About Hospitality Navigator

Hospitality Navigator is led by Jess Olivito — strategist, systems thinker, and guide for hospitality businesses seeking clarity, alignment, and confident decisions.

I work with restaurant and hospitality leaders who are carrying pressure — financially, operationally, or culturally — and help them understand what’s really happening inside their business so they can choose the right next steps without the noise, drama, or guesswork.

Meet Jess Olivito

Hospitality Navigator

With more than a decade of experience working with small businesses and hospitality teams, I excel at seeing connections others miss — between people, pricing, performance, and profitability.

I am deeply familiar with the unique challenges hospitality businesses face because I’ve lived them, studied them, and helped others navigate them. I help leaders:

  • interpret their financials with confidence

  • identify where money is leaking

  • align team roles and staffing for better performance

  • build actionable strategies rooted in reality, not hype

I thrive on thoughtful conversation, grounded strategy, and helping businesses move forward with clarity. My work is calm, direct, and practical — designed for people who want answers, not noise.

How I Work

I provide project-based, strategic guidance — not ongoing marketing management. My focus is on helping you see what’s really going on and decide what to do next.

Clients come to me when they:

  • feel overwhelmed by conflicting priorities

  • aren’t sure why the numbers don’t add up

  • need alignment across people and process

  • want clarity before committing to a next step

I don’t offer open-ended social media posting, and I don’t sell “nice-to-have” packages. My work is intentional, finite, and rooted in real business improvement.

Trusted Creative Collaborator

When creative execution is needed — for visual assets, layout, or imagery — I collaborate with Vicky Hallberg, an artist and photographer with a thoughtful eye for design. Vicky works under my direction on scoped projects that support a clear strategy, not as a member of an agency team.

This ensures every visual element reflects your story and purpose — without distracting from the strategic work that actually moves your business forward.

Why This Matters

Hospitality businesses don’t need louder marketing.
They need clear thinking.

Hospitality Navigator brings that clarity by:

  • diagnosing root challenges

  • recommending smart, doable next steps

  • helping you decide with confidence

  • keeping the focus on what truly matters in your business

Let’s Connect

If you’re ready for clarity over chaos, direction over distraction, and decisions over guesswork, I’d love to talk.

Explore the Hospitality Reset → (link to your offer)
Schedule a discovery call → (link to discovery page)

Contact

Jess Olivito @ Hospitality Navigator
Olivo Management Group, LLC
303 E. Prospect Ave, Ottawa, IL 61350
jess@olivitomanagementgroup.com
(312) 731-8970

How I Got Here

I didn’t set out to become a hospitality navigator — I became one by paying attention.

In 2013, I launched Dream Team Consulting, working with small businesses that needed clarity around people, operations, and growth. Over time, my work naturally gravitated toward hospitality — an industry I came to know deeply, not just from the outside, but from lived experience.

From running and advising hospitality businesses to working inside complex operations, I’ve seen firsthand how quickly pressure can build in this industry. I’ve watched talented owners struggle not because they lacked effort or vision, but because the systems around them stopped making sense — the numbers didn’t line up, the team felt misaligned, or growth created more chaos instead of relief.

I learned early that most hospitality challenges don’t start with marketing. They start with unclear information, incomplete systems, and difficult decisions being delayed.

Over the years, I leaned into the work I was naturally good at:
seeing patterns, asking the right questions, translating financial data into plain language, and helping leaders connect people, pricing, and performance into a coherent plan.

Eventually, that work earned a name.

Hospitality Navigator exists because hospitality leaders don’t need more noise — they need a steady, experienced guide who can help them understand what’s really happening inside their business and decide what to do next.

This work is the result of experience, curiosity, mistakes, resilience, and a deep respect for the people who choose to build businesses in one of the most demanding industries there is.