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Director of IT and Operations


We are looking for an ambitious, talented and tech-savvy Director of IT & Operations who aspires to become our CIO within three to five years and who truly understands how great systems and smart design of business processes can propel a fast-growth professional services firm to even greater heights.


Reporting directly to our COO -- with extensive interaction with our CEO, President and other members of our senior leadership team -- you will define the "operating system" for how we: manage the business; deliver great work; provide exceptional client service; create consistently high-quality deliverables; and build a material competitive advantage relative to our less tech-savvy competitors.

This is the perfect opportunity for a 4- to 6-year information technology or management consulting professional, with both IT and business acumen, who prefers not to work in a large bureaucracy where one's impact is not highly correlated to one's talents and potential. If, rather than being a cog in a machine, you want to work in an entrepreneurial, employee-loving environment where you can truly make a difference and in a job that requires near-zero travel and is centrally located in Chicago's loop, then this is absolutely a career opportunity and career path you'll want to learn more about.


With a primary focus on systems and a secondary focus on operations, you'll inherit a broad portfolio of SaaS solutions and custom applications that drive all aspects of our professional services firm.

We've made considerable progress on using tech to our advantage and improving various areas of our business, but you will own: refining that roadmap; executing on it with in-house developers and external resources; and collaborating with our Service and Corporate team leaders, and other staff, to get buy in and ensure a smooth rollout and change management experience for any and all systems you deploy on behalf of the agency.

The systems you will own will span a wide variety of functions and departments: Sales, Marketing, Accounting/Finance, Productivity/Collaboration, HR, L&D, Client Service, Executive Dashboards, IT Infrastructure and more. Beyond operations, you'll also own creating any new tech that drives or accelerates the growth of the company. If it makes sense to build, we will give you a green light to build it.

On an ongoing basis, you'll put together plans and manage your team to execute on your vision. It's a lean-and-mean corporate crew, so the expectation is that you will be able and willing to roll up your sleeves on implementation work whenever the need arises.  Particularly in the beginning, but probably forever, this is not a job for those who are not able to carry a heavy load. There is next to no bureaucracy here, and we try to keep things moving!

Opportunities to Advance

After showing the world that your talents lived up to their billing, and demonstrating that you can help us to make progress on this very important work, you will be on track to become our CIO (or an equivalent senior leadership position within the firm). At that stage, you will also be entitled to participate in various programs we have designed to reward and retain our senior leadership team.


Those who apply for this position should first confirm that they have the following requirements:

Information Technology Background and Skills

  • A background in Strategic /Operational IT Planning
  • Recent experience actively coding in some capacity and a willingness and desire to code when necessary
  • At least one experience developing specifications for a custom software project and seeing the project through to deployment
  • A working knowledge of app integration frameworks (e.g. JSON, Rest API, etc.)
  • Background in operationalizing good frameworks for devops management and change management
  • A track record that includes maximizing ROI on SaaS solutions, including integrating them with each other and with proprietary, in-house systems
  • Working knowledge of IT security, network infrastructure system administration and IT support functions

Business Operations Background and Skills

  • A solid understanding of business operations and success drivers for a professional services firm
  • Experience defining and documenting business processes to improve operational excellence
  • Background in managing vendor agreements and relationships, including negotiations and contracts. Can define requirements and evaluation criteria, then solicit and vet potential vendors

Managerial Background and Skills

  • Experience in the development and management of IT project plans
  • Demonstrated ability to set and continually manage project expectations with team members and other stakeholders
  • Can identify, assess and work to mitigate project risks
  • Experience managing, mentoring and motivating a dev group with no fewer than three full-time team members
  • Experience managing third-party development partners to ensure timely delivery, usability and quality
  • An ability to collaborate with others and a strong desire to work in a company culture that deeply values learning, teamwork, playing for high score, entrepreneurship, creativity, diversity and inclusion
  • Exceptional problem solving and reasoning skills, as well as an entrepreneurial mindset
  • A love for process, continuous improvement and quality assurance
  • Excellent written communication and verbal communication skills
  • Strong interpersonal and relationship development skills

Other Requirements

  • Bachelor’s or Master’s degree in a technical or engineering discipline, preferably Computer Science (or some serious, real-world experience that made you smart the hard way).
  • Business coursework, experience or degree also beneficial.

A Simple and Highly Confidential Application Process

Here’s how it works. Apply online using the button below.  If we like your resume and cover letter, we’ll ask you to come in for an initial interview.

If there seems to be a fit, for you and for us, we'll give you a short case study to read through. You'll then come back for a second round of interviews, we'll talk through your approach to the case study, and we'll finalize next steps from there.

Easy enough, right? For the right person, this can be an amazing opportunity, so we encourage you to start the process as soon as you can, and we hope to meet you soon.

Apply Now