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Meet ONTRAPORT’s new OS, Olivia
She Manages Your Business, And Your Life

Now you can use your voice to run your business anywhere in the world.

Meet Olivia by ONTRAPORT — your new hyper-mobile business consultant. You can talk to Olivia as you would to your best friend. For example, you might say, “Olivia, let’s review my marketing dashboard,” “Olivia, let’s write an email” or “Please delete my browser history from the last 35 minutes.”

Olivia not only listens to everything you tell her, she also has your back. She navigates your all-in-one business solution ONTRAPORT from the cloud with ease to make managing your business on-the-go more convenient than ever.

Then, just like a personal assistant, she responds to your every question, command, and violent outburst. Olivia schedules sales calls, sends messages, builds marketing campaigns, questions your self-worth and more. How much more? Much more than you asked for.

10 Years of Trial and Error
This concept of “Trial and Error” is near and dear to me because, frankly, I owe my career to its practice.

Let me set the stage: I’ve worked at ONTRAPORT since I was 20 years old. The night of our first company holiday celebration I was barred from the after party because it was in a 21-and-over nightclub. So I’ve done a bit of growing myself these past six and a half years. In fact, long before I found my place as the Marketing Manager, I tried and failed my way across nearly the entire company. I spent time on the support and services teams, sales and partnerships, I was even our very first Quality Assurance rep (for about a month – failed my way out of that one real quick). So when the time came to write an article on this topic, I felt uniquely qualified.


I’d like to start by focusing on the “trial” part of the term because before you can fail you must first try. We as humans like to believe we do a lot more trying than is actually the case. I’ve witnessed this first hand in our growth as a company.

For example, we once talked about wanting to enter into the entrepreneurial education arena. Eventually the talking turned into planning, and the planning turned into, “Ah, we’ll come back around to this later because something else came up.” It wasn’t until we truly dedicated ourselves to that project that we ended up with over thirty ebooks, five expansive blueprints, and an entire website dedicated to entrepreneurial educational courses. Did we make errors? You betcha. I cringe at the thought of reading our first drafts of some of our early ebooks, but you have to start somewhere; you have to try.

Now shifting focus to the “error” part of the term: Let’s not mince words here; we’re talking about failure. Too often we associate failure with defeat — a crushing blow from which you can’t ever recover – but that’s almost never the case. Failure is only that dramatic when you’ve never stared it in the face. Make no mistake: failure in the right context is an asset, and there’s a difference between “good” and “bad” failure.

Bad failure is forgetting to put a tracking script on for six months after a complete website redesign.

Good failure is developing a test around whether we should run cost-per-click or cost-per-conversion ads. Then spending $400 to prove, beyond the shadow of a doubt, that we should focus our advertising efforts on conversions rather than clicks. Then applying that information to future advertising campaigns in order to 10x our results in less than a year.

See the difference?

Despite our marketing failures… we learned from them. We gained knowledge from them and, considering the average cost of a college education is something like $100,000, I’d say we got off easy.

In fact, I’m fairly certain the only reason I was put on the marketing team was due to the fact that I’m excellent at failing. Make no mistake; trial and error is at the very core of what marketing is. You put your message out there in front of people who you think will listen, and they don’t, and you try again. You have to be able to learn from your mistakes and pivot, quickly.

Take Instagram for instance: Instagram’s first iteration was called Burbn and was originally built to be a check-in style app. After its initial release, they realized the product wasn’t great; the market was cluttered and Foursquare was dominating that space. So they switched gears, rebranded and remarketed themselves as Instagram – a photo sharing app – and the rest is history.

This idea of trial and error to me, really, is a mindset; it’s intentional action and reaction to the results. It’s easy to post a motivational quote on Facebook, but to actually put your time and money down on something that has a chance to fail? That’s easier said than done. You have to develop theories, build campaigns and be so confident that they’ll work that you’d be willing to stake your life on it….only to end up being totally and completely wrong.


10 Years of Culture: We’ve come a long way from three dudes in a yurt
Over the past 10 years we’ve hired 192 staff members. Several have left at some point along the way, and many more stayed with us year after year. They entrusted us with their livelihood, their growth and to build this community into something more than just a job.

