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Creative Digital Marketing Agency, Oak Street Associates, provides customized marketing and consulting strategies to scale your business online.

Growth Focused Solutions

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Image by Sasha Kaunas

Boutique Hospitality Growth & Technology

Drive growth and stronger business outcomes.

Oak Street Associates helps independent hospitality businesses turn opportunity into stronger business outcomes through growth leadership, marketing execution, revenue-driving websites, and practical technology.

Explore Oak Street

Choose the right starting point.

Growth rarely comes from one channel, one campaign, or one piece of software. We help hospitality businesses connect growth leadership, execution, and the systems behind the business so priorities are clearer, marketing works harder, and growth is easier to sustain.

Marketing & Consulting

Strategy and hands-on execution across positioning, websites, demand generation, campaigns, and the marketing priorities that move the business forward.

Technical Solutions

Specialized technology, automation, integrations, and custom software built around a specific operating problem or opportunity.

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Fractional CRO

Ongoing commercial leadership for businesses that need clearer priorities, stronger decisions, and accountability around growth.

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Inn Transitions

Guidance for opening, buying, selling, or preparing for a future exit — with a clearer view of the business, its systems, and the priorities that matter most.

A more connected approach

Growth works better when the pieces work together.

Oak Street combines fractional CRO leadership, hands-on marketing, and custom technology. When you're opening, buying, or selling an inn, we bring that same operating approach to the property transition.

Fractional CRO

Set the direction.

Clear priorities, stronger decisions, and accountability around the growth plan.

STRATEGY · REVENUE · LEADERSHIP

TECHNOLOGY

Build what fits.

Connect systems, automate work, and solve operating problems off-the-shelf tools can't.

DATA · AUTOMATION · CUSTOM SYSTEMS

MARKETING

Create demand.

Position the property, reach the right guests, and turn demand into direct revenue.

POSITIONING · CAMPAIGNS · CONVERSIONS

INN TRANSITIONS

Buying. Selling. Opening. Repositioning.

Bring the business strategy behind the property into the moments when ownership or operations change.

OPENING · ACQUISITION · EXIT

The Oak Street Model

The pieces work better together.

Strategy sets the direction. Marketing creates demand. Technology creates leverage. And when the property itself is changing, we help connect the decisions around it.

What clients say

Work that translates in the real world.

We work alongside independent hospitality businesses to turn ideas, opportunities, and challenges into meaningful progress.

01 – Growth / Strategy

Oak Street Associates helped us see our business more clearly and gave us a practical plan to grow. Their mix of strategic insight, hands-on support, and deep hospitality experience made all the difference. We’re in a stronger position today because of their partnership.
Tiffany G
The South Street House

02 – Marketing / Website

Oak Street helped us take what was already special about the property and communicate it much more clearly. The new direction gave us a stronger story, a better digital presence, and a much more intentional way to reach the right guests.
Tiffany G
The South Street House

03 – Technology / Operations

They took the time to understand how our business actually worked before recommending anything. Instead of adding more software, they helped simplify the process, connect the right pieces, and build a system that made day-to-day work easier.
Tiffany G
The South Street House

Focus on your business & let us handle the rest.

Let's work together.

Whether you’re trying to generate more demand, clarify your growth strategy, improve your digital presence, or modernize the systems behind the business, we can start with the problem in front of you.

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