Leader · Trusted Advisor · Business Developer

Jason
Schlosser

My passion is helping good businesses become great ones โ€” by investing in and developing people. Because a healthy culture and healthy revenue are not competing priorities. They are essential.

Jason speaking at an event

A heart for people,
a career built on it

I've spent the last decade building businesses and leading sales organizations โ€” and the decade before that learning the craft of hospitality that made it all possible. The through line in all of it is people. Develop the right people, build the right culture, and the business takes care of itself.

As CEO of Ohana Vacations, I led a portfolio of boutique inns and vacation rentals across Maine, Oregon, Georgia, and Costa Rica. Before that, I led a large sales organization at Vacasa, learning what it really takes to grow a team that performs because it genuinely wants to.

But the resume only tells part of the story. I'm a husband to Brigitte, a father, a follower of Jesus, someone who has served communities in Uganda, and a runner who found the sport by chasing his daughter โ€” and never looked back.

Jason and Brigitte
๐Ÿ“ˆ
Business Growth

A decade of building sales organizations and growing businesses by investing in the right people first.

โœ๏ธ
Faith

A Christian whose belief that every person matters shapes how I lead and how I serve.

๐ŸŒ
Uganda

Service work in East Africa has deepened my understanding of what it means to truly welcome someone.

๐Ÿƒ
Running

Boston. Tokyo. Berlin. Chicago. I came to the sport chasing my daughter and never stopped.

Where I've been

2022 โ€“ Present
Ohana Vacations
Chief Executive Officer

Led full business operations across a growing portfolio of boutique inns and vacation rentals in four markets. Built the right team, the right culture, and the right systems โ€” in that order.

Multi-MarketTeam BuildingCulture
Prior
Vacasa
Regional Director of Sales

Led a large regional sales organization through a period of significant growth, including the company's IPO. One of my greatest accomplishments was watching individual contributors grow into team leaders โ€” that's the kind of impact that matters most to me.

Sales LeadershipPeople DevelopmentTeam Culture
30+ Years
Hospitality
A career built on caring

From property-level operations to executive leadership, I've spent three decades learning that the best business strategy and the most human approach are almost always the same thing. Nearly twenty of those years were spent in sales โ€” growing revenue significantly by building relationships, developing people, and creating cultures where everyone was pointed at the same goal. Take care of your people. Your people take care of your guests. Your guests take care of your business.

OperationsGuest ExperienceCulture

Growing healthy businesses
with happy people

I work with hospitality owners, investors, and operators as a trusted advisor and business development partner โ€” not someone who shows up with a clipboard and a framework. Someone who's been in the room, made the hard calls, and cares about getting it right. The culture and the revenue. The team and the bottom line. All of it, together.

01
Culture & People

Building teams that actually want to be there โ€” through intentional hiring, leadership development, and creating environments where people do their best work and guests feel the difference.

02
Business Development

Finding and creating growth โ€” new markets, stronger owner relationships, and strategies that scale without losing what made the business worth growing in the first place.

03
Trusted Advisory

A thought partner for the real decisions โ€” the ones without obvious answers. Someone who asks good questions, gives honest perspective, and stays in it with you.

What drives me

Jason with his family
Faith & Family

Rooted in what matters

My faith as a Christian informs everything โ€” how I lead, how I serve, how I show up for my family. I'm a husband to Brigitte and a father first. My son Jaidan serves in the Marines. My daughter Ava has become one of my greatest inspirations.

Jason serving in Uganda
Uganda & Global Service

A bigger table

Serving communities in Uganda changed me. It expanded my understanding of hospitality beyond the inn or vacation home โ€” into the radical, simple act of welcoming another person and making them feel like they matter.

Jason and Ava
Running

Boston. Tokyo. Berlin. Chicago.

I came to running late, following my daughter Ava into the sport. It rewired me. Four world majors in and over $30,000 raised for causes I believe in โ€” I'm still lacing up every morning, grateful for every mile.

What people say

Jason has truly impressed with his initiative in seeking constant improvement โ€” personally and professionally โ€” his great leadership and true care for his team and organization, as well as his sincere and laser-focus on helping and serving all of those that are privileged to come into contact with him. As a true believer that the little things are really the BIG things, Jason consistently demonstrates commitment to executing on all of them.

Larry Long Jr, CSP
Global Keynote Speaker & Sales Acceleration Expert

It is not common to work on a team that stays goal oriented and motivated with a clear vision in mind, but that is the exact environment Jason's leadership creates. The market he managed experienced consistent client growth with clear expectations for the decisions necessary to experience consistent revenue growth. It was a great learning experience and I would not hesitate to work under his leadership again.

Ulises Gonzalez
Senior Analytics Professional ยท Colleague at Vacasa

I had the privilege of working with Jason on two separate occasions and I would work with him again if the opportunity ever presented itself. He is ethical, compassionate and trustworthy โ€” always known as a top performer. He can be trusted to make an impact and inspire everyone around him. Jason was never out for himself; he cared about his clients, his team, and the company, and it showed in everything he did. Jason would be a standout in any role for any company lucky to have him.

Yael Livneh
Fractional Sales Leadership & Strategic Consulting ยท Senior colleague at Vacasa

Running as a
spiritual practice

I didn't find running. My daughter did โ€” and I followed her into it. What started as a way to connect with Ava became one of the great loves of my life.

There's something deeply honest about running. You can't fake 26.2 miles. You show up, do the work, and trust the training. I've carried that back into every boardroom and every conversation since.

Four world majors in. Over $30,000 raised for causes I believe in โ€” including cancer research through the Dana-Farber Marathon Challenge and clean water access through WaterAid. The road ahead is always the best part.

Boston MarathonDana-Farber โœ“
Tokyo MarathonWaterAid โœ“
Berlin MarathonCompleted โœ“
Chicago MarathonCompleted โœ“
Jason running the Tokyo Marathon
Dana-Farber Marathon Challenge
Berlin Marathon
4 World Majors completed
$30k+ Raised for charity

Let's have a conversation

Whether you're a hospitality owner looking for a trusted advisor, someone exploring a business partnership, or just want to talk about building something worth being proud of โ€” I'd love to hear from you.

Based in Boothbay Harbor, Maine โ€” and open to working remotely or traveling wherever the right opportunity takes me.