Sr. Director Technology -Job Description

Are you passionate about helping people solve problems using technology?

Are you experienced helping scale a company’s technology to millions of users?

Can you lead and inspire a team of excellent engineers?

If this sounds like you, we’ve got your perfect job.

My name is Steven Cox, the Founder of TakeLessons. I’d like to tell you about a position we have on our team.

This role is entitled the Senior Director of Technology because you will be managing a lot of really cool projects related to software engineering, IT, and Systems Administration. Better yet, you will be working with an amazing team of motivated, smart, yet humble engineers.

At its core, this role is so much more than making sure all of the tech trains run on time. Instead, this is a role about forging a better path, creating the future, and building things you’re proud of. The Senior Director of Technology is our leader in everything tech - from roadmaps to infrastructure to coding to mobile apps to tools and platforms.

Here’s how it works:

Our company, TakeLessons, is used by millions of consumers and instructors each month to find and book education services and take online classes. We have two products: first, a matching marketplace where customers can find and book their perfect instructor - both in-person (locally) and online. Second, an online group class product called TakeLessons Live where customers can access live classes from wherever they are, on any device, and get the help they need.

From the first time a potential member lands on our site or downloads our app, we want to give them an incredible learning experience. Our Senior Director of Technology will be the key voice for how our technical services solve our customers’ needs.

Your day will consist of mission critical tasks, decisions, and direction that help shape our product experience. You may find yourself working on things like:

  • Envisioning, planning, and moving our tech forward
  • Helping scale the business through cloud solutions
  • Owning the tech roadmap
  • Overseeing software development
  • Jumping in and coding yourself, if need be
  • Working on site architecture
  • Software design
  • Directing QA, Sys Admin, and DevOps
  • Ensuring our internal IT systems are secure and scalable
  • Working with your engineers to develop them as coders and leaders
  • Participating in product and tech roadmap sessions with the Executive team

In your role, you will lead a growing team of engineers working in a full web development stack using technologies such as jQuery, AngularJS, Symfony, PHP, PostgreSQL, Linux, native mobile apps, and internal IT administrators and specialists.

You’ll also make sure that TakeLessons has a vision for our tech infrastructure and that we’re ready to scale into our next phase when the time comes.

But you’ll never be working in a silo. You’ll be working hand-in-hand with Product, Marketing, Customer Experience, and the Executive team to empathize with the users and build products that make their lives better.

You will report to the CEO, and have direct input as a member of our Executive Team.

If you believe you can nail all the above, you’re probably pretty incredible, which brings us to an important question:

Why should you work with us?

We’re TakeLessons and our mission is to inspire the world to connect, explore what’s possible, achieve results, and build a better tomorrow. To do this, we’ve created a top education site for lifelong learning.

You'll get to lead the direction of the company's technology and help solve some really exciting problems. We're seeing usage continue to ramp and we're thinking about how to modify our platform so it can scale like crazy. There's so much opportunity to make a difference here!

The people we work with are open-minded and focused on ways we can improve. If we find a cool new tool or service that will really benefit the company or the tech, let's use it! If you come up with a new idea or a better way to do something, let's talk about it! We have a fun and smart group that loves to figure out creative and efficient ways to get things done.

What’s really super cool for me (I think you’ll like it, too) is that we get to help instructors make a better living doing what they love. We all know how hard it is for teachers to make money, but with TakeLessons, they can teach their passion and get paid doing it! Check out some of the unsolicited comments we’ve gotten from our teachers (scroll down to the part “What Teachers Have to Say”) You can see some press about us here.

Why our mission matters

Let’s back up to 2007. I had done startups for 7 years, including a tech company that went public and another that sold to a public company. In addition to working on a few new ideas, I was filling my creative outlet by playing and singing in a rock band.

My drummer, Enrique, was a good friend and a talented musician. Enrique’s livelihood was playing music. He had a master’s degree in music performance, and he built his entire life around music.

He had just gotten married very recently, and he and his wife were trying to buy their first house in San Diego, one of the most expensive housing markets in America.

After a show one night, Enrique pulled me aside and said, “Hey listen Steven, you know that music is my life, but I have to quit the band and go find another job.”

