StratOp: Turning The Whys Into Whats

As Craig reflected in our first post, our company has matured over our first ten years. We can better articulate what makes us successful after working with hundreds of people and projects. We know what kind of work and what kind of relationships we want to sustain for the next ten years.

But, something else happened to our company during that decade too. For the first few years, we were a single-digit employee shop working in the same space in Chicago. Our entire staff focused on development. Today, you look up from your desk, and see it’s no longer that small company in a room. In fact, you don’t see anyone in your room anymore.

Our company is now home to about 25 folks that span over a dozen cities across the United States. The vast majority of us work remotely (even those who live in Chicago). Some employees are only a few years into their careers while others have been doing their craft for decades. We now have members dedicated to disciplines that weren’t part of our infancy—design, new business, marketing, and operations.

This change didn’t happen overnight. We’ve grown our people and processes steadily over time. Our slow approach is part of our DNA.

Growing slowly can be blinding—the longer you’ve been here, the harder it is to see the evolution of an organization when the changes happen so deliberately. We know the company’s changed dramatically over the years, but what’s working, not working, confused, or missing? What’s preventing us from growing the way we want to?

This past December, a few members of our team gathered in Chicago for a two-day StratOp session led by Tom Barrett, the co-founder of Navigate the Journey. StratOp is a system of strategic thinking exercises that align members across different disciplines together toward a common company vision. While there are quantifiable goals that come out of these exercises (financial and hiring forecasting, for instance), there are also qualitative goals that influence the roles of every member in our company.

In short, the result of a StratOp session is a list of WIN (“What’s important now”) initiatives—things the company can immediately do to start reaching our quantifiable goals. After our session, we developed teams focused on specific aspects of the company to dive further into these action plans. Over the past four months, we’ve been working on those plans to align the things we do with where we’d like to go.

We wanted to offer insight into where this slowly growing team discovered our biggest needs were, and the resulting things we’re already doing to ready the company for its next chapters.

One of the main themes of our WIN initiatives was clarity within our organization. As we’ve slowly grown, we haven’t always paid attention to clarifying roles, unifying our mission amongst different disciplines, or making sure our employees has a vision for their career here. Four of our six WIN initiatives specifically address this need.

Organizational structure

We have always considered ourselves a “flat” organization. We’ve never had a middle management tier or folks whose job was solely to manage people, and we’ve only recently started hiring teammates who have more junior-level experience than our historically senior-level team.

Once we reached 20 employees, however, we started to feel two pain points in our flat atmosphere—our management tasks relied heavily on only three people and employees started to express uncertainty about where they fit within the company now and where they might grow in the future.

So, our organizational structure initiative set out with three goals:

  • Ensure everyone has the right level of management
  • Create a good level of redundancy
  • Clarify what each employee is responsible for

For years, our three founding partners have acted as the managers of all other employees. They conducted quarterly reviews, discussed salaries, managed time off requests, and generally provided support to their direct reports. Until recently, one partner conducted about a dozen reviews each quarter with direct reports that weren’t as direct as they once were. 

To solve this pain point, we’ve appointed a few additional managers to distribute these tasks among more people. Managers share the same discipline as their direct reports and often work alongside them on projects, which we hope will create a deep level of understanding between an employee and their manager.

We’ve also documented the current roles here at We Are Mammoth and what is expected of each. We settled on describing roles using a simple equation:

Role = Experience Level + Discipline + Optional Auxiliaries

Experience levels—like associate, junior, senior, principal, or director—describe a person’s length of professional experience, their ability to lead projects, and the amount of supervision they may require. Disciplines—like design, engineering, and administrative support—have many sub categories. We took time to break down those sub categories and describe them in terms of common responsibilities and deliverables. Finally, auxiliary roles like a mentor or manager can apply to any employee.

The documentation we created directly translates into how we write job posts for new hires and how we communicate responsibilities and areas of potential growth for our current employees. Now that we can define these roles based on these different parameters, employees better understand their position within the organization, and we can more easily spot where redundancies are missing.

Hiring and onboarding

In general, our hiring and onboarding process works; we are able to find great people from around the country and train them to be successful team members. To ensure what we’re already doing keeps working smoothly and can be carried out by multiple people, we’ve added documentation about the various steps of interviewing and onboarding a new hire. Simultaneously, we’re focusing on the area in which we recognize we still have room to grow – diversity in our hiring.

As a start, we edited our job posts to be as clear and inclusive as possible. Our job descriptions now include common deliverables as well as limits that help frame what a job does and does not entail. We’ve paid special attention to the advice from the National Center for Women and Information Technology (NCWIT) including their Tips for Writing Better Job Ads and Checklist for Reducing Unconscious Bias in Job Descriptions/Advertisements.

We’ve removed gendered pronouns like he or she and extreme modifiers like “best of the best” or “rock star”. Phrases that included war references like “in the trenches”, “on the front lines”, or “armed with an arsenal of tools” stood out to us as colorful but ultimately not respectful of those who have actually been to war. In fact, taking a serious look at our job posts and trying to imagine how they might be perceived from a variety of perspectives helped us focus on using clear and direct language, which is ultimately better for everyone.

Employee experience

A big part of the StratOps process was coming to terms with the idea that things will change as we work towards our long term company goals—including the good things like the supportive company culture we’ve worked hard to nurture together. Instead of digging in our heels or putting up our defenses against change, we had to focus on ways to adapt.

The way it feels to work at a company has many facets, including these angles we considered:

  • Do our company policies match the needs of our team and the company’s values?
  • Do we have avenues to provide feedback, both positive and constructive, about our peers and the company?
  • Are we providing each employee with clear and fair expectations of what they should accomplish in a week?
  • Are we promoting a healthy work/life balance and supporting people before they burn out?

In an initiative so vast and potentially overwhelming, a key theme was to go back to basics. For example, when we were considering our options for providing positive feedback and constructive criticism to our peers, our first instinct was to seek out a software tool that would help us solve this “problem”. There are many peer recognition software products that range from gamified digital high-fives to complex performance evaluation tools, but none of them felt quite right for the relatively simple task we wanted to accomplish—pass on a somewhat private message between two people with the option to keep a few other people informed as well. We settled on something totally free, that we each already use every day, and that fits all of our needs—a simple email with the option to CC or BCC a manager or mentor.


One of our company values is to empower people, and in turn, be empowered. For those of us that have been at the company for several years, this is inherent in how we work with each other. To someone new, starting at a company that isn’t just a few folks in a room anymore, this wouldn’t be as evident.

The mission of our mentorship initiative is to create a support system for empowering employees organically. After deliberating on this objective, we realized that the most glaring need was to formalize a mentorship process focused on new employees. This would give more experienced employees a chance to empower others, while letting newer members acclimate to our culture faster. As the new employee continues on at WAM, the structures around mentorship can be removed, but the relationship should continue to grow.

We’ve already begun implementing this. For each new job opportunity, we assign a mentor to the new employee. The mentor, in turn, is involved in the hiring process, on-boarding the new employee at our Chicago headquarters, and leading periodically scheduled check-ins for the first two months. Mentors also help new employees define personal objectives they want to achieve for the company each quarter.

Retrospection and our future vision

This past December’s StratOp experience was as much about retrospection as it was about thinking ahead. The roadmap we carved out for the type of clients and kind of work we want to do required us to look back at how we got here in the first place. In the end, we discovered a path that feels right for the next couple of years. But, like any growing organism, what fits right now might not later. Then, it’ll be time to rinse and repeat the process.