Florida Regional Director of Sales Enablement

About Us

The company is a home improvement services company focused on residential roofing and other exterior services across the United States. Backed by Alpine Investors, a top-decile private equity fund with $4.0 billion of committed capital, the company is building a best-in-class national platform. Our company is built on our core values— servant leadership, unwavering character, a growth mindset, persistence, empowerment, pace, and fun —and guided by three pillars: being the Employer of Choice , Partner of Choice , and Contractor of Choice . We offer transformative support in operations, marketing, training, talent, finance, and technology, all while preserving the autonomy of local brands.

As the Florida Regional Director of Sales Enablement, you will deliver classroom-based sales training through the company Sales University (VSU), provide live field coaching through ride-alongs, and directly drive the performance of new and veteran sales reps across the company’s Florida markets. You will serve as the region’s tile and metal roofing expert, advise on curriculum strategy, mentor Sales Managers, and lead through influence across a multi-company, multi-market region — owning the performance outcomes of every rep who comes through the program.

Key Responsibilities

Co-Lead VSU Training Programs

• Deliver and co-lead VSU bootcamp training sessions for new sales reps at the VSU training center in Atlanta

• Teach the company’s 10-step consultative, one-call close sales process with the credibility of someone who has lived it

• Drive rep skill development through high-engagement facilitation — role play, live demonstration, and real-time feedback

Drive Florida Regional Performance

• Own post-VSU sales rep performance across all Florida markets

• Lead through influence — no direct reports, but full accountability for the output of every rep and sales manager in the region

• Identify underperforming markets, reps, or leaders early and act through targeted coaching and field support

• Track and analyze key performance indicators across the region, surface trends, and present solutions to leadership

Field Coaching & Sales Manager Mentorship

• Travel regularly into Florida markets to provide in-field coaching via ride-alongs alongside sales reps and sales managers

• Mentor and advise sales managers on coaching technique, performance management, and team development

• Lead onboarding training for new sales reps during critical onboarding and performance windows

Training Strategy & Curriculum Development

• Partner with the VP of Sales, Florida Region, and the National Sales Enablement Team to advise on curriculum design, program structure, and training strategy — all to drive revenue growth

• Use AI tools, modern LMS platforms, and field expertise to build, refine, and maintain high-quality training materials

• Identify performance trends and coaching gaps from post-VSU data and bring actionable recommendations to leadership

• Collaborate with fellow Regional Directors and Sales Directors to ensure consistency and continuous improvement across all training markets

Key Outcomes

• Post-VSU sales rep NSLI and Close Rate % performance across all Florida markets, tracked in the first 90 days and on an ongoing basis

• Complete the full 3.5-week VSU bootcamp as a participant, then begin co-leading VSU training sessions under the guidance of senior VSU team members

• Travel to all Florida markets within the first 90 days to meet sales leaders, stakeholders, and sales teams, and build field-level context

Qualifications & Characteristics

Required

• Proven track record in 1-call-close tile, metal, and shingle residential retail roofing sales, or another in-home, one-call-close home improvement sales model — this is a hard requirement

• Deep, working command of consultative selling — fluent in the steps and why they work

• Natural facilitator who can command a classroom, coach one-on-one, and adapt in the moment

• Tech-savvy — uses AI tools, digital platforms, and technology to work smarter, and is genuinely excited to apply them to training

• Located in or willing to relocate to the Florida region — proximity to Orlando and Tampa strongly preferred

• Extreme ownership mindset — success is measured by what reps and managers do in the field, not by classroom activity

Preferred

• Prior experience in a formal training, coaching, or sales leadership capacity

• Experience building training materials, playbooks, or onboarding content

• Familiarity with LMS platforms, AI productivity tools, or sales enablement technology

• Experience working across multiple markets or company locations

What You’ll Get

• Regional ownership — a defined geography, clear accountability, and the authority to drive performance across Florida market

• A direct voice in how sales training is designed and executed across a $650M national platform

• A clear path into senior VSU leadership — this role is a pipeline into expanded strategic responsibility

• Close collaboration with the VP of Sales Enablement and national sales leadership from day one

• A culture built on accountability, craft, and continuous improvement

Compensation

• Competitive base salary with a target range of $110,000–$210,000, plus eligibility for performance-based bonuses (total on-target earnings of $190,000–$210,000)

• Equity participation may be available, depending on role scope and experience

Compensation & Benefits Disclosure

Compensation for this role may be provided as hourly pay, salary, commission, piece-rate, bonuses, incentives, or a combination of these methods, depending on the position. The “Estimate of Total Expected Annual Earnings” listed reflects our good-faith estimate of what we reasonably expect to pay for this role, based on factors such as experience, skills, candidate geographic location, state the job is located in, historical trends, and business needs. Actual earnings may vary.

Where required by law, we also provide a general description of benefits and other forms of compensation offered, which may include health insurance, retirement plans, paid time off, and other employee programs.

Estimate of total expected annual earnings

$190,000 — $210,000 USD

Benefits

Full-time employees are eligible to participate in the following benefits:

• Health, Dental, and Vision Insurance

• 401(k) with company match

• Company sponsored Life and AD&D coverage

• Paid Time Off

• Opportunities for growth and on-the-job training

Why Join Us?

• Build Something Big – Shape processes for a rapidly growing organization.

• Growth-Oriented Culture – Work in a dynamic, people-first environment.

• Make an Impact Across Regions – Partner with business leaders to drive meaningful change.

Apply Today!

The company is an equal opportunity employer and does not discriminate based on race, color, religion, sex, national origin, political affiliation, sexual orientation, marital status, disability, age, military service, or any other protected class. If you need a reasonable accommodation due to a disability, please contact Human Resources with your request and contact information. Applicant Privacy Policy