The Director, Sales is responsible for leading and scaling Tripleseat's Account Executives - SMB team, which is focused on driving new business revenue through selling our core product to small and medium-sized restaurant businesses. This role is both strategic and tactical-owning the recruitment, development, and performance of a quota-carrying team while ensuring alignment to key business goals and market opportunities.
This leader champions a "Hospitality First" sales strategy-prioritizing a deep understanding of the hospitality industry and our Ideal Customer Profile (ICP). The Director must ensure that every sales interaction reflects a consultative, empathetic approach grounded in the needs of restaurant operators and clearly articulates how Tripleseat drives operational impact and business value.
The Director is accountable for driving quota attainment, improving average sales price (ASP), KPI analysis and supporting the rollout and adoption of new go-to-market programs. This high-impact, field-facing leadership position requires strong sales acumen, coaching ability, and deep operational insight.
Location: This role will be in-office based in our Boston, MA office, with a schedule of Monday through Thursday in the office and Friday remote.
Travel Expectations: The ideal candidate will be required to complete initial onboarding at our Concord, MA office. Will require 25-50% travel to support sellers in the field, participate in industry events, and strengthen customer relationships.
Core Responsibilities
Build, lead, and retain a team of high-performing Account Executives - SMB, with full accountability for hiring, onboarding, coaching, and development.
Drive revenue through consistent pipeline conversion, average deal size growth, and rep productivity across the team.
Foster a team culture grounded in "Hospitality First", ensuring every seller understands the unique needs, challenges, and buying behaviors of our restaurant ICP.
Deliver clear sales coaching on discovery, positioning, objection handling, and ROI-based closing strategies aligned with our core product value.
KPI management across all aspects of the Sales Process
Establish strong pipeline discipline and forecasting accuracy using Salesforce and related sales tools.
Lead the rollout and adoption of new sales programs, pricing models, messaging updates, and go-to-market strategies.
Partner with Sales Enablement and Revenue Operations to implement playbooks, improve onboarding, and support continuous development.
Collaborate cross-functionally with Marketing, Product, and Customer Success to ensure ICP alignment, seamless handoffs, and feedback loops that improve the customer experience.
Conduct weekly 1:1s, deal strategy sessions, forecast reviews, and team meetings reinforcing accountability, execution, and results.
Other related duties as assigned
Knowledge, Skills, and Abilities Required
Proven success managing full-cycle sales teams in a high-velocity SaaS model.
Strong experience recruiting, coaching, and developing quota-carrying Account Executives.
Deep understanding of ICP definition, buyer personas, and restaurant-industry dynamics, particularly in the SMB segment.
Demonstrated ability to increase revenue, improve average sales price, and drive scalable sales execution.
Strong familiarity with Salesforce and data-driven approaches to managing team performance, forecasting, and pipeline health.
Expertise in sales strategy, program adoption, and performance optimization.
Excellent interpersonal, coaching, and communication skills.
The ability to lead through ambiguity and drive results in a high-growth, fast-paced environment.
Collaborative mindset with experience working cross-functionally to align GTM strategy.
Preferred Experience
5+ years of SaaS sales leadership experience, including at least 3 years managing quota-carrying AEs in an SMB model.
Track record of exceeding team quotas and implementing scalable sales programs.
Prior experience in hospitality tech or service-based industries is strongly preferred.
Experience with sales enablement platforms, CRM reporting, and forecasting tools.
Bachelor's degree in Business, Marketing, or related field required; MBA or advanced degree preferred.
Base Compensation Range: $100,000 - $115,000 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.
