3 Critical Steps for Scaling Your Culture

Dan Phillips
Co-founder & Chairman of the Board


One of the ironies of a venture capital backed startup is that you work in a startup because you love the ability to work closely with a small team that enables you to move fast, make decisions quickly, and create a non-political environment. But you also work in a startup so that you can grow your company into a very successful organization and either go public or get acquired. In either case, your goal is to turn your stock options into a pile of cash!

So, how do you get the best of both worlds? What’s the path you follow to grow your startup into a large company and, at the same time, retain your entrepreneurial spirit, creativity, and maniacal focus on growing the business? In a nutshell, you have to define and execute a plan to scale your culture.

Core values

"In a nutshell, you have to define and execute a plan to scale your culture."

Last week I had the distinct honor of attending the BBJ Best Places to Work Awards ceremony where our company was named a winner for the second year in a row. There were a lot of great stories about success and how they arrived at their destination. But I thought I would share what my experience has taught me and how we go about successfully scaling our CloudHealth Technologies’ culture. There are three critical steps:

#1 - Break out the main principles of your culture.

On the surface, it sounds obvious and should be easy. However, this takes thought from the leadership team and requires an ongoing concerted effort to not only focus on the principles, but to also incorporate them into your daily practice and work ethics. When we started CloudHealth Technologies, we defined our main principles as:

  • Mentorship
  • Agility
  • Ownership
  • Participation
  • Transparency
  • Customer

A previous blog I wrote, CloudHealth Tech Culture – Our Code to Success, talks about this in more detail.

#2 – Identify the key driving initiatives that reinforce your company principles.

These are the specific courses of action you will follow when building your organization. As an example, CloudHealth Tech defined our driving initiatives as:

  • Mentorship: We hire employees who want to learn how to successfully grow a startup and build their careers in the venture capital backed startup ecosystem in the Boston area.
  • Agility: Our team builds processes across all functions and departments to measure and execute short-term goals, while keeping an eye towards the long-term vision. Our process focuses on continually learning, iterating, and improving.
  • Ownership: The personality types we hire thrive on ownership, and we empower them to find solutions to the problems they encounter.
  • Participation: Department meetings are open to everyone, and we encourage opinions on all topics, regardless of individual roles.
  • Transparency: We are transparent with data and constantly explain why we make the decisions we’re making. We share the sales pipeline, product roadmap, financials, marketing strategies, support tickets, and more.
  • Customers: Our customers are why we are here. They are our focal point. Everyone in the company interacts with our customers in some format. We participate in sales, support, and product feedback calls, marketing events, and more.

#3 - Institute culture scale programs to enable your principles to flourish.

As your employee headcount grows and locations expand, this becomes a critical component in maintaining the culture you originally envisioned. Some of the programs we’ve implemented at CloudHealth Tech that align to our core principles include:

  • Mentorship: I personally continue to interview virtually every employee before we hire him or her. The point is not for me to say “yes or no,” to the hiring decision…the point is for me to make the statement that it is critically important for CloudHealth Tech to find people that want the mentoring experience we can provide. And, to make sure the candidate wants this full immersion and the career opportunity we can provide.
  • Agility: As we grow, we are reorganizing every department into many small teams with the ability to make decisions and execute. We now have team leads driving small engineering teams that are project focused. These engineering leads will change teams as projects are completed and new ones begin. We also have BDR leads that we’ve hired, or promoted from within and mid-level managers in all departments.
  • Ownership: We have instituted CloudHealth Bootcamp for all new employees to get them acclimated quickly. Every department has its own documented onboarding process to immediately engage new employees, have them assume ownership for a project, and become productive as quickly as possible. Part of this onboarding process also includes the understanding that each new hire graduating class is expected to take some responsibility in making sure the next class is embraced and onboarded into our culture.
  • Participation: Because we are now approaching hundreds of employees across multiple locations, we have significantly expanded our space. We’ve had to accommodate meeting room overflow and upgrade our remote online meeting capabilities to account for hundreds of participants. Our goal is to make sure our remote employees feel as connected as possible, and that they share the same culture experience as we have in our Boston office. They are encouraged to visit our headquarters often, and we have an ongoing commitment to visit them on a regular basis.
  • Transparency: In addition to opening departmental meetings, we continue to hold a two hour company meeting every 60 days where we share our metrics, what’s working and not working, upcoming objectives, and where we are looking for input…basically everything. After the meeting we have dinner, “refreshments,” and just enjoy one another’s company. We’ve also reached the point where we now have an extended executive staff meeting every three weeks that includes additional management team members.
  • Customers: We have customer engagement programs to ensure that new hires interact with our customers and understand their needs. For example, new hires in engineering are scheduled to participate in customer account management calls conducted by our technical account managers and solutions architects. Engineers are also assigned customers to provide them with a Health Check Service through the use of our platform.

Final Thoughts

The bottom line is that if you are a successful startup, your culture is a big part of what got you to this point of scale. It embodies your corporate identity and should be protected and nurtured. As you grow, you will continually need to adjust your driving initiatives and programs to allow your culture to continue to flourish. But never lose sight of the principals you originally defined that got you here.

Happy hiring.