaze a trail even brighter than before.

I actually feel like I have just as much autonomy as I did previously. Sure we keep track of our time a little more diligently and we’re a bit less liberal with working from home, but if I need to find an answer to something, I go find it! There is no playbook for my role and I’m going to be able to do it my way. The opportunity to step up is just as critical, I just happen to have a much larger team working on a wide variety of projects that I can trust for support.

To be clear, I loved working for a startup. The passion drawn from developing one killer product and refining it (and refining it and refining it) really is something great. Luckily for me my new role is internal marketing, and because it’s a relatively new role, I’m still able to focus on growing one brand and I’m still empowered to innovate. I hope some day be part of a startup again, perhaps as a founder. For now, I’m looking forward to working with an office full of new people I can learn from and working for a company that highly values personal growth so I’ll never have to stop learning and developing new skills.

Breaking the Fourth Wall: When customers enter your support space

Before joining the tech community, I spent many years at a local bike shop. Customers would come in all the time looking for help with their equipment, and eager to learn how to get the most out of their experience. We sold much more than just cycling products, we enabled a lifestyle and supported an entire community of users that sought us out for guidance. Because they could come into the store, look us in the eye, and start the conversation face-to-face, there was an inherent confidence on the part of the customer that they were in the right place and going to find a solution. In the tech industry, we can take lessons from this experience to make our modern support just as charming and effective for the user.

When a customer comes into your space, not only have they broken that fourth wall, but they are doing so because they expect a favorable outcome. That is certainly the case for a main street shop, but is it so clear when submitting a support ticket remotely? The answer is that it needs to be, and we must make it so.

Most of us, no matter what side of the consumer-producer equation we are on, are unfortunately familiar with contacting support and never hearing anything back, or having a stock reply that doesn’t instill much confidence that the experience is going to yield a solution. This has two effects on users’ attitudes. Sometimes this diminished sense efficacy makes users reluctant to contact support in the first place. Other times users will shoot from the hip as soon as they are confronted by challenge without a completely obvious solution because, well it’s just an email after all.

When the expectations are so low, it’s easy to meet them. We should be doing much more than that, however, as this paradigm is shifting. Consumers now make purchase decisions based on the support they hope to receive. If your company can build a strong reputation for taking an interest in individual user, then you will do better selling your product and enjoy stronger customer retention. This is especially significant if you rely on a renewable subscription to keep the lights on.

When a customer breaks that fourth wall, contacting support, they are coming into your space. Just like when a customer walks through the door of a shop on main street, this is an incredible opportunity. If the user is the type who comes through the door with low expectations for their support experience, then you have someone that you can really make an impression on. If the user is the type who shoots from the hip for their support question, then you’ll get them familiar with the level of support they can expect. This will help mold their behavior when contacting support, and will smooth out the support process for them by setting expectations.

What you do with that process is yours to decide, but always keep in mind the incredible opportunity posed by a user contacting support. They have broken down the barrier between user and service. They want to learn. They want to use your product. What more could you ask for?

Customer Care Essentials: Building on success

Laying the Customer Care Groundwork  — This is the final part of a three post series explaining the essentials of starting out on the right foot with customer service. You can find the first post here and the second here.


Now that you have established your procedures, and then ensured that your entire team is capable of executing them, you’ll want to get the most out of the work you’ve done. Follow up with customers, especially if they contact support a lot. Make sure that you answered their questions, find our if your solution worked. This will do two things: help with market research and foster evangelist customers.

When you follow the solutions your customer care staff responds with, you’ll be able to understand whether or not the customer was successful after they contacted support. This will tell you a bit about your support process, but also should grant insight into the original issue itself. Why did the customer have a hard time finding that setting under their preferences? Maybe there is something unique about that user’s behavior that will help inform a future change. Perhaps everyone struggles with a certain feature, but you’ve never been able to figure out why. Getting in a customer’s shoes is essential here, and once they’ve broken the fourth wall by engaging your support staff, they’ll be much more eager to open up than a randomly selected population of customers would be.

