Account Executive - Hotels (Chicago)
Tripleseat Software
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 - Hotels at Tripleseat, you will be a vital part of a dynamic team responsible for driving revenue growth within an assigned territory. This is a remote, quota-carrying role with a dual mandate: win net-new hotel accounts and strategically grow an existing customer portfolio. This role targets a diverse buyer universe — from independent boutique properties and SMB hotel operators to mid-size management groups and franchise owners — selling a platform that transforms how hotels manage event sales and group bookings.
The ideal candidate is someone who brings hospitality industry knowledge, enjoys prospecting and building new relationships, while also acting as a trusted partner to existing customers. Success in this role comes from balancing both—bringing energy and consistency to new logo acquisition, and thoughtfulness and strategy to growing an existing portfolio. This role collaborates cross-functionally with Marketing, Customer Success, Product, and Implementation teams to support customers throughout the entire lifecycle.
Location: This position is open to candidates eligible to work in the United States, located in the Chicago area.
Travel Expectations: The ideal candidate will be required to complete initial onboarding at our Concord, MA office. This role will require 25% travel within their assigned territory – including customer meetings, tradeshows, conferences, and company events.
Core Responsibilities
• Prospect a diverse hotel universe — independents, SMB properties, management groups, and franchise owners — via ZoomInfo, Outreach, LinkedIn Sales Navigator, Brizo, and direct outreach; book a minimum of 3 qualified new meetings per week.
• Build and maintain a new-business pipeline at 3× quota with accurate weekly forecasting; develop a referral network with hospitality tech vendors, consultants, and industry partners.
• Lead full-cycle sales processes from outreach through discovery, tailored demo, proposal, negotiation, and close — applying NEAT Selling to qualify on Need, Economic Impact, Access to authority, and Timeline.
• Deliver customized product demonstrations mapped to the operational realities of each hotel type; engage GMs, DOSMs, Revenue Leaders, and ownership groups; navigate multi-stakeholder deals with precision.
• Manage an assigned portfolio of hotel accounts as the primary commercial point of contact—develop growth plans, lead Executive Business Reviews, and identify opportunities for upsell, cross-sell, and multi-property expansion.
• Monitor portfolio health (adoption, engagement, renewal timelines) and proactively address risks; build strong, multi-threaded relationships across property, regional, and ownership levels to support long-term success.
• Partner closely with Customer Success to drive account health and adoption—while CS supports day-to-day success, the AE owns the overall commercial relationship. Track and forecast expansion ARR with the same level of discipline as new business pipeline.
• Represent Tripleseat at hotel and hospitality conferences, trade shows, and local events; maintain current knowledge of competitive landscape and hotel technology trends to sharpen prospecting, retention, and expansion conversations.
• Maintain accurate opportunity data and activity in Salesforce across both pipelines; forecast new-logo and expansion revenue using stage-based methodology; share voice-of-customer insights cross-functionally.
Knowledge, Skills, and Abilities Required
• Hunter Mentality: A self-motivated prospector who takes ownership of pipeline generation and doesn’t rely solely on inbound leads to achieve quota.
• Portfolio Growth & Retention Instinct: Proactively identifies expansion signals, manages renewal risk before it materializes, and builds multi-threaded account relationships — recognizing that protecting and growing the base is a distinct skillset requiring separate planning and a longer time horizon than new-logo selling.
• NEAT Selling & Consultative Expertise: Qualifies on genuine business Need, builds Economic Impact cases, secures Access to authority, and drives mutual Timeline — applied equally to new prospects and existing-account expansion conversations.
• Hospitality Business Acumen: Fluent in hotel operations — revenue management, group/event sales dynamics, ownership structures, and the financial pressures facing operators from independent SMBs through management groups.
• Executive Communication & Demo Skills: Compelling written and verbal communicator who engages everyone from a property GM to a PE-backed ownership group; delivers insight-driven demos that make prospects feel the value, not just see the features.
• Dual-Motion Time & Territory Management: Structures time to balance new-business prospecting with portfolio management; segments and prioritizes a mixed book without letting either motion slip.
• CRM & Sales Tech Proficiency: Proficient in Salesforce, Outreach, ZoomInfo, and LinkedIn Sales Navigator; uses the CRM to manage both prospecting cadences and portfolio health.
Preferred Experience
• 3–5 years of quota-carrying SaaS sales experience with responsibility for both new-logo acquisition and existing account growth — ideally within the hotel or broader hospitality vertical.
• Demonstrated success running a mixed book: active new-business pipeline alongside structured account plans, EBRs, and expansion ARR closes (upsell, cross-sell, multi-property rollouts, renewals).
• Experience selling across diverse hotel segments: independent SMB properties, boutique hotels, franchise operators, and mid-size management companies or ownership groups.
• Background in hotel operations, group/event sales, revenue management, or hotel technology is a significant advantage.
• Proven application of NEAT Selling or similar qualification-forward methodologies; track record of disciplined discovery and pipeline accuracy.
• Familiarity with hotel technology ecosystem (PMS, CRM, sales & catering, RMS); able to speak credibly to integrations and platform ROI in both new-business and expansion contexts.
Base Compensation Range: $90,000 - $110,000 annually
Base salary is one component of total compensation. Employees may also be eligible for an annual bonus or commission.
The above represents the expected base compensation range for this job requisition. Ultimately, in determining your pay, we’ll consider many factors including, but not limited to, skills, experience, qualifications, geographic location, and other job-related factors.
Tripleseat truly values its employees and places a high emphasis on their well-being and happiness. We understand that our people are the driving force behind its success and strive to create a positive and supportive work environment. We love what we do and who we get to do it with! Here are some of the awesome benefits that Tripleseat offers to its employees:
· Competitive Medical, Dental, and Vision Insurance: Tripleseat provides its employees with comprehensive medical, dental, and vision insurance coverage, ensuring that their health and well-being are taken care of.
· Company Paid Life Insurance, Short- and Long-Term Disability Plans: Tripleseat takes care of its employees by providing them with life insurance coverage, as well as short and long-term disability plans to protect them in case of unforeseen circumstances.
· 401(k) with Company Match: Tripleseat offers a 401(k) retirement plan to its employees, and also provides a company match, helping employees save for their future and plan for retirement.
· Parental Leave: Tripleseat understands the importance of work-life balance and offers parental leave to employees who become parents through birth, adoption, or foster care, allowing them to bond with their new family members without worrying about their job security.
· Flexible Paid Time Off: Tripleseat believes in the importance of work-life harmony and offers flexible paid time off to its employees, giving them the flexibility to take time off when needed and maintain a healthy work-life balance.
· Pet Insurance: Tripleseat recognizes the importance of pets in employees' lives and offers pet insurance to help them take care of their furry friends and ensure their well-being.
At Tripleseat, we place a high value on our employees' well-being and happiness, recognizing that they are the driving force behind our success. We are committed to fostering a positive and supportive work environment. We take pride in our work and the collaborative spirit of our team We are proud to be an equal-opportunity employer, not discriminating based on race, color, ethnicity, ancestry, religion, sex, national origin, sexual orientation, age, citizenship status, marital status, disability, gender identity, gender expression, veteran status, or genetic information. We are dedicated to fostering a culture of inclusion, diversity, and equity. Tripleseat empowers all team members to realize their full potential. Everyone Valued – Everyone Included.
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