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  • Home
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Meet Our Sales Experts

Jessica Caldwell

Jessica Caldwell

Jessica Caldwell

"Sales motivation is not about hype or volume. It is about clarity, ownership, and momentum. Know exactly what you are responsible for, why it matters, and how today connects to tomorrow."

Tom Tsilionis

Jessica Caldwell

Jessica Caldwell

"Closing is not a personality trait. It is a discipline. Deals do not close because someone is charismatic or aggressive; they close because the salesperson earned the right to ask for a decision."

Jimmy Garaffalo

Jessica Caldwell

Jimmy Garaffalo

"Great sales conversations are built on balance, not bravado. When you slow down to hear what is actually being said, objections turn into information and silence becomes signal. "

Jennifer Vahn

Jessica Caldwell

Jimmy Garaffalo

"Sales leadership is not about control or charisma. It is about setting standards, creating clarity, and removing friction so your team can perform at their best with little motivation and guidance."

5/19/2025

Leadership Summit 2025

All day

Lake Buena Vista, FL

Event Details

5/19/2025

Leadership Summit 2025

The EntreLeadership Summit 2026 is a four-day leadership event geared toward business owners, executives, and entrepreneurs, focused on shar...

Event Details

All day

Lake Buena Vista, FL

9/13/2026

Sales & Marketing Insights

Sep 13, 10:00 AM

-

Sep 13, 12:00 PM

Leows Hotel, Atlanta

Event Details

9/13/2026

Sales & Marketing Insights

Jessica Caldwell will be attending the Student Sales & Marketing Conference in Atlanta and will be available for short, one-on-one consultat...

Event Details

Sep 13, 10:00 AM

-

Sep 13, 12:00 PM

Leows Hotel, Atlanta

Advance Your Sales Performance

A leadership conference hosted by The Sales Lounge should sound sharp, human, and a little dangerous—in the good way. Leadership isn’t about laminated badges and buzzwords; it’s about influence under pressure. Here are some names that lean into that truth.

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Join & Boost Your Sales

11/28/2020

Sales Boost Night

7pm

-

10pm

Estuary Park, 7-10pm

Event Details

11/28/2020

Sales Boost Night

Maximize your sales potential. Join us for expert strategies and networking at Estuary Park.

7pm

-

10pm

Estuary Park, 7-10pm

9/13/2026

Student Sales Conference

10:00 AM

-

12:00 PM

Leows Hotel, Atlanta, Georgia

Event Details

9/13/2026

Student Sales Conference

Jessica Caldwell will be attending the Student Sales & Marketing Conference in Atlanta and will be available for short, one-on-one consultat...

Event Details

10:00 AM

-

12:00 PM

Leows Hotel, Atlanta, Georgia

9/17/2026

IN26: Build Your Future

1:00 PM

-

4:00 PM

Boston, MA

Event Details

9/17/2026

IN26: Build Your Future

Build your future at INBOUND 2026 (HubSpot)—where marketing, sales, AI, and leadership collide in one gloriously nerdy ecosystem. IN26 is a ...

Event Details

1:00 PM

-

4:00 PM

Boston, MA

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