Regional Sales Executive

Valet Living; Chicago (IL); Hybrid; USD 65,000 - 80,000; Full time

Benefits offered by this job

Health benefits

401k with company match

Tuition reimbursement

Job summary

Valet Living, LLC is seeking a results-driven sales professional to own a designated territory and drive new business for resident-facing amenities in multifamily communities. You’ll prospect, present, and close opportunities with senior leaders and asset managers while managing a high-velocity pipeline.

The role offers blended field and remote work with up to 70% travel within your territory, a strong commission structure, and ongoing professional development.

Qualifications

• Minimum of five (5) years of B2B outside consultative sales experience.
• Proven track record of closing new business.
• Valid Driver’s License and willingness to travel within territory.

Responsibilities

• Own and Grow a Territory by executing a go-to-market strategy.
• Develop New Business by engaging managers, asset owners, and owners to meet targets.
• Build and Scale Pipeline through outbound prospecting and meetings.
• Manage Complex Sales Cycles with multi-stakeholder processes.
• Position Value & Differentiate Valuation of Valet Living’s offerings.

Skills

New Business Development

Sales Prospecting

Client Management

Tools

Salesforce

Job description

Own the Territory. Win New Business. Build a Career That Grows With You.

At Valet Living, you’re not just selling a service, you’re delivering solutions that transform communities, drive property value, and elevate the resident experience. Backed by industry-leading technology, a culture grounded in growth and servant leadership, and rewards that recognize overachievement, this is a platform built for top producers.

Reporting to the Regional Sales Manager, you’ll play a critical role in driving growth by owning a designated territory and promoting Valet Living’s resident-facing amenities to multifamily communities. You’ll generate, develop, and close new opportunities while expanding our footprint across this key segment of the real estate market.

This role is focused exclusively on new business development and requires selling to senior leaders, asset managers, and owners while building strong relationships at the regional and community level. We’re looking for a motivated, quick-learning sales professional who thrives in a results-driven, high-performance environment and is driven to succeed.

Compensation & Work Environment Details

On-Target Earnings (OTE): $117,000 - $144,000

Salary Range: $65,000 - $80,000

Monthly Commission: Uncapped

Ramp Up Guarantee: Monthly guarantee during ramp-up period

Auto Allowance & Reimbursement: Bi-weekly fixed contribution + monthly variable mileage reimbursement

Work Environment: Blended field-based & remote role with up to 70% travel within your territory

What You’ll Do

• Own and Grow a Territory: Execute a comprehensive go-to-market strategy that drives sustained revenue growth and increases market penetration across assigned markets.
• Develop New Business: Identify, pursue, and close new business opportunities by engaging community managers, regional managers, property owners, asset managers, and management groups to consistently meet and exceed monthly closing targets.
• Build and Scale Pipeline: Rapidly develop a robust pipeline through outbound prospecting, industry networking, phone outreach, in-person and virtual meetings, and other lead generation strategies.
• Manage Complex Sales Cycles: Lead multi-stakeholder, consultative sales processes, navigating decision-making structures and tailoring solutions to client needs from initial engagement through contract execution.
• Position Value & Differentiate Solutions: Serve as a trusted subject-matter expert by clearly articulating Valet Living’s value proposition, delivering compelling presentations, and differentiating solutions in a dynamic market.
• Support Client Transitions: Partner closely with Account Management and Operations teams to ensure smooth handoffs, clear expectations, and successful service launches for new clients.
• Maintain CRM Discipline: Ensure accurate documentation, forecasting, and pipeline visibility through consistent use of Salesforce.
• Invest in Development: Engage in ongoing professional development, coaching, and skill-building while staying current on industry trends and best practices.

We’re Looking For

• New Business Focus: You bring a consultative, growth-oriented mindset with a proven ability to originate and close new business in a results-driven, high-performance environment.
• Industry Experience Preferred: Previous experience selling in the multifamily industry is a plus but not required.
• Proven Sales Performance: Minimum of five (5) years of B2B outside consultative sales experience, with a strong track record of closing new business, navigating long sales cycles, and succeeding in a split compensation structure.
• Self-Motivated & Results-Driven: You don’t need hand-holding - you thrive on autonomy, accountability, and consistently delivering strong results.
• Consultative Sales Expertise: Ability to leverage persuasion, negotiation, and influence to engage economic buyers and decision-makers at all levels, including senior leaders, asset managers, and owners.
• Sales Methodologies: Experience with sales methodologies such as Miller Heiman/Korn Ferry Sell, Challenger, Sandler, MEDDPICC, SPIN, or Value Selling.
• Tech-Savvy & Organized: Salesforce experience preferred; strong time management, organization, and planning skills required to manage a high-velocity pipeline.
• Commitment to Growth: A mindset of continuous learning, professional development, and active contribution to company culture.
• Valid Driver’s License: This role requires frequent travel within your designated market.

Why You’ll Love Working With Us

At Valet Living, we don’t just provide essential services; we build careers, create opportunities, and cultivate a culture of excellence. As part of our team, you’ll experience a workplace where leadership is about service, growth is the norm, and every detail matters.

Robust Training Program

• 4-week structured onboarding program to set you up for success
• Hands-on mentorship and ongoing support

Comprehensive Benefits

• Health Benefits: Medical, dental, and vision coverage for you & your family, plus HSA with employer contributions and Flexible Spending Accounts
• Flexible Time Off: No preset accruals - manage your time and work-life balance your way, plus 10 company-paid holidays.
• Financial Security: 401k with company match, life and disability insurance, AD&D, and business travel coverage
• Professional Development: Tuition reimbursement up to $5,250 per year and access to our online education center
• Additional Perks: Referral bonuses, pet insurance, associate assistance programs, discount programs, rewards, recognition, and free access to Torch Fitness virtual programs

The final compensation offered will be determined based on various factors, including the candidate's location, level of experience, and skill set. As such, it may fall outside the range listed above. OTE varies based on performance.

The application window is anticipated to close 60 days from the date the job is posted.

Valet Living is an Equal Opportunity Employer that values the strength diversity brings to the workplace. We recruit, employ, train, compensate, and promote without regard to race, religion, creed, color, national origin, age, gender, sexual orientation, gender identity, marital status, disability, veteran status, or any other basis protected by applicable federal, state or local law.