Outside Sales Team Lead

Tailor On Tap; Tysons (VA); On-site; USD 60,000 - 80,000; Full time

Job summary

Tailor On Tap is seeking an experienced Outside Sales Team Lead to build and lead a high-performing sales unit in Tysons Corner, VA. In a player-coach role, you’ll manage your own book of business while developing a team of stylists, recruiting talent, and collaborating with leadership to drive new business and improve sales processes.

You’ll guide coaching, prospecting, consultative selling, and relationship-building with executives and professionals, enabling repeat business and referrals.

Qualifications

• Proven track record in relationship-driven sales.
• Built a meaningful book of business.
• Able to generate leads and appointments.
• Expertise in consultative selling.
• Experience coaching and developing salespeople.
• Strong CRM and pipeline management knowledge.
• Experience recruiting and onboarding new hires.
• Comfortable selling to executives and high-income professionals.

Responsibilities

• Lead from the front and manage your own book of business.
• Coach and develop the sales team, including regular 1:1s and training.
• Recruit, onboard, and train new stylists.
• Teach our sales process, products, fabrics, pricing, measurements and consultations.
• Drive prospecting, follow-up, referrals and business development.
• Review pipelines and sales activity to optimize performance.
• Establish clear expectations and hold the team accountable.

Skills

Relationship-driven sales

Book of business

Lead generation

Consultative selling

Coaching & development

CRM & pipeline mgmt

Recruiting

Executive selling

Tools

CRM

Job description

Outside Sales Team Lead, Custom Clothing

Tailor On Tap | Tysons Corner, VA | Full-Time | On-Site

Build Your Book. Build Your Team. Participate in the Success of Both.

Tailor On Tap is looking for an experienced, entrepreneurial Sales Team Lead to help us build the next stage of our sales organization. This is a player-coach role. You’ll maintain your own book of business while coaching and developing a team of sales professionals. You’ll work directly with company leadership to drive new business, strengthen sales processes, develop our existing team, and help recruit and train future stylists.

What You’ll Do

• Lead From the Front
• Build and maintain your own book of business
• Prospect and generate new appointments
• Develop referral and networking relationships
• Build relationships with executives, entrepreneurs, attorneys, professionals, and organizations
• Conduct custom clothing consultations
• Generate repeat and referral business
• Demonstrate the sales behaviors you expect from your team

Coach & Develop the Sales Team

• Conduct regular sales coaching and one-on-ones
• Coach prospecting, follow-up, referrals, and business development
• Review pipelines and sales activity
• Help stylists build their own books of business
• Improve consultation and closing skills
• Role-play and train sales scenarios
• Establish expectations and hold the team accountable
• Identify performance gaps and create plans for improvement

Recruit & Build the Team

• Participate in recruiting and interviewing future stylists
• Help onboard and train new hires
• Teach our sales process, products, fabrics, pricing, measurements, and consultations
• Conduct mock consultations and role-playing

What We’re Building

We want to create a sales organization where stylists actively generate business rather than simply wait for appointments.

You’ll help build a culture centered around:

• Prospecting and networking
• Client development and retention
• CRM and pipeline management
• Repeat business
• Partnerships and events

Compensation & Earning Potential:

We believe sales leaders should participate financially in the success they create.

This position includes:

• Uncapped personal sales commission, with rates reaching up to 20% of personal sales
• Additional team-based compensation tied to the performance of the salespeople you develop
• Additional performance incentives as the company and sales organization grow
• No cap on total earning potential
• Long term vesting opportunity

The better you sell, the better your team performs, and the more the organization grows — the greater your earning potential becomes. The base salary for the role is $60K–$80k with $90k- $100K+ realistic earning potential.

Who We’re Looking For

You may be a strong fit if you:

• Have a proven track record in relationship-driven sales
• Have built a meaningful book of business
• Generate your own leads and appointments
• Are comfortable prospecting and networking
• Understand consultative selling
• Have coached or trained other salespeople
• Enjoy developing people and holding them accountable
• Understand CRM and pipeline management
• Are competitive, entrepreneurial, and goal-oriented
• Are comfortable selling to executives and high-income professionals
• Want compensation tied directly to the value you create
• Most importantly, you still like to sell.

Custom clothing or luxury menswear experience is highly desirable, but it isn’t required.

We’re also interested in strong candidates from:

• Luxury goods
• Professional services
• Outside B2B sales
• High-end hospitality
• Other relationship-driven sales organizations

Custom clothing can be taught. The ability to build relationships, generate business, sell, lead, and develop other salespeople is much harder to teach.

Where This Can Go:

This role is designed for someone who wants more than their next sales job.

As Tailor On Tap grows, the Sales Team Lead can grow into broader sales leadership with responsibility for recruiting, training, developing, and leading an expanding sales organization.

Whether you’re a top-performing salesperson ready to lead or an experienced sales leader eager to sell again, this role lets you build your book and team while sharing financially in the success you create.