Christina Martinez has always been committed to impact. As she considered her first career move, teaching felt like the perfect way to reach students right away. So she pursued a role at Teach for America before discovering impact through business with a stint at Google, an MBA at the Stanford GSB, and in multiple management roles for Alpine portfolio companies. Today, she leads a team of nearly 50 at PLANOLY, and spends her days focused on aligning her team around a shared purpose.

Tell us about your background. Have you always known you wanted to be a CEO?

I majored in molecular biology purely because I loved learning about science. That major also taught me how to think, how to be critical and strategic, and how to ask questions. I learned not to take things at face value, a practice I’ve taken with me into the business world. I thought I would get my Ph.D., but after working in a lab during college I decided lab work was not the right fit for me.

The Teach For America (TFA) mission resonated right away. My parents are Cuban immigrants and they came here as teenagers. They left everything behind to start a new life in a country where they didn’t know the language. Then they put themselves through medical school, which I think is only possible when you have a deep belief that education is a critical factor in your ability to make your way in the world. I was raised with the idea that school was my ticket to success, and I truly believe education is a great equalizer.

I truly believe education is a great equalizer.

TFA gave me the chance to move to California for my first job, and teaching remains one of the hardest and most rewarding things I’ve ever done. After spending two years teaching high school chemistry, I decided I wanted to try something in the business world. I loved the scalability of business and the chance to make an impact on more people. So I applied to a sales role at Google on a whim. It was 2011 and the economy was coming out of the recession and starting to boom again. At Google, I learned about customer success, how to sell, and how to collaborate with multiple teams.  After a few years, I decided I wanted broader responsibility at a smaller company. I went to the GSB to gain a more holistic understanding of how to manage a team, how to manage a business, and how to drive strategic alignment between teams—all things you don’t necessarily get exposure to when you’re working in one specific division at a very large company. Those lessons and a desire to keep learning and having clear impact led me to Alpine.

How did you know Alpine was a good fit for you?

I knew Alpine would be really challenging, but I also believed I could be good at leading within a portfolio company. I like managing people, building teams, and coaching, and I really like the holistic strategy aspect of running a small business. But I’m not an entrepreneur; I get more energy from managing teams with some scale vs. starting something from scratch. Alpine seemed like a great way to get me into a position where I knew I could excel—with some practice—without having to spend 10 or 20 years working toward that point. Part of me thought it was crazy that someone with eight years of business experience and a graduate degree could run a company and manage a team. But as I saw other Alpine people run companies, I realized that you have to start somewhere. While the learning curve is steep, after a couple of months I was amazed at what I learned, and Alpine had my back the entire way.

What was your first Alpine leadership role, and what lessons did you learn that you carry with you into your CEO role?

I started as CMO of the behavioral health vertical in Alpine Software Group (ASG). I got a chance to hire some really great people, to figure out a big strategy across three different businesses, and to interface with many of our individual CEOs.

Starting on day one I knew I needed to prove my worth. I had some business experience and a degree, but I hadn’t worked in the space previously and I had never held a C-level title before. It was really important for me to build relationships by learning about the team and helping them learn about me. I wanted the team to know that I had good intentions and even though I wasn’t experienced in the space, I could bring a different way of thinking about things—like the sales process. I also got really good at having conversations I probably would have avoided in prior jobs. The more I practiced resolving tension on the spot, the easier it was to have those difficult conversations.

Why did you move from ASG into your current CEO role?

Steve Reardon—CEO of Traject at the time—and Traject’s current CEO Alice Song approached me because they wanted strategic help in building a few of their products. They also shared that since Traject does so many acquisitions, I would likely have an opportunity to run a business in the MarTech space. With the CEO goal in mind, I joined the Traject team as Chief Innovation Officer working on two of their products. Eight months later, Traject acquired PLANOLY—a social management tool for Instagram and Pinterest that allows users to visually plan and schedule their content—and I jumped at the opportunity to lead the team. PLANOLY’s previous CEO and founding team were looking for a buyer that would allow them to exit quickly, so I joined as CEO in November 2020, three days before I got married.

