My Interview with
the President of Successful Startup ONTRAPORT
on Growing a Happy, Healthy Company
If you’re like me, then maybe you identify as a visionary. Big ideas come naturally—processes, systems, checklists and implementation…not so much. Alas, when it comes to growing a company beyond five people and into having hundreds of team members, you can’t go without high-level operations and management.

Being so operationally-challenged, when I met Lena Requist at an event recently, I was dying to talk more.

Lena has a lengthy track record of building startups into multimillion dollar businesses. Most recently, as COO and now President of the software company ONTRAPORT, she’s helped grow the organization 5000% in three years, landing it on Forbes’ list of America’s Most Promising Companies, and having it recognized as a fabulous place to work.

If you’re challenged by how to grow your own team—know that you are not alone. Lucky for us at Divine Living, Lena was so generous to answer all of my biggest questions about scaling a company and managing a team. Read the full interview below to learn some of the secrets to her success.



Let’s start with your story. What led to your current role as President of ONTRAPORT?
I started out as a financial planner mainly for corporations, organizing corporate assets and helping them acquire funding. I did that for about 10 years before one of my clients recruited me away. He was a serial entrepreneur and he had an interesting venture that sounded exactly like what I wanted to sink my teeth into. It was a gym equipment company, and we grew it and sold it. Then I went on to a skincare company, grew and sold that, and then my last company was an international interior design firm. When I started there, they’d been in business for about 13 years, so it was my first non-startup. They had about nine employees. When I left, they had 55, and we were working on the largest construction project in the world. I’m a big fan of everything interior design and architecture, so I really loved the products and services we were offering. Then I met Landon (Founder & CEO of ONTRAPORT) and he was just so charismatic and compelling about his software venture, and I had never done anything in software before, so that’s that! I’ve been here for six years now as employee #7—we now have just over 100.

Wow! You’ve left a trail of success behind you. What were your big initial tasks as employee #7?
The first thing I did was evaluate where the organization was in terms of structure and processes—do they have ways to bring on new employees, do they have health insurance, do they have payroll? Literally it was such a startup that our CEO was writing payroll checks out of his personal checking account, so there was a lot of infrastructure to put in place just so we were an appropriate business.

Probably the biggest impact I made when I first started was in coaching a couple of our support reps to create our very first training manual. Our software is extraordinarily complicated. If we were going to bring on any more reps, we were going to need a way to bring them on quickly, make them effective and hold them to standards right away to see if we had a good fit or not.

Previously, those support reps basically spent six months sitting watching someone over their shoulder to learn how to use the software. That just wasn’t going to fly. The training manual project showed that all of our employees have the ability to take on projects and initiatives, see them through to the end and do a quality job.


Awesome—so interesting! How has your role evolved going from COO to President?
The main difference is that as of January of 2015, I really took on managing the marketing team in addition to some of the other responsibilities I have here. Now my job is really overseeing our leadership team of six people, and the marketing team to ensure that we’re moving forward on campaigns and initiatives, and that they’re effective.

So speaking of managing people and processes, I think a lot of us here at Divine Living can relate to the idea of being a visionary—wherein management is not always our strong-suit. At least for me (and most women reading), having a true COO would be like a dream come true. As a former COO, what can you tell us about that role? At what level does a company need to be at to bring on a COO of your caliber?
I get this question quite a bit actually! Everyone is like, “Where can I find someone like you?” And it really does depend on where you’re headed with your organization. With a team that’s not going to grow beyond 10, 15 people, you really just need an operations manager—someone who’s a little bit lower level—to manage the day-to-day: making sure bills get paid, setting up some processes, streamlining. Whenever I’m hiring an operations manager, I look and see if they have any project management experience, and I find out what size office they’ve run before. Those two things typically will give me a good indication of whether this person will be successful here.

There are a few levels in between, but at the other end of the spectrum is the COO—who can come in if you want to grow to an organization to over 100 people. This person would have an experience in finance, understanding how financial models work, and when and how a scalable business operates.

Every process you do in your business has a cost and a return on it. Small manipulations to these processes will impact your bottom line. For example, at ONTRAPORT, we have something we call “on-boarding,” where every time a new customer signs up, we put them through two hours of one-on-one time with one of our client success reps. It’s a pretty expensive venture. A lot of companies charge for that, but we do it for free.

