Director, Sales Job at Tripleseat (Boston)

Job Description

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.

Job Responsibility

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

Requirements

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
Bachelor’s degree in Business, Marketing, or related field required

Nice to have

2+ years of SaaS sales leadership experience 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
MBA or advanced degree preferred

What we offer

Competitive Medical, Dental, and Vision Insurance
Company Paid Life Insurance, Short- and Long-Term Disability Plans
401(k) with Company Match
Parental Leave
Flexible Paid Time Off
Pet Insurance

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