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“When someone tells me something is not possible, it serves as an incredible energy source for me” With Smartsheet CEO, Mark Mader

…“Tell me it’s not possible.” I always appreciate the push I get from a naysayer, even though it often feels like something other than…


…“Tell me it’s not possible.” I always appreciate the push I get from a naysayer, even though it often feels like something other than appreciation in the moment. That’s because when someone tells me something is not possible, I work to keep my external reaction tempered, but it serves as an incredible energy source for me — every time.


I had the pleasure to interview Mark Mader. Mark serves as President and CEO of Smartsheet, a high-growth software company transforming the way organizations plan, track, automate, and report on work at scale. Based in Seattle, Mark leads a high-performing team of over 800 employees bringing to market a SaaS platform used by millions of people at over 74,000 customers, including more than half of the Fortune 500. Mark is a recognized leader in the technology community, having been named Ernst & Young’s Entrepreneur of the Year in Technology for the Pacific Northwest, and GeekWire’s CEO of the Year.

Thank yo so much for joining us! What is your “backstory”?

I’ve worked in software for over twenty years, starting in CRM and now in the category of work management and execution. The companies, solutions offered, and roles have always served business users. Throughout, I’ve seen the delta between what many software companies say their software does and the extent to which customers actually realize those benefits. I have always strived to find ways to mind that gap and empower people, regardless of their technical skills, so that they can realize a software offering’s full potential.

I became a SaaS believer during my time at Onyx where I oversaw the consulting and customer-facing teams in the Americas, Europe, and Asia. I watched hundreds of well-intentioned customers cope with deploying and managing installed or self-hosted software. I was blown away by the increased velocity that SaaS enabled and how it seemed to lower both cost and stress levels for the people using it. That brought me to my role as President and CEO of Smartsheet, where I lead a high-growth work execution software company improving the way organizations plan, track, capture, automate and report on work, serving over 75,000 customers globally.

Going back a few years, I went to Dartmouth intending to study Economics but pivoted when given the opportunity to work with a tremendous professor whose curriculum seemed like the perfect balance between theory and practical application.

A Geographic Information Systems (GIS) class I took junior year was my first in-depth exposure to tech being applied to a high impact use case. Yes, Geography extends far beyond knowing the location of countries; it includes business concepts like location decision — making data-driven decisions with the help of layers of data sets such as infrastructure, labor, tax, natural resources, proximity to universities, and any other attributes relevant to the placement of a particular company. It showed me how critical thinking combined with data and software can lead to better insights and outcomes. When my leadership team and I were considering where to open Smartsheet’s second major office, we created a sheet with 16 variables that included everything from educational landscape to proximity to major customers to the maturity of the software market, among others. That took me right back to my GIS class (we chose Boston, by the way).

I have also been fortunate to spend a lot of time overseas. It has provided me with firsthand experiences that allow me to appreciate that differences in beliefs and approach shouldn’t be perceived as obstacles, but can make for a richer experience. I grew up in Germany and in my professional career have had the opportunity to build and lead teams throughout Europe and Asia.

Can you share the funniest or most interesting story that happened to you since you began leading your company?

The story that stands out is from when Smartsheet was in the early days, around fifty people. I received an email from a customer in Shanghai, asking me to help support her small clean energy company. She wasn’t in a position to spend much but we allowed her team to use our platform for a nominal fee, around $300/year. She was ecstatic.

And as it turns out, we have strong evidence that her company was the first to expose Smartsheet (through the online sharing of work) to what is, today, our largest customer.

It’s an improbable story and the example I use when highlighting the connected nature of the world we live in. It’s served as a great lesson for our team: you will never have perfect visibility into a customer’s network of influence and impact, so treat everyone with respect and empower them. Make the investment.


How do you synchronize large teams to effectively work together?

Large teams should be synchronized on the overall mission and objectives, but it’s important not to fret about being “fully synchronized” at every moment. When companies or teams become overly concerned with the synchronization of every single detail of a project, it can hinder velocity and creativity, which flies in the face of decentralized decision making.

I prefer to focus on the connecting parts and making sure teams know their “service levels” to one another. Then, on a repeating cadence, teams report out to one another — not just up the line to senior management. “Reporting out” is fundamental to being aware of where people are stuck and what they can do to unblock a peer. It is incredibly empowering, especially in a software company where the interdependencies are vast. The degree to which teams use software to their advantage, so that reporting out can be automated or self-service, directly leads to higher velocity and employee engagement.

What is the top challenge when managing global teams in different geographical locations? Can you give an example or story?

