Lori Stephens
What did your journey to Checkmk look like, and what specifically excited you about the role as Renewal Specialist when you first joined us?
I discovered early in life that the only thing I loved more than buying shoes was selling shoes…my sales journey quickly evolved from sneakers to medical systems. With almost two decades of managing Sales Operations and Support in the construction and facility compliance environment, I found my happy place between curating relationships and analysing sales data.
When the role with Checkmk presented itself, I jumped in headfirst. An established company with an outstanding reputation, carrying unbound potential to a new yet flourishing North American team is an opportunity that I’m still really excited to be a part of.
If you had to describe your typical workday: What are your main responsibilities in the US team, and which tools make your life the easiest?
My primary responsibility is managing license renewals and billing for our North American customers, although I also have a hand in office administration and anywhere else I’m needed. I’m heavy on spreadsheets due to a deep disdain for math, so Excel/Sheets and a notebook (probably showing my age) will always be my primary tools. I also rely daily on knowledge databases put together by the Checkmk gurus; being newer to the world of IT monitoring, it’s been a lifesaver. But nothing has been more integral than the support of our brilliant Consultants, Ops, and Sales teams around the world.
In your position, you contribute significantly to our US renewals and support team. Which recent project did you enjoy working on the most, and why?
Our customers are great, really great; I’ve enjoyed getting to connect with so many! If I had to narrow it down, I’d say working with our partners at FirstLight has been notably fulfilling. The door was opened to foster relationships with their renewal coordinators and introduce them to our growing AE team (who have masterfully done the heavy sales lifting!), along with simply refining processes for mutual-efficiency along the way. Like planting a garden, we all play our part to sow and toil, so it’s rewarding to harvest together.
Every role has its own hurdles. What do you consider the most exciting challenge in your job right now, and how are you tackling it?
Expedient growth…the best of all problems. Our team is expanding and our customer base is broadening. We assessed the challenges ahead of us and a good foundation was laid to allow for successful takeoff, now we’re headed to the moon!
At Checkmk, we place a lot of value on team spirit. What do you appreciate most about working with your immediate team, and what does collaboration with other departments look like for you?
It doesn’t take much time with the US sales team to learn that we’re an adventurous, dedicated, and competitive group! Coming from a full spectrum of cultural and professional backgrounds, we learn together, teach and motivate each other, and have had a ball doing it. Being surrounded by people who laugh as loud, commit as fully, and care about the team and our goals as much as I do is invaluable to me. We’re always rooting for each other, but we’re still going to race to the top of the stairs!
I also have the unique pleasure of getting to connect with colleagues in Operations, Finance, Marketing, Legal, and People & Culture for various responsibilities and ad hoc missions, who are all equally fantastic to work with. Communicating with teams across the board has afforded the insight of overlapping interdepartmental processes, which is important to my process-centric mind. On a personal note, I’ve sincerely enjoyed getting to know everyone and could not begin to thank them all for answering my many, many, many questions!
When you're not busy working on supporting customers and renewals, what does your perfect evening look like to clear your head and unwind?
Let me water and talk to my plants without judgement, give me some room to run around with my dogs, then watch a movie with my boys and I couldn’t ask for more.
Do you remember a particularly interesting, exciting or beautiful experience you had at Checkmk? If so, can you tell us about it?
The 2026 Checkmk Conference in Munich was a meaningful trip, definitely for me but also for our team. Being able to take part in so many new and exciting things with so many incredible people is something I’ll always hold onto. Grateful for the exhaustive efforts by all the teams who put this amazing global event together, and still hosted and treated us like family. Prost!