Top 71 Inside sales rep Jobs in Summerland Key Fl

Director of Sales (Remote)
Michael & Associates, Attorneys at Law —Florida
- $150,000 - $200,000 a year
- Full-time
- No degree
- In-person
- Senior level
Quick Apply
Business Development Sales Representative (SDA092826)
SelectQuote —Florida
- $50,000 - $80,000 a year
- Overtime
- Remote
- 1 year
- Entry level
- Paid training
- Health insurance
3d
Remote Medicare Sales Agent - Independent Contractor (1099)
MyPlanAdvocate —Florida
- $65,000 - $85,000 a year
- Contract
- Remote
- Mid-level
Wireless Zone Business Account Manager Full Time
JH Cellular —Marathon, FL
- $45,000 - $125,000 a year
- Weekends as needed
- Hybrid work
- Mid-level
- Business development
- Driver's License
- Paid training
- Health insurance
Quick Apply
Account Executive for Fast-Growing B2B SaaS Company (High Ticket Sales)
Project Blue —United States
- $6,000 - $12,000 a month
- Full-time
- Remote
- Sales
- Mid-level
- US work authorization
- Paid time off
- Flexible schedule
Quick Apply
Remote Medicare Sales Agent
Slate Professional Resources, Inc. —United States
- $21 an hour
- Overtime
- Remote
- Mid-level
- Communication skills
- Health insurance
- Dental insurance
Quick Apply
Remote Licensed Life + Health Insurance Sales Agent | Will train & Mentor | Work from Home
Sphinx Life Solutions —United States
- $80,000 - $180,000 a year
- Choose your own hours
- Remote
- Background check
- Business development
- Computer skills
- Health insurance
- Dental insurance
Quick Apply
B2B IT Services and Products Sales Representatives
PCC-IT International —United States
- Up to $500,000 a year
- Contract
- Remote
- Background check
- Hospitality
- Marketing
Quick Apply
Manager of Technical Sales Specialists - Cell and Gene Therapy - Remote, Northeast
Sartorius —United States
- $140,000 - $180,000 a year
- Full-time
- Remote
- Up to 50% travel
- Product management
- Travel
- Health savings account
- AD&D insurance
8d
Remote Bilingual Insurance Sales Person
Allstate Luis Mangandi Agency —United States
- $65,000 - $120,000 a year
- Full-time
- Remote
- Spanish
- English
- Mid-level
- Paid time off
- Work from home
Quick Apply
7d
Senior Strategic Account Executive
CXtec Inc. —United States
- $80,000 - $150,000 a year
- Remote
- Background check
- Pass drug screening
- Business development
- Paid holidays
- Disability insurance
Quick Apply

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Business Development Sales Representative (SDA092826)
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Outbound dialing sales prospects to generate interest in SelectQuote's products – upwards of 800 calls daily. Paid training - We will give you all the tools you…
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Director of Sales (Remote)

Michael & Associates, Attorneys at Law -
Florida

Quick Apply

Job Details

Full-time
$150,000 - $200,000 a year

Qualifications

Achieving large sales
Deal closing
Client rapport building
Sales training
Sales performance monitoring (sales process improvement strategies)
Sales coaching
Relationship selling
Role-playing (training delivery method)
Sales leadership
Closing sales leads
Sales follow-up
Consultative selling
Client interaction via phone calls

Full Job Description

About Michael & Associates

At Michael & Associates, we are guided by an ambitious vision: to become the premier nationwide brand in criminal defense.

While the criminal defense sector continues to depend on outdated tools like fax machines and filing cabinets, we are changing the landscape entirely.

By combining disciplined execution, innovative sales and marketing strategies, intelligent AI integration, and a steadfast dedication to outstanding client experiences, we are transforming a local service into a nationally recognized leader.

Our achievements speak volumes — we have quickly grown into one of the largest firms in Texas and recently expanded our presence to California and Tennessee.

We are now looking for a dynamic Director of Sales to join us and drive the next stage of our exciting growth.

The Role

You won’t be practicing law yourself — instead, you will be leading and supporting those who do.

Our sales attorneys are the frontline champions — the very first point of contact for potential clients during some of their most challenging times. They listen attentively, provide clear guidance, build trust, and help clients navigate the process. They already excel at their roles. Your goal? To help them become truly exceptional.

This is a unique and thrilling opportunity as our first dedicated sales leadership hire. With our rapid growth, our team of sales attorneys needs a full-time coach — not merely a part-time manager. You will lead efforts to enhance conversion rates and establish a coaching framework that elevates good representatives to top performers.

If you haven’t managed attorneys before, that’s perfectly fine — this aspect makes the role even more distinctive and rewarding. You will bring strong sales leadership and structure to a team of knowledgeable, competitive professionals who understand the law deeply but may be new to sales. Your ability to earn their respect through your expertise and leadership — beyond just your credentials — will be what truly sets you apart.

