Fifty & Five
Orlando, FL · Fractional CMO

I have led marketing and social strategy for 222+ brands across 5 continents since founding Fifty & Five in 2008. I take on a small number of Orlando-area owner-operators as fractional CMO clients — senior strategy on call, without adding another full-time hire.

Track record

Eighteen years, one operator, running from Orlando.

2007

Corporate Marketing Manager, Southern Wine & Spirits. Built the company’s first marketing department. 15% average lift in case sales. Zero prior wine industry experience.

2008

Founded Fifty & Five. One of only two American agencies (alongside VaynerMedia) built from scratch as social-first, no pivot from PR or advertising.

2016

Gruppo Mezzacorona retainer begins. Ten years, 5+ brands in portfolio, roughly 1M followers added.

2020

Kendall-Jackson partnership begins. Multi-year, still active.

2026

222+ brands managed across 5 continents. Senior + AI operating model in market. Serves on the SoDo Main Street Board in Orlando.

The seat

What working with me looks like.

Every month

a 60-90 minute strategy session. Not a status meeting.

Every month

a written Marketing Command Brief: what moved, what I'm flagging, what's next.

Every month

one prioritized strategic recommendation, scoped and ready to execute.

On call

direct text access to me. Not a support queue.

Not included

Hands-on execution: content production, ad management, website builds. That is real work, priced and scoped separately through Fifty & Five, so the seat stays strategic advice.

Why Orlando

I am here, not remote.

Fifty & Five has run from Orlando since 2008. If you are an Orlando-area owner-operator, you get an operator who has run this playbook in this market for 18 years, backed by the same team that runs marketing for Microsoft, Kendall-Jackson, and Enterprise Holdings. Not a coach parachuting in from out of state.

Frequently asked

Straight answers about the seat.

What does a fractional CMO in Orlando cost?

My seats run $4,000-$6,500 per month, scoped to the business and how much oversight it needs, on a month-to-month basis with no long-term contract. That is roughly a third of what a full-time CMO costs before benefits and equity.

What is Lucas Vandenberg's background?

I built the first marketing department at Southern Wine & Spirits starting in 2007, then founded Fifty & Five in 2008. Since then I have led marketing and social strategy for 222+ brands across 5 continents, including Microsoft, Kendall-Jackson, Mezzacorona, Enterprise Holdings, and Tupperware, from Orlando, Florida.

Does a fractional CMO replace my in-house marketing person?

No. I set strategy and direction; your existing marketing person or agency still executes. Most clients keep their in-house hire and use the seat to give them a plan and a senior sounding board instead of guessing alone.

What size company is a good fit?

Owner-operated companies doing $1M to $20M in revenue, in or around Orlando or Central Florida. Large enough that marketing run on instinct is costing real money, not yet large enough to justify a full in-house executive.

Is there a contract?

No lock-in. Month to month, 30-day notice. The work has to earn the renewal every single month, that is the guarantee.

What does a fractional CMO do?

A fractional CMO sets marketing strategy, budget, and channel priorities on a part-time or advisory basis, without becoming a full-time hire. I run a monthly strategy session, deliver a written brief on what moved and what is next, hand over one prioritized recommendation, and stay on call by text in between.

Why hire a fractional CMO in Orlando instead of a national firm?

A national fractional CMO firm assigns you a consultant you may never meet in person and who has not run this specific market. I am based in Orlando, have run Fifty & Five from here since 2008, and take the seat myself, not a firm placement.

A 30-minute call. Your numbers, your bottleneck, and whether it makes sense. No deck, no pressure.

LIVE
MicrosoftSAPKendall-JacksonEnterprise Rent-A-CarNational Car RentalAlamoBlaze PizzaDiscovery ChannelAmerican Airlines CenterToys R UsResorts WorldAxe / UnileverNETGEAR / ArloLinksysTupperwareWarner Bros.PenfoldsMolina HealthcareThe Irvine CompanyAutoNationBain & CompanyWolfgang's SteakhouseHasbroMicrosoftSAPKendall-JacksonEnterprise Rent-A-CarNational Car RentalAlamoBlaze PizzaDiscovery ChannelAmerican Airlines CenterToys R UsResorts WorldAxe / UnileverNETGEAR / ArloLinksysTupperwareWarner Bros.PenfoldsMolina HealthcareThe Irvine CompanyAutoNationBain & CompanyWolfgang's SteakhouseHasbro