Since 2010, I’ve been religiously blogging about the ToutApp journey, but about 24 months ago I had to go on a blogging hiatus except for one small post about personal growth.

Over the past two years, ToutApp has grown from seven people in size to 60+ people, delivered strong quarter over quarter growth, raised $3.3m and then $15m of venture capital from the best venture capital firm in the valley, and have built a crack team of badasses across our executive and management team.

One of the key things I had to focus through this period of stellar growth was my own ability to scale as a CEO (a solo founder at that).

I’ve had to reinvent my role several times – almost like installing a brand new operating system because the company’s needs were just so different.

As I pick up blogging again, I wanted to start by talking about the single most important thing I’ve learned as a Founder and CEO here at ToutApp, it’s what I refer to as Operational Ruthlessness.

Vision vs. Execution

Everyone knows how important it is to articulate a vision and a path to get there for a CEO.

Founder CEOs that are all about product, the customer experience, and about growing a big business by achieving a crazy vision often times don’t appreciate how important the day to day cadence and operations of the business is.

For me, I realized the power of it when we had doubled in size in headcount but still didn’t feel like we were doing “double the work.” right in the middle of 2014.

This is when I developed my ideas around embracing Operational Ruthlessness.

Being Ruthless About the Pace of the Business

Operational Ruthlessness means thinking deeply about the drumbeat of the business, thinking deeply about the recurring meetings that drives the management and cadence of the business, and ensuring that you’re setting an aggressive pace and direction for the business so that everyone knows what it means to hit the next important milestone.

I think that Founder CEOs tend to think about the basics of operational ruthlessness as they start to build out their team — I certainly did. The basics include:

  1. Setting up a cadence for the executive team to meet
  2. Conducting All Hands and making sure everyone stays in sync and connected to the vision
  3. Having the basics of a recruiting process — often times insuring the CEO is still the last person to interview serving as a stop gap for hiring managers
  4. Starting to hold off-sites so that you can talk about the strategic issues instead of being stuck in the day to day

All of those are great. And if you’re not doing them yet or feel that they’re overkill, you’ll definitely see and feel the need for them as you surpass ~25 employees. But in order to achieve true operational ruthlessness, you need kick it to the next level.

Some of the more advanced things that I’ve either already implemented or have started to include:

  1. Solidifying the culture at the company as you hit critical mass, feeding that into a formalized recruiting and employee on-boarding process
  2. Setting up an All Hands structure where it’s not just me talking about the vision, but a clear schedule and cadence of updates that gets all departments talking to the company and getting everyone in sync on things going on across the company
  3. Going beyond just a sync with your executive team to defining a concrete set of KPIs that monitor the business on a week by week basis, ensuring that not only are the executives dialed in to the objectives for the company but so are the middle layers of management
  4. Realizing that middle management can make or break companies, so establishing systems, processes and training programs to develop them, nurture them and help them grow to be successful leaders — and more importantly, ensuring that managers are truly there for their employees
  5. Constraints and financial discipline around the business. This is paramount. It’s easy to just blow a bunch of cash around that Dreamforce sponsorship, and to double down on each-and-every-event-or-roadshow that comes through the door (believe me, there will be plenty) but getting your company, your executive team, your managers, and your employees to start thinking about the cost/benefit of just spending vs. being scrappy, creative, or just plain smart about where and how you spend dollars
  6. And most importantly, starting to a) create an environment and b) defining a rhythm for the entire business. When you look into the most successful and long lasting businesses, even amidst the chaos, they still run as well oiled machines at their core. There are habits, rituals, and the business follows a certain rhythm. I believe if you get this right, then you start to define at the unit level what the “perfect day” for an employee looks like which translates into successful weeks, months, quarters and years for the overall business.

I think an entire book can be written on the points above, and for me in my journey, I’m still in the thick of it and living it. What’re you doing as a CEO to achieve the above? Be sure to share your thoughts in the comments section below.