What You'll Own

Team Performance. This is your key metric. Every action you take — whether it’s a coaching session, a call review, or a one-on-one meeting — is focused on enhancing the team’s conversion efficiency.

Coaching Cadence. You will implement a structured coaching program customized to each representative’s experience level. Top performers remain sharp and motivated, mid-level performers progress to the next stage, and new or struggling reps receive intensive support, including real-time whisper coaching during calls.

Top Performer Retention. Your best team members should feel challenged, appreciated, and eager to stay. If they are leaving, it indicates a problem that needs to be addressed.

Redeploying Underperformers. Provide everyone with a fair opportunity and strong coaching, but when it becomes clear that someone cannot improve, it’s time to move on without excuses.

Requirements

Who You Are

Master of High-Volume, Consultative Sales. You haven't just taken orders—you've closed high-value deals by truly connecting with clients over the phone. Your sales approach is about listening intently, educating thoughtfully, and guiding prospects through major decisions with confidence. Having led hundreds of successful sales calls, you know exactly what top-tier performance looks like. If your experience leans more toward transactional, low-touch, or primarily in-person sales, this role might not be your perfect match.

A Coaching Dynamo. You thrive on call reviews, role plays, and one-on-one coaching. Sales attorneys eagerly anticipate your sessions because you don’t just instruct—you demonstrate, drill, and follow up relentlessly. If big-picture strategy excites you more than hands-on, day-to-day coaching, this may not be the right fit.

Unwavering Commitment to Excellence. Mediocrity isn’t in your vocabulary—for yourself or your team. You confront complacency head-on and challenge high performers to reach even greater heights. If you shy away from tough conversations or tolerate underperformance for the sake of peace, this role probably isn’t for you.

The Buck Stops With You. You’re a leader who owns the outcomes, consistently pushing goals beyond expectations. When faced with setbacks, you adapt and take responsibility rather than making excuses. If you're prone to sandbagging forecasts, griping about targets, or “managing up,” this environment won’t suit your style.

A Natural Energy Booster. Intake calls can get repetitive, but your enthusiasm keeps the team motivated and morale sky-high. You celebrate every win and turn routine work into an exciting, dynamic experience. If you tend to be low-energy or believe motivation is solely the employee’s responsibility, this won’t be the right fit.

Results-Obsessed. You live by results, meticulously tracking performance and linking every coaching effort directly to business outcomes. You’re always setting the bar higher. If you prefer to sandbag or resist escalating goals, this won’t be the place for you.

Decisive with Tough Personnel Decisions. You give underperformers a genuine chance—with honest coaching, clear feedback, and meaningful support. But when it’s clear someone isn’t the right fit, you take swift, confident action. If you’ve never had to let someone go or avoid those difficult conversations, this role may not suit you.

AI Trailblazer. You embrace AI fully, pushing its boundaries in your daily work. You’ve discovered innovative use cases and are excited to share how AI boosts your performance. If you think simply using ChatGPT means you’ve harnessed AI’s power, this won’t be the best match.

This Role Is NOT

A player-coach position. You won’t be handling intake calls yourself; your focus is on elevating the team, not being the top rep.
A strategy-only role. Forget about building decks or spending hours in planning meetings—this is hands-on, everyday coaching in the thick of the action.
A traditional legal management role. No law degree required, and legally, you won’t be reviewing legal work—your impact is all about driving sales performance. We’re looking for a proven sales team booster.
A maintenance job. We’re growing rapidly across multiple states, and what works today won’t necessarily work tomorrow. You need to thrive in a fast-evolving environment.

What Success Looks Like — Year 1

The team’s conversion rates have significantly improved since you came on board.
You’ve retained all top performers—your best talent is motivated to stay and advance.
You’ve established a coaching rhythm that reps genuinely value, not just tolerate.
Performance management is crystal clear: top performers are celebrated, and underperformers are either coached up or transitioned out.
You’ve created a scalable, repeatable system that supports growth as we add more reps and expand into new states.

IMPORTANT:

If you have previously applied for the Sales Director position, please refrain from submitting multiple applications, even if the job is listed in several states. A single application is enough and will be reviewed for all relevant locations.

When applying, kindly submit your application only to the job posting corresponding to the state where you are currently living.

Benefits

$150,000 - $225,000 total compensation package

Pay: $150,000.00 - $200,000.00 per year

Work Location: In person

Quick Apply

Refine Your Search

inside sales rep jobs in summerland key fl

Director of Sales (Remote)

Business Development Sales Representative (SDA092826)

Remote Medicare Sales Agent - Independent Contractor (1099)

Wireless Zone Business Account Manager Full Time

Account Executive for Fast-Growing B2B SaaS Company (High Ticket Sales)

Remote Medicare Sales Agent

Remote Licensed Life + Health Insurance Sales Agent | Will train & Mentor | Work from Home

B2B IT Services and Products Sales Representatives

Manager of Technical Sales Specialists - Cell and Gene Therapy - Remote, Northeast

Remote Bilingual Insurance Sales Person

Senior Strategic Account Executive

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