What do you love about PLANOLY and about being CEO?

PLANOLY moves quickly. We’re very data-driven, we have a lot of customers, and we’re in constant motion. We can measure the impact of small changes to our app or website because we have so much traffic. I felt at home here right away. I love the fact that we can make quick decisions based on the way users are actually interacting with the app.

Being CEO feels like a wide set of open opportunities, and it’s also a big responsibility. There’s so much we can do to increase the number of customers on our platform, to improve our software, and to help people grow in their careers. That potential can feel exciting—and overwhelming. PLANOLY was already growing and thriving, now it’s my job to keep us on a successful track.

Who do you lean on for support?

My leadership team is awesome and we’ve developed a good relationship very quickly. The CEO role is much less lonely when you have people on your team who have your back. ASG also set up CEO pods, so I talk to four other ASG CEOs every month; we share what is happening and listen without judgement. I really value getting other people’s thoughts, and we have fun without taking things too seriously. There’s also a Slack channel where all the ASG CEOs can post questions and ask for advice from one another, because usually someone else has already experienced what you’re working on. I recently asked for a sample job description and someone from Paradigm sent me theirs. It’s really helpful to not have to recreate the wheel.

What are you focused on right now?

We’re having ongoing conversations around KPIs and what matters, and we’re really focused on retention. Our customer base (mostly individuals) moves a lot more than an enterprise business’ customers would, so we have to make sure we keep our existing customers, while still working to gain new ones. 

We’re also going through the one page planning process right now through Alpine’s PeopleFirst program. I love aligning the team around a mission and vision that matters, and then seeing how that translates to annual and quarterly goals. There are eight big initiatives that we’re focused on this quarter, and almost all of them relate back to that north star of improving customer retention. We report on those initiatives at All Hands meetings, and I can see the team getting energized by working toward a shared goal. In December we shared a memo about the things we care about, including new customer additions and retention and the numerical goals for each. We got 65 thoughtful proposals about initiatives we could take on to address those goals. It was a great way to engage the team and as a new CEO, it really helped me dive in and identify ways to make an impact.

What areas of personal and professional growth are you working on?

I tend to be a little bit more reserved, and I’m really trying to let people get to know me. Especially as a new CEO joining during a pandemic, most of my interactions happen over Zoom. It’s so important as a leader for people to know who you are and what you value. I got feedback early on that I wasn’t doing enough small talk at the beginning of company meetings, so now I kick off meetings with a question or story, something like, “Share something you’re doing for your own wellness this week.” People start to engage, and sometimes it’s a bit awkward, but it helps us ease into the meeting. Our VP of People also suggested we add an “Ask Me Anything” portion to our team meetings. As a new CEO, the team wants to know who you are. But working remotely means we don’t have opportunities for organic interaction which has been really tough. I have to think about improving my connection a bit every single day, but it’s getting easier. 

How do you continue to work with Traject even as you focus on PLANOLY?

We have the perfect setup. I talk to the Traject CEO almost every day, and then I frequently attend their weekly leadership meetings. Having that relationship from my time at Traject makes it much easier to collaborate. I also love the way we have integrated the important things, like finance and administrative functions, but maintained our own core teams focused on things like the product. Our marketing, customer service, and technology leaders are connected but not combined, so everyone can learn from each other and expand their networks. Traject already has a social media management tool in a slightly different space, and I’m excited to think through ways we might either cross-sell or upgrade customers from one tool to another to keep them within the Traject family.

What’s next for you and for PLANOLY?

We’re kicking off Alpine’s PeopleFirst alignment program, beginning with the passion and purpose sessions. I’m really excited for the team to reflect on their work and our team’s direction. I think it will help us align around our goals for the future of PLANOLY, and then we can pursue that direction together.

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