CCBJ: Dan, it’s been a while since we’ve caught up. To start us off, please share some insights about your background and your transition from Sprinklr to Guild?
My career path has been unpredictable and unplanned, meaning each transition I’ve made has been to pursue an unexpected opportunity that presented itself. Coming out of college, I worked in politics for a number of years, and then went back to law school and did the law firm route for about five years before joining the governor’s office in Massachusetts. Then, spent some more time at a big law firm and ended up feeding 10 years of my life to law firms before I was ... I like to say saved, although I’m not trying to throw any shade on the law firm world. It wasn’t for me; I spent more time there than I probably expected to coming out of law school.
I was offered an opportunity to join a client, Athenahealth, to build out a federal affairs program there. I was seated in the legal department thinking my career as a lawyer was over. And it turned out it was really just starting, or it was rebooting. Shortly after I started, I took over responsibility for litigation, then was asked to be acting general counsel when the general counsel went on sabbatical. He left for another opportunity during that period of time, and I ended up general counsel of a publicly-traded company long before I was qualified to be general counsel of a publicly-traded company That experience really gave me a taste for working for a mission-based organization.
Athenahealth exists to save lives by providing information to caregivers when they need it. I had a wonderful career there, moving from being general counsel to chief administrative officer where I had the privilege of overseeing all the people functions of the company, as well as the legal teams.
When the company was taken private by an activist investor, I and many others moved on. I then spent three-and-a-half years at a terrific marketing tech company called Sprinklr. During that time, I had the opportunity to help take Sprinklr public, which was a wonderful learning opportunity.
Then, when Guild reached out, I had the comfort of being able to leave Sprinklr to pursue an extraordinary opportunity with another mission-based organization. Fortunately, my succession plan worked perfectly, and my successor was ready to take the reins. I probably would’ve lost him if I hadn’t gotten out of his way. It was a win-win-win for everyone.
In serving as general counsel and corporate secretary, how have you perceived your role as leader, influencer, and supporter of the success of your company?
I try not to use cliches if I can help it, but sometimes they seem unavoidable. One that applies here is I think of myself as an executive first and a lawyer distant-second. As part of being an executive, I am co-responsible with my peers for setting the direction of the company and helping contribute to strategic decisions. And I work to achieve that by leveraging my legal-based experience—not just legal learning, my subject-matter knowledge—but also what I have observed and experienced.
Somehow, I evolved from a young, unqualified general counsel into a greybeard, literally, who has quite an experience set at high-growth companies, navigating the various business and legal challenges that arise. I’m leveraging that perspective with the intent to further business objectives, be an enabler myself, and build a team of collaborative business enablers. The most important role of any executive is to build a strong team with a strong culture that is aligned to the culture and mission of the organization. A leader must create a team that works first and foremost to make doing business easier and more pleasant for our stakeholders.
Human resources and talent management often fall into the suite of responsibilities for corporate legal executives. What is your advice to others looking to build, develop, and retain high-impact teams throughout their organizations?
That is right in the sweet spot of my career and my experience. Athenahealth offered me the opportunity to expand the scope of my role from overseeing the legal and compliance functions to the tremendous privilege of running all of the people organizations. That included HR, talent acquisition, learning and development. It was a wonderful experience to have relatively early in my career because it goes directly to what I think you’re getting at.
As I said before, every executive’s core responsibility is to build a great team. That’s true in any organization of any significant scale. In order to do that, you really need to be consciously focused on your team at all times—on their individual and collective ambitions, as well as the culture that exists between and among team members.
Leaders should be focused on building organizations of people who are mutually supportive, who have fun at work, who approach their day with a smile, and their stakeholders and their challenges with a smile.
I personally believe, even in the legal context, where often you think of a lawyer as serious, hard-nosed, maybe even cynical, that it is a superpower for a lawyer to be open, optimistic, cheerful. I try to impress that on my teams. It’s been a characteristic of the teams I’ve developed, now at two companies, and what I’m hoping to contribute to now at Guild.
Guild offers ta perfect alignment between my own philosophy and the mission of the company. The company exists to create opportunity for skilling, learning, and career growth among the nation’s workforce—largely people who haven’t traditionally had access to these opportunities.
In essence, the company exists to continuously lift people up, and that is what I aim to do with the teams that I’m privileged to work with. I can look at my teams and say,
“We are doing, on our team, what Guild exists to do in the broader world. Let’s make sure we’re walking the walk amongst ourselves.”