When you think about starting a business, you usually imagine one of three outcomes:  

  1. You see a problem in the world and just can’t sit by idly. You imagine a world where that problem doesn’t exist, and your product or service is the perfect solution.
  2. You’re tired of the 9-5 grind that is uninspiring and keeps you from the people and things you love. You imagine working for yourself, making enough to get by, and having the freedom to spend your time on what you love.
  3. You know that the only way to earn the income you deserve is to start your own business. You imagine coming up with a cool business idea that will make you millions and deliver early retirement.

It’s interesting to notice that in all of these visions, most people don’t imagine being an employer. Being “The Boss” is often a sudden and surprising experience for entrepreneurs, and we were no different.

In the beginning, we hired people we liked (and could afford). They didn’t always know what they were doing, but, hey, neither did we. There was a vibe of hustle in the air. We were all just a bunch of kids “playing” at work, hanging out on the weekends and stumbling our way through. We didn’t have stated values or processes. Heck, we didn’t even have payroll. People would just tell Landon they needed some money to make rent, and he would write them a check. In many ways, it was a lot simpler when we first started. At the same time, it was also so much harder than it is today.

Over the past ten years, we turned that rag tag group of kids into real professionals with real skills running a real business. As we methodically worked towards our mission of removing the technical burden from entrepreneurs, we discovered that ONTRAPORT was something more than a software company, and we were more that just “The Boss.” We had an incredible opportunity to create a new kind our workplace where people could engage their talents in unexpected ways, track their individual contribution, and develop new skills. Our vision began to expand to more than just the business we were building, and we started to imagine our lives as employers.

Today, our ONTRAPORT culture has taken on a life of its own, led by our nine values. On any given day, you can see our team working together, supporting one another, constantly learning and growing. They are driven by a common goal to protect what we so carefully created over the past ten years. When new staff joins our team, they discover that they have instantly gained a community of people who truly care about each other, and inside this ONTRAPORT bubble, people thrive. 

Ten Years of Tech & Infrastructure
As ONTRAPORT celebrates turning ten, it gives us opportunity to reflect on how far we’ve come and lessons we’ve learned along the way. I sat down for Q&A with Pin Chen, CTO for ONTRAPORT, to find out just that and more.

How did it all start? What’s different now?

Pin:  A lot has changed in 10 years. When we first started, Landon [Ray] and I were working on a completely separate project — not ONTRAPORT software as we know it today. The first version was actually something we built to service our own small business needs. At some point Landon realized what we had built was a great opportunity and, along with Steven Schneider, our principal architect, we set out to make it a marketable software solution. When we started, it was just the three of us sitting out in the yurt trying to make the first public version of the product.

The concerns way back then do not even resemble the concerns we have now. It started as three people in a tent and is now a team of 25+ engineers focusing on all sorts of varying projects.

Back then we were, “Let’s get this into the market. Let’s make something people might like and use.” Now, since we have a product, our priorities have completely pivoted.

Security, stability and usability are now our top concerns. Through the years we have so much more information provided by our Sales and Customer Support teams on what’s working and not working for our clients so those concerns can be dealt with quickly. Now we find ourselves dealing with these three things instead.

When you first started, what equipment did you use?

Pin: We didn’t even have laptops. We had to lug around some old Dell computer. I remember that we would have a meeting, without computers or a projector, then go back to where our computers were and start coding and trying to remember what we just talked about. We didn’t have a testing area so when we had new changes we would push that directly to the clients.

Contrast it with now. All engineers get their own laptop, and we have many layers of extraction between the programer and our servers/code which results in a much stabler system.

What happened when we had our first customer?

Pin: Landon handled all the sales, and Steven and I took care of the coding. So whenever a sale happened, and in the beginning it wasn’t the most frequent thing, Landon would say, “Hey we got a sale, BUT we need to add this feature or make this change to make it happen,” and we’d respond, “Yay, let’s get back to work to make it happen.”  So, with the first few customers and features everything was a step forward. Each new client presented their own unique challenges, and as we continued to improve the product the whole experience became more and more real.

It was very exciting, those first few customers. With each new one we had the feeling of forward traction along with a renewed challenge of, “How do we get the next one?” There was some point, I want to say two or three years in, where something big clicked. We came out with Sendpepper, and we were able to land a few really big contracts. It was an exciting day when we got 100 or 150 sales all in one afternoon. Definitely a day of celebration.

Tell me about how you learned through trial and error.

