Darin, Mike, and Mark leading a meeting on the Jackrabbit Technologies company retreat.

Establishing Credibility as a Leader

The journey of a new COO joining an established software company.

Hi, my name is Darin Soll, and I’m an Integrator.  Not in a technical, connecting systems sense, but in a leadership, creating harmony sense.

For the past ten years, I have been helping small software companies grow.  When I discovered Jackrabbit Technologies this past Fall, I was intrigued–here was a fast-growing, 14-year-old software company that was still led by its co-founders.  Yet somehow, nothing was on fire and no one was running for the exits.  Anyone who has worked with bootstrapped technology companies knows that this is atypical–scalability challenges are notorious for sucking all the fun out of growth for entrepreneurial founders.

Jackrabbit was seeking a COO to take over the responsibility of day-to-day operations so that its CEO, Mark Mahoney, could focus on strategic matters, the subject of his previous blog post.  I really liked the team and its extremely appealing culture, and I felt my experience leading software companies through startup-to-growth stage transitions would be an asset to Jackrabbit.  

I joined the company in mid-October.

So how does one go about inserting himself between the CEO and the existing leadership team?  Very, very carefully…

I began developing relationships with each member of the Jackrabbit leadership team to better understand their organizations and responsibilities.  In that process, I noticed that Jackrabbit’s co-founder, Mike Carper, was significantly overloaded, personally wearing Product, Engineering, Infrastructure, and internal IT hats.  After engaging Mike in a series of conversations about this challenge, we quickly developed a rapport and presented our initial vision to his team.  Mike and I were able to move quickly from vision to planning, setting the stage for dividing his organization into separate Product and Engineering teams, each with dedicated leaders.  This organizational change is in progress.

Because of my operations leadership role, I also took over the reins of an internal Jackrabbit project to implement the Entrepreneurial Operating System (EOS), a practical framework for leading and operating businesses.  EOS defines distinct Visionary and Integrator roles.  The Visionary, our CEO, Mark, is the strategic thinker, the big idea person.  The Integrator, our COO, me, is the execution guy.  My role is integrating, or providing the glue, for Jackrabbit’s leaders and teams to work together harmoniously.  

When you think about my role as Integrator, what better way to continue the process of integrating than to meet with every employee?  So, as part of my ramp plan, I met one-on-one with every single employee and contractor at Jackrabbit.  What did this look like?  46 meetings, 40 face-to-face, over 90 days.  I had the opportunity to hear, first-hand, what Jackrabbit employees are passionate about, what they are concerned about, and what we can do as leaders to help them improve.  These meetings were an essential first step in developing trust with a 100-percent remote workforce.

I also met face-to-face with ten Jackrabbit clients, shadowed jumpstart (implementation) calls, and attended our BOOST/West user conference in November for first-hand exposure to the voice of the customer, and to meet key business partners.  Continuing these efforts is essential to establishing myself as a trusted partner and thought leader in the industries Jackrabbit serves.

By mid-December, I began facilitating Jackrabbit’s leadership meetings, and in early January I assumed formal responsibility for all areas of Jackrabbit’s operations except Finance, which remains with Mark for now.

At our annual employee retreat in February, an employee asked me, “What has been the biggest surprise regarding the Jackrabbit world?”  I responded that the company’s overall stability, which again is atypical for a bootstrapped company at this stage, surprised me the most.  The scalability challenges are there–we brush up against them more and more frequently as we grow–and staying ahead of them while preserving Jackrabbit’s very appealing culture will be my biggest challenge going forward.

Speaking of going forward, Jackrabbit is in the process of hiring for 15 new positions, including the Product Manager and Engineering Manager I mentioned earlier.  Creating growth opportunities for our team members is one of my personal passions, and I am very excited that we have recently promoted a number of them into new, expanded roles.  And, our HR team has developed a strong pool of candidates to fill the remaining openings and backfill the positions vacated by promotions.  Expanded roles and new team members bring a renewed level of energy just as we begin to tackle our 2018 objectives.

In 2018, Jackrabbit will continue to deliver high-value software enhancements and the industry’s best support while behind the scenes, we make the right adjustments internally to scale how we lead, how we organize, and how we operate.  Success in 2018 positions us to grow without chaos…in other words, putting the fun back into growth!  Echoing the theme of our annual employee retreat, the future for Jackrabbit is so bright, we have to wear shades!

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