I asked him why, and he replied, “I can’t make enough money playing music. I can’t afford a condo, and I just found out that my wife and I are going to have our first baby. I can’t do it anymore. I’ve decided to give up playing music. Instead, I’m going to just find an office job.”

For me, that really hit home. I felt horrible: here’s a good friend who had struggled all of his life to do something he wanted to do and couldn’t figure out how to make a living doing it.

So, I got really frustrated and decided to help him. We set out to help Enrique make more money by teaching.

That’s how the idea was started. Our idea was to build technology that helps people make a great living doing what they want to do vs. what they have to do.

Fast forward to today, we’ve taught over 3 million lessons, and each month over 2 million people use TakeLessons. The company has expanded beyond music to include languages, tutoring, hobbies, and more. We have also expanded the technology so now, instead of just finding a local instructor, you can access live classes from anywhere in the world, take an online class, and learn from your mobile device.

I’ll end with one of the happiest facts I can share with you. Enrique now has two beautiful daughters and he never took that boring desk job. He still teaches for us today.

So, our business matters to the thousands of instructors like Enrique that make a living on the platform.

It matters to the tens of thousands of people who take lessons with us each month, who learn, who grow, and who make a more fulfilling life for themselves and their family.

Our business matters to our society. In a world where education is so critical to one’s success, we have a personal goal to positively impact millions of users through a better way to learn.

And our business matters to our employees, too. We believe that providing a positive culture where our people can do enjoyable work - work that matters - with cool people, in a stable company, and be paid well, is a worthy goal to shoot for.

Here are the essential duties and responsibilities

  • The Senior Director of Technology is responsible for all software applications developed by TakeLessons, including our online lessons marketplace, SaaS provider toolset, online classroom, mobile applications, and internal CRM system, as well as any third-party service implementations
  • You will manage a team of engineers responsible for software architecture, systems analysis, software design, development, QA, architecture, analytics and reporting, system administration, and DevOps
  • You will collaborate closely with the heads of Marketing, Product, and other senior company leadership to understand and provide feedback on strategic product direction
  • You will identify, plan, and communicate infrastructure and architecture changes needed to meet our roadmap and manage technical debt
  • You will build and support a team of outstanding engineers (in-office, remote, possibly overseas) through interviewing, networking, and community involvement
  • If need be, you’re not afraid to jump in and code during an iteration if needed
  • You will serve as the senior technical resource within the company, communicating with and mentoring others
  • You drive the evolution of our Agile software development processes and toolset
  • You will manage internal IT resources responsible for building and maintaining office networking devices, employee workstations, data backups, and security
  • Manage contracted software development efforts and third-party software vendors
  • You help establish and adhere to resources and budgets
  • You lead a cross-functional team from requirements definition through product launch to delivering committed scope, on schedule and with the highest possible degree of quality
  • You manage all our data and reporting needs, and you develop systems for tracking metrics and measurements that monitor product analytics, impact, and success
  • You oversee monitoring systems and alerts set up by release engineers, DevOps, and IT specialists, responding promptly when necessary to address issues, including after-hours response to critical issues

So, what do you think? Does this suit you? If so, here are the details


  • Remote (USA only): You can be located anywhere in North or South America with excellent Internet and phone connectivity. However, we may give preference to someone living in San Diego, CA just because it’s easier to meet with the Exec team (also located in San Diego).

Type of Employment

  • Full-time only, salary

Necessary Skills and Qualifications


  • Bachelor's degree in computer science, software engineering, or related engineering field
  • 5 years of progressive engineering management experience, including proven success in leading software teams of 8+ engineers. You must have a passion for responsibility.
  • Expert-level knowledge and recent hands-on experience with full-stack web development on Linux, including jQuery, Javascript, PHP, and PostgreSQL/MySQL
  • Experience working on websites that have scaled up to 3,000,000+ active users per month using cloud-based hosting and a service-oriented architecture
  • Expert-level proficiency with OOD principles, software architecture, and data modeling
  • Ability to clearly and concisely communicate complex technical subject matter to a variety of audiences, including presentations to the executive team and board of directors
  • Demonstrated success in leading and evolving Agile software development teams and effectively collaborating with the Product and Marketing departments
  • Strong leadership, people management, and interpersonal skills combined with the ability to develop these skills in others
  • Demonstrated proficiency in developing and executing strategic and tactical plans for technology departments, including budgets
  • Experience creating and overseeing successful execution of short and long-term technical roadmaps
  • Experience with taking a site from USA only to international
  • Excellent understanding of the product development life-cycle processes and methodologies
  • Deep understanding of how to use analytics, data, business intelligence, and multivariate testing


