Remote Territory Sales Pro — Education Tours (Chicago)

Pursuit; Chicago (IL); On-site; USD 110,000 - 140,000; Full time

Benefits offered by this job

OTE $110K+ year-one including base,unc

Car allowance + mileage reimbursement

Expenses account for travel and client

15 days PTO + paid holidays

401(k) with company match

Job summary

Pursuit in Chicago is seeking a driven sales professional to join a family-owned leader in customized educational tours. You will own the City of Chicago territory, build relationships with educators, and guide schools from inquiry through travel planning and execution.

This remote-first role offers a base salary with uncapped commissions, generous allowances, and a culture focused on growth, impact, and client partnerships.

Qualifications

• 2+ years of successful new-business sales experience.
• Hunter mentality and the initiative to build a territory.
• Experience with consultative, relationship-based selling.
• Strong communication skills, empathy, and the ability to connect with educators.
• Understanding that success requires more than high-volume cold calling—it comes from earning trust, understanding client needs, and developing lasting partnerships.

Responsibilities

• Own and grow the City of Chicago territory.
• Work remotely when not meeting with clients.
• Manage the full sales cycle from prospecting to closing and partnerships.
• Build trusted relationships with educators and school admins.
• Understand each school's needs and tailor travel experiences.
• Stay active in the field through face-to-face meetings and community networking.

Skills

New-business sales

Hunter mentality

Consultative selling

Relationship building

Communication skills

Educator engagement

Job description

Pursuit in Chicago is seeking a driven sales professional to join a family-owned leader in customized educational tours. You will own the City of Chicago territory, build relationships with educators, and guide schools from inquiry through travel planning and execution.

This remote-first role offers a base salary with uncapped commissions, generous allowances, and a culture focused on growth, impact, and client partnerships.