Fractional sales leader in Miami for founder led B2B companies

By Kerry Sullivan, fractional Head of Sales · Updated October 12, 2026

I’m Kerry Sullivan, a fractional Head of Sales based in Miami Beach. I work with B2B founders who are still running every deal themselves and want a sales process, a CRM they trust and a ramping rep, without hiring a full time VP of Sales yet.

Who I work with in Miami and South Florida

Miami’s startup scene has grown a lot, and many of the founders here sell by phone and video to customers all over the country. That suits a fractional model well. I work with companies that:

sell to businesses, not consumers, with a sales conversation in the middle of the buying process;
have paying customers and a founder who is still on most calls;
have between zero and ten reps;
use HubSpot, GoHighLevel or Pipedrive, or are about to pick a CRM.

Most of the work happens on video, so you do not have to be in Miami. But if you are in Miami Beach, Brickell, Wynwood, Coral Gables, Fort Lauderdale or Boca Raton, we can meet in person for the kickoff and for key working sessions.

What working together looks like

My main program is called The Founder Handoff. It runs 90 days and has a simple goal: sales stops depending on the founder.

Audit. I sit in on your calls, review the pipeline and talk to the team. You get a written list of the top problems slowing deals down. If the audit does not find real problems, you get your money back.
Playbook. We write down who you sell to, how discovery works, the objections you hear and how to answer them, and the steps every deal goes through.
CRM. I guide your team to optimize your CRM: pipeline stages, required fields, dashboards and follow up automations, so the pipeline reflects reality.
Hiring. If you need a rep, we build the scorecard and interview process, and I help you run it, so your first or next hire starts on a real ramp plan.
Coaching. Weekly call reviews and deal coaching, so the rep improves and the founder can step back on a planned date.

Your time commitment is about 2 hours a week. Pricing is public: $7,500 a month for months 1 to 3 at about 2 days a week, then $4,500 a month for ongoing fractional leadership or $1,500 a month for Rep Coaching. See the cost guide for how that compares to market ranges.

Why fractional instead of a full time hire

A full time VP of Sales is a big commitment for an early company: salary, equity, benefits and months of hiring. It also tends to fail when there is no written process for them to scale. Fractional leadership lets you build the foundation first at a fraction of the commitment. When you are ready for a full time leader later, they step into a working system.

My background

I have built sales processes and coached reps at Empower and LeadEvo, and I was Sales Director at SuperAgent AI. My coaching style is question based and low pressure: reps learn to understand the buyer and find the real problem, so the right deals close without anyone being pushy.

Before sales I was a professional triathlete, and I raced seven world championships as an amateur. Endurance sport is a good teacher for sales management. You win with a simple plan, daily habits, honest feedback and steady improvement, not with one heroic week.

Questions to ask any fractional sales leader

Whether you hire me or someone else, a few questions will tell you a lot. Ask how many days a week you are actually buying. Ask what will exist at the end of 90 days, as a written list. Ask whether they coach reps directly or only advise the founder, and ask to see an example of a playbook or ramp plan with client details removed. Ask what they guarantee and what they do not. Anyone who promises a revenue number without knowing your product and market is guessing.

Remote clients outside Florida

Most of my clients do not need me in the room. I work across US time zones on video, with recorded call reviews and a shared CRM. Being in Miami mainly means Eastern time hours, which works well for East Coast teams and is easy for Central and West Coast teams too.

How to start

The first step is a free 30 minute Sales Teardown on video. You walk me through how you sell today and I ask questions. Afterward I email you the top 3 things slowing your sales down. If I am not the right fit, I will say so and point you somewhere better. I take on 2 Founder Handoff clients at a time.

If you are not ready for a call, the free Founder Sales Handoff Checklist lists 21 things to have in place before your first sales hire.

Related guides

Want help handing off sales?

Book a free 30 minute Sales Teardown. You walk me through how you sell today, and I email you the top 3 things slowing your sales down.

Book your free Sales Teardown

Not ready for a call? Get the free Founder Sales Handoff Checklist: 21 things to have in place before your first sales hire.

Frequently asked questions

Do you only work with Miami companies?

No. I am based in Miami Beach and can meet South Florida clients in person, but most work is on video and I work with founders anywhere in the US.

What industries do you work with?

B2B companies that sell through a sales conversation by phone or video, such as software, services and agencies. If you are not sure, we can check on the free Teardown.

How much time does it take from the founder?

About 2 hours a week: one deal coaching session, plus interviews when you are hiring.