  • Direct experience with native or web mobile application development
  • Direct experience with Tableau
  • Working knowledge of Symfony and AWS

Mental Requirements

Roll Up Your Sleeves: This isn’t a “sit in the office and plan” role. This is a role where you will be roadmapping one day, and in the trenches with the rest of the team coding the next. If you have graduated to the point you are above coding, you’re not the right candidate.

Communications: You need average adult reading comprehension, combined with grammatically correct written communication skills. You can present well at all levels. You can talk and present in layman's terms at a company meeting, or you can host a white paper talk to fellow CTO’s. You have the ability to understand and respond intelligently to business correspondence. You have wonderful interpersonal skills and can persuade, manage conflict, debate, negotiate and conduct meetings. You respond to pressure in a calm and reasonable manner.

Judgment: You make good decisions and take responsibility for them. You can initiate and perform work assignments under minimal supervision that may be broad, varied, and complex in nature. You know how to choose the correct course of action from a given set of variables, with limited data, and with limited direction.

Organization: We’re assuming you couldn’t have gotten to where you are without excellent organizational skills and time management skills that allow you to accomplish big goals. We want you to bring those skills with you.

Ownership Mentality: This is one of our core values. We are looking for someone who doesn’t just want a job. We want someone who thinks of themselves as an owner and steward of the company. This means you have the ability to make decisions based on what’s good for the long-term success of the organization and its people. You can get big results from small budgets. You have an internal disgust for company politics. And you understand what “We, not Me” means.

Logic: You have strong deductive reasoning abilities that allow you to apply general concepts to specific situations. You can translate theory into business practices. Your inductive reasoning has developed sufficiently to enable comprehension and use of statistical values as required for analysis and evaluation. You are able to apply technical information to identify problems and plan strategic resolutions.

Management: You have mastered the disciplines of a manager, including visioning, planning, evaluating, making hard choices, organizing, and building up your team. You don’t have an ego and can solicit feedback as well as give direction to others.

Physical Demands / Work Environment

The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

While performing the duties of this job, the employee is regularly required to work in an office setting where they will sit and talk or hear. The employee is occasionally required to stand; walk; use hands to finger, handle, or feel; and reach with hands and arms. The employee must occasionally lift and/or move up to 20 pounds.

Salary and Benefits

  • Competitive Pay: We are looking for the right person, and will pay up for her or him.
  • Access to full benefits: We have full health care, optional vision and dental, and a 401K
  • Stock Options: Remember when we said we were looking for people who think like owners? Well, we put our money where our mouth is. Each employee qualifies for stock options. Our goal is to make them worth a lot of money.
  • Being a part of an exciting ed tech startup: Yeah, we’re a bit older than most fledgling startups. But don’t let that fool you. We very much think of ourselves as a startup environment: fast moving, fail a lot, try things, no offices, no corporate BS, etc. But, since we’ve been around, that means we’ve found product-market fit and we’ve lowered the risk of a normal startup. So you get the best of both worlds - a fiery startup feel with the security of knowing we’re on the right track.
  • Freedom: We do have standard hours most of us work (8:00-ish to 6:00-ish), but we don’t micro-manage. At the end of the day, you will be judged by the work you produce and the health of your team, not by the number of Slack messages you send.
  • Working with great people: When you strip away all the benefits, all the tech stacks, and all the roadmaps, it’s really about the people. What you’ll find is that TakeLessons is filled with hardworking, honest, friendly, people who are here to build something great with their teammates.

Ready to apply?

Great! We can’t wait to meet you. Here’s the next steps:

All applicants must apply online at:

• No phone calls or agencies please

• Sponsorship not available

• We are an equal opportunity employer and welcome diverse backgrounds


If you’re not right for the job, but you know the perfect person, send them this job description.

If we hire them, we’ll give you a $5,000 bonus.

That’s right! Either we hire you, or we’d love to pay you some hard cash for helping us out.

This position has been filled. Would you like to see our other open positions?