The biggest challenge is making each team and team member feel as important and central to our company mission as the next. It’s about enrolling and engaging people in field offices as much as those who work at “HQ.” Two important mechanisms to achieving this include ensuring that leadership is present and engaged in the field on a consistent basis and continuously soliciting stories and insights from the field. Very often, team members not located at headquarters are in a better position to identify and relay customer signal.

One of the ways we bring that mindset to life is with an office visits calendar to ensure we have a regular, planned cadence of leaders traveling to our major office locations. A senior executive is in every one of our offices at least once a month, enough to maintain connectedness but not so often that the teams feel overwhelmed by a flood of visitors.

We also have an internal platform for employee engagement, powered by Workplace by Facebook. In their digital form, the offices looks the same. Our Bellevue team, which is 50x the size of our Edinburgh team, looks identical in its visual weighting. It’s a small detail, but important. I also try to set the right tone in how we communicate. You won’t see me post about how excited I am for an upcoming Bellevue team offsite without also recognizing sister events taking place abroad. When a meaningful number of employees are not able to participate due to location, it’s important to be mindful when highlighting things they can’t participate in.

What advice would you give to other CEOs or founders to help their employees to thrive?

My advice is to set guidelines, not guardrails — and then empower your team to go out and execute.

Stating your company values is important, but living them through actions in an authentic manner, every day, is what has impact. That’s what I try to get across to my team.

Most times when people quit their jobs they actually “quit their managers.” What are your thoughts on retaining talent today?

People have incredible choice today and that places a healthy pressure on companies who want to provide a great experience. Bad news can travel fast, but there are also mechanisms for building a great reputation. And I believe actively managing brand reputation through team awards and online reputation sites is important.

I would also argue that the “people quit managers” point of view may have been more valid 5–10 years ago. Today I believe it is very much a balance between strength of manager and belief in company mission.

My team and I spend a lot of time thinking about how we invest in our company culture and community. One way we make this real is through an ongoing speaker series for employees. A recent guest speaker was Kim Scott, author of Radical Candor, who coached our company on how to develop a strong platform for communication and feedback. We had to invest to make this happen, but it was well worth that investment. The importance of doing what it takes to build loyalty cannot be understated.


Based on your personal experience, what are the “5 Things You Need To Know To Successfully Manage a Team.” (Please share a story or example for each, Ideally an example from your experience)

1. Know what you need/want — (Poor) leaders often point to their team when something doesn’t go to plan. Before assessing blame, check in with yourself. Did you set clear expectations about what the desired outcome would look like?

2. Diversity in experience — Aim to build a balanced team through culture “adds,” not just culture “fits.” Hiring for excellence is a worthy pursuit; just make sure that excellence does not equate to sameness.

3. “The Spokane test” — Experience is important. Skills are important. But we also ask ourselves a question about every candidate: “could I spend time with this person on the 250 mile trip from Bellevue (our headquarters) to Spokane?” The idea being that you may have an incredible resume, but if you’d be a mighty challenge to spend five hours with in a car, shoulder to shoulder, you may not be a great long term teammate. There is a balance to strike between bringing fresh thinking and considering whether the candidate is additive to our values and culture.

4. Fairness and consistency — This one can be tough in practice. Of course we celebrate when good things happen and feel disappointment when they don’t. But when I say consistency, I mean keeping emotions in check. Not every big win warrants a mega-celebration. Likewise when encountering serious issues, we don’t wilt or feel defeated. I encourage my team to temper both their enthusiasm and disappointment so we can better weather the inevitable ups and downs of any business.

5. Give more credit than you take (without going over the top) — Some managers give their teams too little credit, which most of us recognize as negative behavior. But others err on the opposite side and take absolutely no credit for themselves, which can feel disingenuous when everyone knows you worked on the project. We should recognize great work without being so effusive and deferential that we lose credibility.

If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

I have a passion for empowering people who are less technically proficient. I love the idea that technology can enable individuals who previously believed something wasn’t possible and then accomplished it. I’ve seen self-limiting beliefs like “I can’t do it because I’m not a coder” or “it’s too complex” hold too many people back.

That’s why our team at Smartsheet works hard to help people discover what is possible and to change the mindset of those who believe they’re “behind” in some way.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Tell me it’s not possible.”

I always appreciate the push I get from a naysayer, even though it often feels like something other than appreciation in the moment.

That’s because when someone tells me something is not possible, I work to keep my external reaction tempered, but it serves as an incredible energy source for me — every time.

Originally published at medium.com

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