Even though that process costs me a lot, I know that our customers who go through it in their first 90 days will stay with us forever, so while I’m putting a lot of money up front, I’m getting a lot back in the long run. A good COO will see these types of initiatives in your business and be able to organize them accordingly.

That makes perfect sense. You’re making your customers better, too. Tell us a little bit about ONTRAPORT and what it offers women entrepreneurs in service-based industries.
Well, we’re a business and marketing automation tool. Imagine that you have all these different things you need to do in your business. You have to follow up with the potential prospects. You have to send out invoices to your customers. You have to make sure that they’ve paid. You have to call your new customers and say, “Hello and welcome.” All of these processes are kind of manual, human-run processes.


Our software essentially automates any kind of step one, step two, step three process. You do these things in order every time, and our automation engine will do them for you. If you need a human interaction to happen, for example, if there’s someone who’s been on your website three different times, you want your salesperson to call them and see if they can help them, we can generate a task to your salesperson, and that person will then see it and call the customer.

Amazing. Why do you think this has been so game-changing for entrepreneurs? Is it filling a void for smaller businesses?
Yes—ONTRAPORT is really an enterprise tool that reimagines management for the very, very small business owner. Something that wasn’t possible even a few years ago. You would have had to pay thousands and thousands of dollars every month to get a tool like this, and so it made more sense for the small business owner to just have an employee do it.

Now for as little as $79 a month, which is nothing, you can have a tool which is essentially an employee that will work 24 hours a day, seven days a week, and never fail. I think that’s a very attractive idea for entrepreneurs.


The other successful aspect is—and I hear this all the time from our customers—is that our customer support team is just beyond, beyond helpful. They’re so friendly that it makes people feel like, even though this is a cold robot software tool, they actually have a team of people that is inspired to help them succeed and to make sure that the software is working for them.

I love that! So I work with women at all levels of their entrepreneurial journeys from just starting out to crossing multiple seven-figure businesses. And one of the biggest challenges across the board is team leadership and management. We’d love to pick your brain a bit when it comes to team building. ONTRAPORT landed on Achiever’s “Most Engaged Workplaces Award.” What do you feel has been key to earning that distinction?
There’s a way we organize ourselves here at ONTRAPORT that is significantly different from a lot of companies. Most people think work is work. You show up. You have a pile of work, like a to-do list, and you try and get through it that day in between emails and distractions. Everyone thinks that’s the way work should be.

The way we think about work at ONTRAPORT is that there are actually two different types. There’s business maintenance, which is your job description and your to-do list. This is the stuff that you just have to do everyday to stay afloat. Then there’s project work. Project work is creative, innovative, and it moves the business forward.

In a lot of organizations, the people who get to do the creative work are the people at the very top. Everybody else is forced to do business maintenance all day long, which, if you had to do business maintenance all day long, you would want to blow your brains out because it’s just very monotonous and boring and it doesn’t inspire you.


How we have organized ourselves at ONTRAPORT is everyone in our organization spends about 50% of their time on business maintenance and the rest on projects. We’re very organized about it. We have project managers and timelines, and we list out the deliverables and have people apply to be on different projects. There are cross-departmental projects, department projects, and personal projects.

What happens is people come to work in the morning so excited to work on their project, and they get through their business maintenance so much faster. They get to see the difference their projects make to our organization. It’s another reason why our company has grown so quickly —we have a team of 100 people now working on projects, driving innovation in our organization everyday.

Speaking of that team—how do you find A players and what’s the secret to keeping them happy?
They always say, is it the chicken or the egg? If you have A players, you attract A players. That’s just the way it is. I think setting up your organization to have only A players is the key first step.

When I first started at ONTRAPORT, we had a lot of good people—there were only six. As we brought on more, some of them weren’t as good as others. I started looking around with our CEO, Landon, and identifying the qualities of our really good people that we really liked. What did they have that the other people did not?

We came up with a list of qualities. and those morphed into our values as an organization. As soon as we had these values, we shared them with our current staff. We started posting them in our job descriptions. We started interviewing on these values. We started disciplining around these values. We gave out awards around these values. All of a sudden the people who wanted to come work for us were representations of these values, which were actually the qualities of the A players that were already on our staff. Then the people who didn’t fit into those values, they just left.

That’s excellent. So what are your thoughts on virtual versus in-person teams?
Back in the early days of ONTRAPORT, before I came on board, we actually had a virtual team. Everybody worked at home, and there were only five of them, so it wasn’t too hard to keep track of.