Pin: That approach really speaks volumes to the Engineering team over the years. Steven and I jumped into this project directly after college. We didn’t have experience building and developing software for the web much less as a service….or with scaling it out to thousands of clients. Everything for this project was learn-as-you-go.

Also when we first started, there weren’t quite the resources out there on the web. Nowadays there are so many solutions floating around for the challenges we once faced. You have your pick of solutions. Back then, it was a lot of banging your head against the wall until something worked.

That’s not necessarily a bad thing. With each client and challenge we faced, we became more and more battle-hardened to be able to quickly and effectively solve problems.

How has the profession of being an engineer changed in 10 years?

Pin:  I can’t speak for the industry, but now at ONTRAPORT we have fewer generalists on our Engineering team. Most engineers on our team are no longer the jack (or jill) of all trades. Back in the day Steven and I were considered full stack developers. We did everything….from changing the design, to sending out email, to making the application faster or tuning the servers. Now we actually have built teams for specific verticals: Steven and I now work exclusively on the back-end, which primarily deals with scaling and business logic; Jesse and Lorenzo, a couple of our senior front-end engineers, work on UI and what people see and interact with. We have systems admins who make sure our servers are fine in the dead of the night, and we even have a dedicated QA team making sure our new changes don’t break old stuff.

If you were to look at the Engineering team today versus even last year, two or three years ago, it has dramatically changed in the way we do our processes, the way we handle code and QA code. We feel that’s a good thing. Every quarter we make 5-10 changes to our processes from the things we’ve learned over the course of that quarter.

What else has changed in the past 10 years?   

Pin:  There are many things. I mentioned how the makeup of the Engineering team is so fundamentally different today than it was even a year ago. Along with that, the tools we use to write good code, the way we assess new hiring candidates, or troubleshoot bugs….all this has evolved.

In terms of fundamental shifts, with technology everything changes so fast, and you have to continually adapt to make sure the solutions you’ve created previously continue to service the market in the way you want it to and also the way that the consumers want to use it.

Every year you’re presented with new hurdles and challenges, but and the tough part is really understanding the flaw and trying to solve it, not just for now but enough to be viable for a few years.  

Fast forward to 2016. What is the most important thing you are now working on for customers?

Pin:  Now that we have most of the feature sets small businesses need, the most important things my team is working on is usability, stability, and security.

Usability is an obvious one. We have some of the most powerful tools for small businesses, but if you need outside help to figure out how to use the thing, then we’re missing the ball. This year we have exciting changes to address this.

Stability is next. I’d say we’re in line with the industry in terms of app up-time, but this isn’t enough. Our mantra is, “We can never go down,” because if we do, our clients suffer because of it.

Finally security. It’s not often talked about but is as important as the other two. Clients need to know that their data is protected, secure, and backed up.

In ten years, what lessons have you learned?

Pin:  Lesson 1: Writing software takes longer than you think, especially in engineering where you have new team members and a growing crew. Things always seem so easy from the mile high view. You finish the first 99% easily but spend a bazillion hours on that last 1%. So spend the time trying to think through the details.

Lesson 2: Project management is something that should not be discounted. As your team gets bigger, having someone run the processes you have in place makes a more effective team. Having the engineers manage their time does work, but it’s not the best utilization of their talents.

Lesson 3: Flexibility is very important for a team. I would say one of the strong points in our history is the ability to be able to switch between different needs…to have the freedom to expand a new feature or get input on the product design, to do what it takes to crank out an amazing feature and product. That is part of our DNA.

What’s next?

Pin:  Technology is evolving so fast that most of the things you dreamt about doing five years ago can be done. I feel like the next big shift is making things easier to use.

Usability is going to be the key to everything. Customers are less willing to put up with hard-to-use software and are looking for the easiest way to accomplish their goals.

They want to be on the go with their phone, on their tablet. They want to solve tasks and have automation triggers — all built out and easily understood.

Along with that, our user base is getting way more sophisticated. Back then, you needed a consultant to hand-hold and teach you all the things, but now… even my younger cousins can almost build a online business in no time at all.

They understand the tools, the mechanisms, how it all works. So I think the industry will have to change to accommodate that.

What else?

Pin: 10 years… it really doesn’t seem like 10 years when you have an inspirational project like this. Over this time, I haven’t had a moment to sit down and reflect on all the changes and progress we’ve made.