Having a support inquiry answered effectively and getting your user on the road to success with your product will change the relationship that user has with your company forever. Ensuring that this process is both pleasant and effective will ultimately yield customer evangelists. These are customers who will go out and spread the good word for you. We all know that a bad review can be devastating, but some good word of mouth and a true believer out there working for you can pay dividends. When this happens, you have a lot to be proud of. You converted a moment of struggle for your user, into a positive experience that will retain that customer and help attract new ones. Best thing of all? It’s free.


This is going to be different for every company, but it usually involves enriching the lives of your customers in some way. Whatever goal you have, it will drive your product, and your company, forward. Good customer care is essential. There’s a lot more to say on the topic, but these are some good ideas to start out with. After all, your end user is what it’s all about.

Customer Care Essentials: Communicating with your team

Laying the Customer Care Groundwork  — This is part two of a three post series explaining the essentials of starting out on the right foot with customer service. You can find there first post here and the third here.


Time is money, right? In fact, the time of some members of your team is potentially worth quite a lot of money. It might seem silly to include an engineer in a conversation about customer care standards, but situations do arrise where you’ll be glad you did. With that in mind, though, it’s important that everyone understands the fundamental customer care goals of the company. This will help every layer of your organization package their work with the customer in mind.

When features are delivered to your sales and customer support teams (often one and the same), even if it’s just an improvement to a back-end process, your staff on the front-lines should be able to answer the question “How will the make my customer’s lives better?”. When all levels of the organization have this in the back of their minds, the information that is delivered down into the trenches of customer care will be much more valuable to your end-users.

You might even find yourself in a situation, as I recently did, where a developer or engineer will interact directly with one of your customers. Whether it’s scoping a new feature with input from a power-user, or getting feedback from an early adopter, these situations do happen - especially in small organizations. You’ll be glad that your entire team already shares your company-wide philosophy towards customer care. Fostering an environment where your customers can be part of the process can be very effective for both providing good support and building customer evangelists.

Customer Care Essentials: Setting Standards

Laying the Customer Care Groundwork  — This is part one of a three post series explaining the essentials of starting out on the right foot with customer service. You can find there second post here and the third here.


Your current customers are gold. Having your existing users psyched about your product, and company, is key. Setting standards of customer care - and then living by them - is essential. Good relationships will give you valuable market insight, maintain long-time customers, and help you acquire new users. Whether you have are in the process of bringing a product to market, or are already established, you have to consider how you will build on your user-base.


You’ll never be able to build on your success if you don’t understand how you got there, and that means setting your standard operating procedure (sounds dry, I know - I used to work in government, sorry). Now, I don’t mean that you need to have a SOP manual approved by some ad-hoc committee commissioned with that sole purpose, but simply put, if everyone is to be on the same page, that page has to be first established. That means setting standards for language - for example, making sure everyone on your team uses the same terms to describe each feature of your product.

It’s also important to make sure that everyone on your team understands how to speak to customers. This may seem obvious, but unfortunately it’s often taken for granted. Most of us in the tech industry wont ever make face-to-face contant with the vast majority of our users. Despite this, the lessons learned in my past life in retail certainly apply. When a user contacts you, they are coming into your space, your environment, and you need to make them feel comfortable. Think about your experiences with customer service, and spend some time working with your team to bring out everyone’s feelings on the topic. Listening to eachother speak about real experiences on both sides of the coin desk will help your team get in the right mindset and get on the same page in a more general sense.

The logistics of answering support inquiries is also importan to establish. What kind of response times will you expect from your team? Will you provide your support 24/7? If so, how will you determine who is on call? These are some of the questions you should be asking yourself. Having a good support infrastructure will help a great deal when all of these situations start to play out. We use Zendesk, which should come as no surprise since the widely popular services is used by more than 20,000 companies.