When I first started talking to Landon, it was about a year before I joined the comapny. I told him my opinion about in-person teams versus virtual teams. There are so many hidden benefits of having in-person teams that I have found over the years. Plus, I’m kind of an extrovert and I don’t like working by myself, so I was just sharing with him what I wanted for me to join the team. He said he’d try the in-person team.

What he found was that when in-person communication happened, everything changed. Things got clearer. Work got done more effectively. The quality improved. Less time was wasted with the back and forth. That’s one of the benefits.

The other kind of hidden benefit is the experience your team has while they’re at work because now they’re creating a community. They’re creating friendships. They’re creating involvement in other people’s lives. They’re helping each other with their work, and all of a sudden this community ends up taking on a life of its own, and it’s a benefit in itself.

When it comes to leading a team, what are some of the top mistakes you see people making—or that you’ve made yourself?
Micromanaging! I know that word gets thrown around a lot. I think what makes really productive, happy teams is if you give excellent, super clear direction, and then let people do their thing. I have learned this lesson so, so many times. I tell someone, “Hey, I want you to get this done.” Then they’re motivated and they go about getting it done. Then it comes back to me and it’s not exactly what I wanted, and I’m kind of bummed, and then they’re bummed because they worked really hard on it, and they were trying to make me happy, but it’s not what I wanted.

So really the problem lies with me in that scenario, because I did not set them up to be successful. It’s not their fault. They were doing the best they could. They don’t have all the information I have to be successful, so I need to give them the information. I need to tell them why this is important. I need to explain what I want to have included, things to consider, inspiration—really, really clear direction. I have to take the time to do that and then let people move forward and be creative and work autonomously and then come back. You don’t want to end up micromanaging through the process because you didn’t set it up properly to begin with.

One trap business owners can fall into with micromanaging is when they start to feel like, “I can do it better, faster,” and fail to delegate. What do you say to someone who thinks that?
Of course, you can. That’s why you make the big bucks. That’s just the way of life. Of course, you can do everything faster and better. The challenge, though, is there are other more valuable things you could be doing with your time than just that one thing that’s faster, better. So you really need to look at this delegation as an opportunity to invest in your staff members and have them get to your level, which is awesome because then they’re more motivated, they’re excited, they’re taking on new things, you trust them, and at the same time, you now have the space and availability to take on higher-level, more valuable things.

Talk to us a little bit about ONTRAPORT’s “Women in Business” community. What inspired you to create it?
When I worked as a financial planner at Smith Barney, I was one of two women in an office of 160 people. When I started my career, women just weren’t in the workplace as they are today. Now what you expect to see is half the workforce are women. At the same time, there’s this dichotomy where women can have it all and they can actually have it all. You know what I mean? All the problems, all the headaches, all the guilt, trying to be everything to everybody, trying to fit into traditionally a man’s world. I feel so grateful and appreciative that I’ve been alive and working during these past 20 years, to see the evolution of what’s available for women now in the workplace, and that they no longer have to fit into any masculine molds. They can be their total feminine, authentic selves without the guilt of traditional gender roles. There are so many amazing qualities about women business owners and entrepreneurs and leaders—I just want to give them the confidence to know that they’re in the right place doing the right thing, and to forget about the rest.


Amazing. You’re so generous in sharing your business savvy with women entrepreneurs, including those reading this! Where else can we learn more from you? Any books in the works?
I actually have a couple of courses that I teach, and I speak on this type of stuff all the time, so you can tell I love it. I’m super passionate about entrepreneurship and business building. It’s super fun for me. When it’s fun for you, it’s just easy. It just kind of flows out of you.

In terms of writing a book, it’s so funny. I think it was our Chief Media Officer, she just mentioned it to me this week. She’s like. “You know what, Lena? You’ve written so much content. Maybe we should just turn that into a book.” I said, “You know I was actually thinking of the same thing over the weekend.” I’m like, “When I go on vacation, I’ll just write my book.”

Nice. There’s your answer.
There’s my answer. It’s so very synchronistic that you just mentioned that.

See, it’s all kismet. Now you’ll have to do it!


For more from Lena, check out her latest ONTRAPORT
guide for entrepreneurs:
The Ultimate Blueprint to Email Marketing


What else are you dying to know about team building and management?
Leave us a comment with your biggest questions!


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