So during this interview I’m thinking, “Wow, that was pretty amazing to go from three people to what we have now! How cool was it to put in this system or change this team or even hire this critical person at this time?”

I’m pretty proud of the overall body of work, and I’m excited with the people here and how we share ideas and challenge each other to do quality work.



ONTRAPORT Turns Ten: What We’ve Learned from 200K+ Support Tickets
As we at ONTRAPORT celebrate turning ten, it gives me an opportunity to reflect on how far we’ve come and lessons we’ve learned.

During ONTRApalooza 2013, our annual business conference, I presented “What ONTRAPORT Has Learned from 100,000 Support Tickets.”  Three years later we’ve more than doubled that number, and the lessons learned continue.

ONTRAPORT’s mission is to reduce the burden of technology; the role of the ONTRAPORT Customer Support team is to efficiently and efficaciously get customers set-up and started and to be there along the way as their business flourishes.

But it’s no easy task building a responsive and well-loved Customer Support team in a new industry while undergoing massive growth, launching new products, and updating legacy products. Yet, we wouldn’t exchange the experiences, interactions, and clients for the world.

It All Started in a Yurt

We didn’t start as an industry-leading Customer Support team. We were a ragtag team of dedicated agents working from our homes, in garages, and in a yurt. We grew up and leased a co-sharing office space then finally found our “home” in our current campus. Yet, through the years, no matter the physical location of our headquarters, our focus hasn’t wavered.

The first support rep for ONTRAPORT was, as it is in many software startups, the CEO. Landon Ray, ONTRAPORT’s founder and CEO, and Pin Chen, co-founder and CTO, fielded calls and answered customers questions daily.  

Imagine having a direct line to ONTRAPORT’s visionary and first engineer!  But both realized that the process wasn’t scalable. We transitioned from Landon and Pin to ZenDesk, a startup specializing in help desk solutions. This freed Landon and Pin to focus on the product and market. Little did we know at the time that organizing client requests into a central repository set up ONTRAPORT to create the experience and platform that we have today.

Ten Years Later

Now, eight years after moving to a unified help desk solution, we’ve been able to make significant advancements in supporting and anticipating our customers’ questions. We see where in-app queries arise and feed that to the CEO and product team. We notice the features our successful customers are using and create training and in-app projects around how to implement those in your business. It’s our intention to make using the app is as frictionless as possible while always being a chat away.

“Lance was awesome as always. Thanks.”

-Bryan Skavnak, The Happiest Golfer

With our expanding hours, commitment to hiring in Santa Barbara, extensive new hire training and expansion to new regions, such as Asia Pacific, we’ve been here for ten years and holding steady.

Now, we’re a 20+ strong global Support department that has learned much about our clients’ hopes, dreams, and businesses. Through countless conversations and chats, we’ve honed our efforts and training around delivering answers to questions that let our customers get back to working on their business rather than in it.  

“Kelsey is awesome. She was patient, had a good grasp of the program and was able to answer all my questions. She followed up with me by sending an e-mail with links to discussion points we touched on during our call. I found her voice to be quite pleasing to the ear. My experience with ONTRAPORT since day one has been exceptional. I am so glad I didn’t sign with your well-known competitor. Don’t grow out of what makes your company exceptional. Customer service and a powerful program makes my life as a startup a little bit easier.”

-Patrick LeClaire, New Life Tax Resolution

ONTRAPORT prides itself on its customer support. We believe it is one of the key differentiators we possess in our mission to support entrepreneurs. Whether it is extra support hours to cover our global client base or extensive internal training programs, we invest in both support and client success. More than attending to customer requests, we actively sift through your questions plucking out feedback gems that help us improve both the product and our ability to assist our clients in their business and keep them focused on their passions.

We [Heart] our Customers

Much is said about analyzing customer interactions and crafting the perfect customer journey. We like to think the ONTRAPORT Customer Support team is on this journey with our clients. We’ve shared both the growing pains and the wild successes of our clients first hand. We rejoice in a successful launch and advocate with product based on your feedback. We regularly share our clients’ stories of how they use ONTRAPORT in innovative ways. Many of us have met you first hand and even more of you have spoken kind words about our team. Even if we haven’t met you, we’ve been here the whole time.

Here’s to another ten years!