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Account Executive; Chicago

Remote / Online - Candidates ideally in
Chicago, Cook County, Illinois, 60290, USA
Listing for: Tripleseat
Remote/Work from Home position
Listed on 2026-01-12
Job specializations:
  • Sales
    Sales Development Rep/SDR, Technical Sales
Salary/Wage Range or Industry Benchmark: 100000 - 125000 USD Yearly USD 100000.00 125000.00 YEAR
Job Description & How to Apply Below
Position: Account Executive (Chicago)

Join to apply for the Account Executive (Chicago) role at Tripleseat

Tripleseat is the leading web-based event management and sales platform designed for restaurants, hotels, and unique venues. Our mission is to simplify and streamline the event planning process, allowing our clients to focus on delivering exceptional customer experiences. We pride ourselves on fostering a collaborative, innovative work environment that encourages growth and development.

As an Account Executive at Tripleseat, you will be a vital part of a dynamic team responsible for driving revenue growth within an assigned territory. This remote role involves a blend of prospecting, closing deals, delivering software demonstrations, and collaborating with internal teams to support customer success. The role demands high self-motivation, a passion for the hospitality industry, and a proven ability to meet and exceed sales targets.

You will represent Tripleseat's event management platform, offering tailored solutions to potential clients in the hospitality sector.

Location:

This position is open to candidates eligible to work in the United States, located in the Chicago area.

Travel Expectations:
Candidates are expected to maintain an in-person presence at least once per week for sales meetings and events. Travel to our Concord, MA headquarters is required for company events and training.

Core Responsibilities
  • Prospecting & Lead Generation:
    Actively seek out new business opportunities within your territory by identifying and engaging prospective customers through multiple channels, including but not limited to cold calls, emails, social media, and walk-ins. Develop key industry relationships virtually, using a mainly inside sales approach to prospecting.
  • Sales Targets:
    Achieve and surpass assigned sales quotas by independently managing outbound sales activities and opportunity building.
  • Customer Engagement:
    Conduct discovery calls, deliver software demonstrations, and tailor proposals to meet customer needs.
  • Software Demonstrations:
    Deliver in-person and virtual software demonstrations to showcase Tripleseat’s platform. Highlight how Tripleseat addresses customer pain points, provide technical expertise, and answer any questions related to product functionality and integration.
  • Territory Management:
    Maintain a robust pipeline of opportunities, aiming to keep it at least five times the annual revenue quota. Actively target new venue and restaurant openings and top restaurants that have the maximum impact to our network and business.
  • Collaboration:

    Work closely with other Tripleseat teams, including Account Management, Inside Sales, and Customer Support, to ensure customer success and revenue maximization.
  • Contract Negotiation & Proposal Preparation:
    Prepare detailed proposals and negotiate contracts, ensuring both customer satisfaction and Tripleseat's interests.
  • CRM & Reporting:
    Keep accurate and up-to-date CRM records and provide regular reports on pipeline status and sales activities.
  • Market Expertise:
    Stay updated on competitive trends and market dynamics to position Tripleseat effectively and respond to customer queries. Develop and execute a go-to-market strategy specific to your assigned territory. Use existing industry relationships to secure top-level meetings at restaurants, unique venues, and groups in your assigned territory.
  • Other related duties as assigned.
Knowledge, Skills, And Abilities Required
  • Sales Acumen:
    Demonstrated success in achieving quota in software or SaaS sales, preferably with experience in hospitality software sales.
  • Industry Knowledge:
    In-depth understanding of the hospitality industry and its technology needs.
  • Communication

    Skills:

    Strong interpersonal skills, with the ability to clearly articulate technical solutions and engage with a diverse base of prospects.
  • Software Demonstrations:
    Ability to effectively present Tripleseat software to prospects, ensuring they understand its benefits and capabilities in resolving their specific needs.
  • Time Management:
    Proven ability to handle multiple sales cycles simultaneously while managing time effectively.
  • Problem Solving:
    Strong analytical mindset with the ability to resolve complex customer issues.
  • Team

    Collaboration:

    Ability to work effectively in cross-functional teams, collaborating with different departments to ensure customer success.
  • Values Alignment: A customer-focused attitude and the ability to build rapport across teams.
Preferred Experience
  • SaaS or Hospitality Sales: 1-3 years of experience in hospitality software sales, with a strong network within the industry. Demonstrated success in achieving quota in software sales and/or SaaS sales.
  • Sales in Short Sales Cycles:
    Experience in driving sales in a fast-paced, short sales cycle environment.
  • Territory-Specific Sales:
    Proven experience managing sales in a specific territory, with a demonstrated understanding of local markets and customer needs.
  • Remote Work:
    Experience working in a remote sales role with high independence.
  • Technical…
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