Field Sales Representative

Born from a partnership with a Leading Hotel of the World, Peak is already transforming the reservation experience in Palm Springs and Miami. Now, we're bringing Peak to Chicago-home to some of the country's most innovative chefs, neighborhood gems, and hospitality powerhouses-and we need the right sales leader to drive growth in this territory.

Peak allows guests to reserve and select their exact table of choice online. We're passionate about building a best-in-class reservation experience that elevates both guests and restaurants-something that aligns perfectly with Chicago's culture of hospitality.

What does it mean to be a Field Sales Representative at Peak?

You'll join a fast-paced, relationship-driven sales environment, playing a pivotal role in bringing Peak to the Chicago market. This is your opportunity to build and own a brand-new territory from the ground up-embracing a true "mayor of your neighborhoods" mentality.

You'll walk the bustling blocks of West Loop, drop into lively spots in River North, explore chef-driven concepts in Logan Square, and build relationships with the operators behind Chicago's most beloved restaurants. You'll prospect, qualify, and shepherd deals to close-helping Peak become an essential tool across the city.

If you're an ambitious, field-oriented sales professional with a passion for hospitality and technology, this role is the perfect fit.

The ideal Chicago Field Representative will...

• Be in the field visiting restaurants 5 days per week across neighborhoods like:
  
  • West Loop / Fulton Market - home to Girl & the Goat, The Publican, Au Cheval, and countless chef-led concepts
  • River North - with high-volume destinations like RPM Italian, Etta, Tanta, and Shaw's Crab House
  • Gold Coast - featuring Maple & Ash, Gibsons Bar & Steakhouse, Le Colonial, and boutique luxury dining
  • Logan Square - known for Andros Taverna, Giant, Lula Cafe, and other independent culinary leaders
  • Wicker Park & Bucktown - with staples like Big Star, The Violet Hour, and popular neighborhood hotspots
• Build credibility and relationships with Chicago's top hospitality groups, including Lettuce Entertain You, Boka Restaurant Group, Hogsalt Hospitality, One Off Hospitality, and DineAmic Hospitality
• Bring proven sales experience with consistent success in a quota-carrying role
• Understand the unique challenges and opportunities within Chicago's food and hospitality ecosystem-including seasonality, neighborhood-specific dining patterns, and the blend of independent operators and large groups
• Be comfortable using CRM tools and sales prospecting software (we use HubSpot)

• Base Salary: $65,000-$75,000
• On-Target Earnings (Year 1): $100,000-$120,000+ with uncapped commission

• Own and drive the full sales cycle in your Chicago territory, resulting in closed-won deals
• Build and maintain strong, trust-based relationships with restaurant owners, GMs, operators, and key decision-makers

• Research and identify prospective Chicago restaurants and the stakeholders behind them
• Qualify leads and schedule in-person and virtual meetings
• Build and maintain a well-organized pipeline in HubSpot
• Develop tailored lead-generation strategies for Chicago's diverse dining neighborhoods
• Meet and exceed monthly and quarterly targets for qualified meetings and opportunities

• 1+ years of experience in sales development or lead generation
• Excellent verbal and written communication skills
• Ability to work independently while collaborating with the broader Peak team
• Strong work ethic and self-motivation
• Highly organized with exceptional attention to detail
• Energized by a fast-paced, target-driven environment

• Expense account for in-field prospecting, dining, and travel
• Comprehensive medical, dental, and vision insurance
• 401(k) plan