What is your advice to other C-level executives and directors looking to empower their fellow executives with both grit and empathy?
I believe grit follows empathy, and maybe that’s counterintuitive, but grit without empathy can be a negative force. It’s hard to bring people along if all you’ve got is grit. It’s hard to inspire people who don’t believe you care about them. It’s hard to build the trust necessary. One of my favorite clichés in people management is, “Hire people who are smarter than you are.” There’s a whole raft of clichés that capture the sentiment. “If you’re the smartest person in the room, find a different room.” “Hire people who are capable of taking your job and want to do so someday. And then when they’re ready, get out of their way.”
It’s difficult to build the trust necessary to do that if you’re focused entirely on the grit and individual ambition, without the empathy component. It’s important to think about your coworkers’ ambitions and needs as well as your own, to be mutually supportive and empathetic, particularly in difficult contexts like high stakes negotiations or litigation. You need to remember that everyone you’re dealing with is a human being who’s dealing with something. And you don’t know what those things are, but if somebody’s coming across as less than their best self, there’s probably an explanation for that. So not just powering through that but reminding yourself that the way you interact with people matters in terms of the outcomes that you’re able to achieve both individually and collectively.
Dan, you are a two-time cancer survivor and a two-time Ironman triathlete. How does your personal experience influence your particular leadership style?
I’ve been asked this question before, and I’m going to tailor my answer a little bit to the rest of our conversation. I think it takes a measure of grit to get through a cancer diagnosis, to state the obvious. I remember driving my grandmother to the Dana-Farber Cancer Institute in Boston for her own cancer treatments. We would walk into the waiting room and she would target people who looked sad or scared and sit down next to them and chat them up. She would always say something along the lines of, “Chin up. Attitude matters.” Then we’d walk out and she would tell me, “That one’s going to make it,” or, “That one isn’t,” because your mental state matters so much to your physical state.
At that time, I could not imagine I was going to deal with cancer not once, but twice. During those times, her voice always came back to me and the notion that your mental state matters to your physical state. Circling back to your earlier question, what my grandmother was showing in those situations was a tremendous amount of empathy in furtherance of providing a little secondhand grit to people.
The obvious connection between that and the Ironman is I came out of my second cancer diagnosis and my oncologist told me, “Cancer is not going to kill you because we’re going to watch you for the rest of your life and if it comes back, we’re going to see it and we’re going to kill it. But you’ve been irradiated so many times over the course of the decade through treatment, that you’re at a materially higher risk for heart disease and lung disease. The way to even out those odds is to get yourself into really good cardiovascular condition and stay there.”
I began doing endurance events and on a whim—which is a silly thing to say but is true—signed up with a friend for a full Ironman. I’d never done a triathlon. I know it’s not literally true that you can do anything you set your mind to, but I do think it is literally true that most people can do a lot more than they think they can. I never would’ve thought I was capable of an Ironman until I learned that I was. The combination of those two things—the memory of how my grandmother handled her own cancer diagnosis, her treatment, and her empathy, along with how completing two Ironman triathlons has convinced me that you can think you’re exhausted and you still have more—have shaped my leadership style.
The mental lift of achieving extraordinary things is worth the effort. I don’t reference those things often, explicitly, but I do think to your question, how does it inform my leadership style? I try to consciously be empathetic and always conscious of the fact that people deal with more than any of us ever know. And second, I try to instill in my teams this notion that hard things are worth doing and with sustained effort, particularly together, we can often achieve a lot more than we’d expect.
Any final thoughts to share?
I would like to punctuate what I said about the alignment of Guild’s mission to unlock opportunity for the workforce with what jazzes me about being an executive and a people manager.
To go back to my answer to the first question on my path to Guild, it’s also my answer to the “Why Guild?” question for me. I was happy at Sprinklr. I loved my team there. I loved my colleagues there. I could have been very happy just staying at Sprinklr. But I couldn’t pass up the opportunity at Guild, to be a part of a B Corporation that is literally living the maxim, “Do well by doing good.” I don’t like when people use the word “literally” and they don’t mean literally. I mean literally Guild does not do well as a business unless it does good in the world. That is how we make money.
I just love that. It gets me so energized. And I love that in making the move to Guild, I was able to lift the careers of the people very tangibly at Sprinklr who I had brought there, and who down the line of succession, seamlessly moved into better roles and the next steps of their careers.
Published June 1, 2023.