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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.

The Opportunity

We’re looking for a Sales Training & Enablement Manager to design, deliver, and continuously improve our sales onboarding and training programs across all segments—from SMB to Enterprise. Reporting to the VP of Revenue Operations & Strategy, this role sits at the intersection of sales, marketing, and people development. You’ll build the foundation for scalable onboarding, manage our learning management system (LMS), and drive measurable improvements in ramp time, sales velocity, and team productivity.

If you’re passionate about coaching sellers, building content that sticks, and partnering cross-functionally to create a world-class enablement experience, this is your opportunity to make a lasting impact.

What You’ll Own:

New Hire Onboarding & Continuous Training

+ Design and deliver a best-in-class onboarding experience for all sales roles across SMB, Mid-Market, and Enterprise.

+ Own the onboarding calendar, curriculum, and certification process from pre-boarding through full ramp.

+ Partner with Sales Leadership, People & Talent, and Marketing to ensure training aligns with GTM priorities and company values.

+ Measure ramp time, productivity milestones, and skill acquisition—using data to continuously optimize the program.

Learning Management System (LMS) Ownership

+ Manage the end-to-end operation of the LMS (content library, user access, analytics, certification paths).

+ Create and upload engaging, trackable modules covering product, process, and skill-based content.

+ Partner with RevOps, Product Marketing, and Customer Success to ensure content is current, relevant, and accessible.

+ Leverage usage analytics to measure adoption and ROI of learning programs.

Role Play, Coaching & Certification

+ Lead regular role-play sessions focused on SPIN methodology, objection handling, storytelling, and consultative selling.

+ Facilitate skill assessments and certifications to validate readiness and drive accountability.

+ Deliver live and virtual enablement sessions on core competencies—product knowledge, competitive positioning, and GTM strategy.

Performance Enablement & Metrics

+ Build frameworks and scorecards to track onboarding performance, ramp-to-productivity, and training ROI.

+ Collaborate with the Data & Insights team to analyze sales performance pre- and post-training.

+ Identify trends, skill gaps, and enablement opportunities across teams and segments.

Cross-Functional Partnership

+ Collaborate with Sales Leadership to align training with pipeline goals, quota attainment, and buyer journey needs.

+ Partner with Marketing to roll out new campaigns, messaging, and product launches with clarity and consistency.

+ Work with Customer Success and Hospitality teams to build training that supports the full customer lifecycle.

+ Contribute to enablement initiatives that reinforce company culture and hospitality-driven selling.

Content Development & Communication

+ Develop modular, scalable enablement content (playbooks, decks, cheat sheets, videos).

+ Align content across teams to maintain a consistent narrative from prospecting to renewal.

+ Ensure training programs reinforce both the art and science of sales—balancing soft skills with data-driven rigor.

What We’re Looking For:

+ 3–6+ years in Sales Enablement, Training, or Sales Leadership within B2B SaaS or hospitality technology.

+ Minimum 2 years direct selling experience—preferably in SaaS, tech, or hospitality sales.

+ Strong understanding of sales methodologies (SPIN, Challenger, MEDDICC, or similar).

+ Experience managing or implementing a Learning Management System (WorkRamp, Lessonly, Seismic, or equivalent).

+ Ability to design and deliver engaging live and virtual training programs.

+ Skilled in content creation (slides, video, documentation) and familiar with sales tech stacks (Salesforce, Outreach, Gong, DealHub, etc.).

+ Data-driven mindset with the ability to analyze performance and recommend improvements.

+ Exceptional communication, facilitation, and interpersonal skills—able to energize and inspire diverse teams.

Success Looks Like:

+ Decreased ramp time and faster time-to-first-deal across all sales roles.

+ Consistent onboarding experience across segments, supported by measurable certification milestones.

+ Increased adoption of sales processes, tools, and methodologies.

+ Improved sales velocity and win rates through skill reinforcement and role-based enablement.

+ A scalable enablement framework aligned with GTM strategy, product updates, and market trends.

+ Engaged, confident sellers who deliver value-driven conversations at every stage of the funnel.

Base Compensation Range:

+ $95,000 - $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.