👨🏼‍💻 I’m looking for my next role. Know of a good company? I’d love to chat!

I’ve taken the liberty of answering some questions you might have about my professional experience in the sections below. You can also learn more about my professional beliefs, and portfolio of projects from my time at edX and 2U.

Why would you want to hire me?

I’m a skilled leader who loves helping companies transform IT into a strategic asset. I have experience in IT at educational institutions, an advertising technology startup, a non-profit edtech startup, and a 3000+ person public company in the edtech space. My last company acquired the company I worked at previously for $800MM. Most of all, I love nurturing inclusive, customer-oriented, value-focused teams that become trusted partners for solving all kinds of problems.

I’m skilled at helping companies figure out when, how, and – most importantly – whether to deploy technology. I’ve built IT teams from the ground up, starting as the first full time hire and then transforming them into strategic assets for the business. I enjoy being a generalist who can develop a well-informed perspective and then assemble the right experts to get the job done. During my career I’ve:

  • helped teams shift adopt agile ways of thinking and supporting processes to become more customer focused and deliver value faster.
  • helped two companies spin up the IT, HCM, and CRM services they needed to succeed when leaving their incubator and selling off those assets as part of an acquisition, respectively
  • worked across multiple functional areas to improve major business processes, such as Lead to Cash and Hire to Retire.
  • developed a governance and strategic planning framework for my company’s DEI work.
  • developed suites of Information Security policies that focused on security outcomes.
  • prepared systems and Services for complex compliance regimes, working with legal and compliance experts to achieve compliance outcomes.

Who are you as a leader generally?

The most important part of my job is to create an environment where the people around me can be successful. At its core, this means a place where people feel included, appreciated, and safe. To make this happen, I am intentional and explicit about team culture. I call out what good behavior looks like and address how to approach bad behavior without creating additional harm. I want everyone on my team to feel comfortable bringing their authentic selves to work.

I spend time helping people understand how their work fits into the bigger picture, why it’s important, and how it’s helping us achieve our goals. No matter someone’s role, developing strong business acumen is crucial. I want my team to be able to think critically about the value of their work and to raise their hands when the value isn’t clear. When there are obstacles, we work together to remove them. When there are failures, we learn from them. When there is good work, we celebrate it.

Who are you as an IT leader specifically?

Just as I believe that IT doesn’t have inherent value, I also believe that successful IT teams don’t solve problems on their own. My teams learn to bring in the right experts to build better solutions. They talk with their customers early and often. The best solutions come from a value delivery process that includes users from problem identification, exploration, and definition, to solution building, testing, iterating, and delivery. My teams also recognize that systems quickly become complex, making it difficult and eventually impossible to understand everything at once. To address this, they develop and iterate on good architecture, define clear ownership, establish quality monitoring, and automate as much as possible.

I value good communication, healthy boundaries, and a sustainable approach to work. While I appreciate when people step up in emergencies, I do not reward continual individual heroics, as it isn’t healthy for team culture. As an IT leader, my job is to build an environment, culture, and structure that enable all of this to happen without my constant presence.

I also ask all members of my team to work on internal user-facing communications so that they think through how their changes will impact their customers. This is a fantastic opportunity to validate changes before they go out and to put oneself in the user’s shoes. Likewise, I expect my managers to include their teams’ input and insights in a collaborative planning process for their tactical and strategic roadmaps.

I believe that teams build better when they build a collective understanding of the outcomes they’re trying to achieve and how they’re going to achieve them.

Who are you as a manager of people?

I work to provide my teams with the opportunities, support, time, and resources they need to learn and grow. I learn about my direct reports’ strengths and growth areas through conversations with them, as well as soliciting feedback from their colleagues and customers so that I can help them on their career journeys. When there are clear development objectives, such as a promotion, we will co-develop an individual development plan for mutual accountability. As I support people in their development, I meet them where they are and work to develop competencies through coaching, support, and eventual delegation as they build confidence1. Demonstrated competency is rewarded with greater autonomy and new challenges.

I value curiosity, critical thought, proactivity, good communication, and inclusivity. These qualities are foundational to what sets my IT teams apart from others, and I work on developing them in every team member. Technical skills are easy to come by, but providing a delightful and truly excellent IT experience requires more than just good tech skills. When someone on my team brings a problem to me, I may have a perspective or a solution, but what’s more important to me is that we can get curious and think critically about the problem together. I want to nurture each person’s ability to solve similar problems themselves or, better yet, with their peers the next time.

What’s your recent professional history?

Over the last ten years I’ve focused my professional energy into transforming internal IT at two companies. I was the first full-time hire for corporate IT at my last company, edX Inc. I built teams that were responsible for IT Operations (e.g., Support, EPM, SysAdmin) and Business Systems (e.g., Salesforce), which included two managers and five indirect reports. I led the IT team during the lead-up to edX’s acquisition by 2U Inc. in a deal valued at $800MM and stayed on for the following year to successfully integrate edX’s IT capabilities into 2U’s IT apparatus.

During the year after the deal closed, I was also asked to assume responsibility for two additional teams. First, I started to manage the IT Infrastructure Team that was responsible for 2U’s employee identity and access management services, physical security, and services like Google Workspace. Later I assumed management of a Productivity Systems team that was responsible for Atlassian Server and Cloud Products, Slack, and other productivity systems.

What are you up to now?

I’ve been building a consulting business: The IT Witch. I help companies to build better IT capabilities at the intersection of people, process, data, and technology.

What kind of role are you looking for?

A Head of IT role at a growth stage, SaaS climate tech company in Boston or remote.

The statement is narrow by design.

It turns out that it’s easier for people to be expansive and think about adjacent opportunities from a narrow statement than it is for them to identify specific opportunities from a broad statement!

If you’d like to be on the lookout for me, I break this statement down on my Job Search page.

What are some business capabilities and IT capabilities you’ve built out?

I have experience building out, maintaining, upgrading, and transforming business and IT capabilities that include:

  • Human Capital Management (HCM) / Human Resources Information Systems (HRIS)
  • Customer Relationship Management (CRM) Systems (Salesforce)
  • Information Security Programs
  • SaaS Administration and Integration
  • Business Process Automation
  • Business Process Improvement
  • Endpoint Management
  • IT Support
  • Network / VoIP
  • Diversity, Equity, and Inclusivity

Footnotes

  1. I’ve found the Situational Leadership model to be a simple and powerful way to describe how my role as a manager (or leader generally) may change based on different contexts and levels of skill with members of my team.