Careers

Are you legendary enough?

Our Company

What do an electrical engineer, a Big 4 consultant, an operations guru, a loan processor, a poker pro, and entrepreneurs have in common? Not much, other than where they work now. Our variety of experiences and skills help make Legendary Capital what it is. We don’t all think alike, but we appreciate each other’s expertise and we share a passion for taking care of our investors’ capital. When you put us all together, you have a team that is setting big goals and forging a path to achieve them.

Our Culture

Legendary Capital is in the financial industry, but our culture is far from typical. No three-piece suits or rigid office environments here – we keep it casual and flexible. We embrace our Fargo, North Dakota heritage and the “work hard-play hard” mentality of the Midwest. (We have shuffleboard, beer, and short summer Fridays.)

To be successful at Legendary Capital, you simply have to make an impact. We empower our team members to make decisions and get stuff done. We employ a unique range of skillsets and personalities, but we all share one defining trait: To do right by our investors.

If this sounds like a fit for you, apply for an open position or send us your resume. We are rapidly growing and always interested in adding another legendary mind!

Open Positions

Corporate and Local Market Sales Ambassador

Chicago, IL

The Role

We are seeking a dynamic, high-energy Sales Ambassador to drive local market share and corporate partnerships in the Chicago, IL market. This hybrid role combines grassroots canvassing with relationship-building to promote discounted hotel stays, group bookings, and our Referral Partner Program. The ideal candidate thrives in face-to-face interactions, is fearless in cold outreach, and is passionate about hospitality sales.

Base Pay: Hourly rate for canvassing OR annual salary range of $75,000–$100,000, depending on experience. Commission and performance bonuses based on revenue and partner activation. Health, dental, vision insurance, paid time off, and career growth opportunities.

Duties and Responsibilities

Duties and Responsibilities include, but are not limited to:

  • Chicago Area – Territory Canvassing: Visit businesses within a 2-mile radius for each of our properties to pitch our Mini Locally Negotiated Rate (MLNR) program and Referral Partner Program.
  • Corporate Sales: Prospect and build relationships with local companies to promote corporate lodging programs and group bookings.
  • Negotiation & Proposals: Assist in negotiating corporate rates and preparing proposals.
  • Outbound Communication: Conduct calls, emails, and client visits to generate leads and maintain relationships.
  • Rideshare Recruitment: Recruit Uber/Lyft drivers as Referral Agents to earn commissions for guest referrals.
  • Account Activation: Follow up with new partners to ensure onboarding and first booking.
  • CRM Management: Maintain accurate client records and track progress against KPIs.
  • Support Sales Manager: Assist with group booking coordination and contract administration.

Required Skills and Experience

  • Education: High school diploma required; associate or bachelor’s degree in business or marketing preferred.
  • Experience: 1–2 years in sales, customer service, or hospitality preferred; experience in canvassing or gig-economy work is a plus.
  • Skills: Excellent communication, strong organizational abilities, ability to work independently, proficiency in Microsoft Office and CRM tools.
  • Personality: Fearless, high-energy, and thick-skinned; comfortable with cold outreach and closing deals.
  • Other Requirements: Valid driver’s license for client visits.
  • Activate 20 new partners (businesses or drivers) who book at least one room within the first 60 days.
  • Meet or exceed monthly activity and revenue goals.

Apply Today

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