Oakline President Mark Mason on Alpine’s Investor-in-Residence Program

Tell us about your background and what led you to Alpine’s IIR program.

I started out in management consulting. At McKinsey, I focused on private equity with the goal of moving into that space, and after a couple of years I joined the PE firm Berkshire Partners. Then I went to business school, thinking I’d go right back to large-cap private equity when I was finished. At graduation, I had an offer in hand from a major global firm. But then a young venture firm called SWaN & Legend reached out, looking for someone to help grow their fund.

I like investing, but what really gives me energy is building teams—hiring people, helping them grow, figuring out all the nuts and bolts to support them. Being able to do both of those things at the company level was really appealing. So I turned down the big firm and spent the next seven years helping to build SWaN.

The opportunity to become an IIR at Alpine was a similarly exciting opportunity to build something bigger than myself from the ground up. It’s a truly unique opportunity, as well, because you’re doing it with the resources and expertise of a 25-year firm. You join the deal team as a senior investment professional, with the explicit understanding that is a temporary assignment, and that ultimately you will help launch a new platform and be its President. The role is a strategic partner to the CEO, and you’re overseeing all inorganic growth. So you get a chance to learn how Alpine does deals, you get time to explore what you want to build and to develop an investment thesis—and then you get full support from Alpine in getting the business off the ground and throughout the launch phase of the build. To my knowledge, there’s really nothing like it in the market.

What was the in-residence period like, before you launched Oakline?

I started in September 2024, and it was a few months before we started on the idea that became Oakline. I was helping other Alpine companies work on their own launches and just learning the ins and outs of the process. The team had been explicit during my interviews that whatever I ultimately worked on, it would be opt-in, not just an assignment. So I was very comfortable with the initial period of ambiguity—in fact, I really appreciated that I would be involved in developing the investment thesis. And I knew Alpine had extensive experience finding new markets and building successful companies in them.

I started looking at investment materials in December and gravitated toward the property management space very quickly. I’d had board experience in restaurants, and there are lots of similarities in terms of service and hospitality, which was exciting to me. Amanda and I formed a “pod,” with Matt joining shortly after. By May, we had launched Oakline Properties, which is a national property and association management platform that partners with leading regional firms to scale operations, enhance service delivery, and unlock growth. We started hiring around the same time, and our official launch with Alpine Investors was in September 2025 when we partnered with a southern California-based company called Cirrus Asset Management, which manages 20,000+ units across a more than $7 billion portfolio of both conventional and affordable multi-family properties.

With that deal closed, I’m moving more fully into an operator role, focusing on growth and helping lead Oakline as we pursue our next few acquisitions. Our Big Hairy Audacious Goal is to build the best property management firm in the country for clients, employees and residents.

Tell us about that leadership role. How have these first months of Oakline been for you?

At first it felt a bit like we were still Alpine employees, just working on something new. But as we’ve built out the Oakline team itself, it’s felt more and more like a separate company. And we’ve been able to ramp up quickly, in part because of the support we’ve had from all the smart, talented people at Alpine. The M&A resources are obviously exceptional—we had dedicated support from Alpine’s 40+ person sourcing team, which jump-started our M&A engine before we even officially launched. Aside from help with the deal itself, we’ve had people from Atlas (the Alpine Operations Group valuation creation team) helping stand up our bank account, getting our IT set up—all the blocking and tackling of starting a new business that normally takes so much time away from higher priorities like hiring. That “bear hug” of resources really helped us get off the ground.

Deal execution is a core part of our thesis, and I’m continuing to keep a strong handle on that. But the support from Alpine has allowed us to shift toward the team, including evaluating performance and developing swim lanes and processes. And the firm’s ecosystem has been hugely helpful to our individual team members, too. If you’re a new controller, for example, there’s someone at Atlas whose job is to help you onboard—and there are many people in similar roles across the portfolio who can give you advice.

“We’re starting to see how Alpine’s rhythms and PeopleFirst culture translate to the property management space. It’s really been fun

We’ve been able to grow the team very quickly; our first hire started in June and by August we had 10 people on board. We already have a full finance function, and I’ve been building out our M&A team—they are already running deals in conjunction with the Alpine team, and we expect they’ll be largely independent by early next year. Our leadership team is fully fleshed out and making decisions in consultation with the board. And now that we’re in our own Oakline office, we’re starting to see how Alpine’s rhythms and PeopleFirst culture translate to the property management space. It’s really been fun.

How are you and the team thinking about Oakline’s future growth? What conversations are you having with founders?

We have several deals in progress now and hope to have 70,000-plus units under management within the next few months. That would put us in the National Multifamily Housing Council’s Top 50, which I think would be pretty exciting for our first year. The PeopleFirst approach is a big reason that’s possible—founders care about their employees and want to know they’ll be well cared-for, which unfortunately has not been the norm with acquisitions in this industry.

With Steve Heimler, the founder of Cirrus, we had many conversations about creating opportunities for his team to grow with the business. We’re in talks now with another large, family-owned company that has very similar priorities, and we are probably the only private equity company they’d consider partnering with . Our goal is truly to build a company that takes care of its employees, residents, and owners and that’s a much easier conversation.

What are you most excited about as Oakline continues to grow?

I think we can compete in this market in a way no one else is, in part by doing what other Alpine companies have done to great success. That means harnessing the customer-centricity of regional best-in-class operators, but giving them the benefits of national scale—in terms of training and development, technology, go-to-market (GTM) professionalization, talent sourcing. The possibilities are endless, and we’re excited to help our partners reach their full potential and be bigger and better than they’ve ever been.

On GTM, we’ve already begun. Sales in this market tend to be very referral-based, so Atlas has started working closely with Cirrus to build out a more systematized program. Technology will also be huge for enhancing customer service and satisfaction; we think AI is creating opportunities to reduce some of the administrative burden on team members so they can focus more on serving residents and owners. And in general, as Oakline grows, I expect that will create more opportunities to learn from one another—each company has its own playbook, and we can share best practices to get the best of all worlds across the platform.

We believe that if we provide superior experiences for residents, they’ll be happier and renew more often, which in turn means superior financial results for owners. It’s a virtuous cycle. Ultimately, the goal is that for anyone with a new property in the multi-family space, an Oakline company is the partner of choice. We want to be their natural pick.

About Alpine’s Investor-in-Residence Program

Alpine’s Investor-in-Residence (IIR) program is a first-of-its-kind opportunity for entrepreneurial investors who want to build new companies from the ground up, with the resources and support of Alpine’s 25+ years of experience behind them. The IIR program has two core phases: In-Residence and Operator. During the In-Residence period, an IIR works with Alpine to identify and underwrite the target market for Alpine’s next platform. Then, during the Operator period, an IIR launches and joins the new platform as President to lead inorganic growth strategy and build the business alongside an Alpine-backed CEO. This program offers a unique pathway for operationally-minded investment professionals who aspire to become C-suite executives. To learn more about the program, reach out to Matt Jackson: mjackson@alpineinvestors.com.

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