Sales Training Manager

Engine; Chicago (IL); Hybrid; USD 105,000 - 145,000; Full time

Benefits offered by this job

Hybrid work model

Equity for all employees

Potential bonuses/commissions

Job summary

Engine is seeking a Sales Training Manager to scale its post-onboarding skills program across five business units. You will coordinate sessions, facilitate workshops, and drive certifications while partnering with Directors of Revenue Enablement and onboarding teams.

Your role blends design, coaching, data, and AI-driven content to elevate customer-facing reps across the org. You’ll work in a hybrid-hub environment from Denver or Chicago, bringing strong facilitation, organization, and

Qualifications

• 2+ years in enablement or training roles.
• Experience facilitating workshops, role-plays, and coaching sessions.
• Highly organized with calendar and logistics management.
• Proven ability to build relationships with reps and leaders across teams.
• Comfort with data to demonstrate training impact and behavior change.
• Willingness to learn sales skills, program design, and feedback.
• Tech-savvy with CRM/enablement tools and AI-enabled platforms.

Responsibilities

• Lead competency framework design and rework for multiple business units.
• Coordinate and manage program logistics, cohorts, and enrollment with cross-BU teams.
• Run sessions, role-plays, and coaching, in-person and virtual.
• Create coaching guides and scorecards for managers to reinforce skills.
• Onboard new hires and partner with onboarding teams to shape ongoing development.
• Measure participation, certification rates, and business outcomes; iterate accordingly.

Skills

Enablement

Training

Facilitation

Organization

Relationship building

Data-driven

AI tools

Growth mindset

Tools

Salesforce

Momentum

GTMBuddy

LetterAI

Job description

About Engine

Engine is the AI-native platform for intelligent travel. For a decade, Engine has built the proprietary technology and supply behind modern business travel, serving over 40,000 customers and nearly 2 million travelers, along with leading travel and AI companies that build on Engine's infrastructure. One system powers business travel, group travel, human agents, and AI agents. That work has earned Engine recognition as TravelTech's Reservation Platform of the Year (2026), a spot on Inc.'s Power Partners list (2026), and one of Built In's Best Places to Work (2020–2026).

Mission & Opportunity

We're looking for bold, ambitious people to help redefine how businesses manage and experience travel. Working here, you can expect exponential growth, an ambitious pace, full ownership, and high-caliber colleagues who push you to do the best work of your career. Every hire raises the bar. Come outpace the ordinary and build the future of travel with us.

Your Mission:

As Sales Training Manager, you'll help bring Engine's post-onboarding sales skills program to life for every customer-facing and prospect-facing rep across our five business units— Travel/Spend, Groups, Supply/Partnership, Omni, OBT. The program already exists. It's small today, and we're reworking it to scale into a skills‑and‑competency-focused program that keeps reps sharpening how they sell, serve, and grow customers long after onboarding ends. Our Revenue Enablement Managers are each embedded in one business line. You'll help run a central program that spans all of them. Day to day, that means a lot of coordination and project management, time spent leading sessions, and helping track whether the program changes behavior and results. You'll build it in tandem with our existing Sales Training Managers and the Director of Revenue Enablement, as part of a team we're building out based on impact. You'll report directly to the Director of Revenue Enablement. New‑hire onboarding is owned by our onboarding team, and you'll work closely with them, facilitating onboarding sessions as needed, so the gaps you see early shape how the everboarding program develops.

Competency Program Design & Rework

• Competency Framework: Help build the core skills every customer‑facing and prospect‑facing rep needs, such as discovery, value articulation, objection handling, negotiation, and account growth, and what "great" looks like at each level, in tandem with the STM team and the Director
• Program Rework: Help assess what's working in the current program and what isn't, and help redesign curriculum, skill paths, and certifications so they work across five business units and many roles.
• Skills‑Based Certification: Help build and run certifications where reps show the skill, not just pass a quiz, through role‑plays, recorded pitches, and call reviews scored against clear rubrics.
• Built to Scale: Create modular content and practice that each business unit can tailor without starting over, so the program can grow from small to company‑wide.
• AI‑First Enablement: Build AI first. Use AI to create skill content, role‑plays, practice scenarios, and call coaching at scale, so a small team can give every rep across all five business units more practice and faster feedback.

Facilitation & Delivery

• Lead the Room: Facilitate skills workshops, role‑plays, and practice sessions, in person and virtually, for reps at every tenure level in every business unit.
• Call Coaching: Use conversation intelligence tools (e.g., Momentum) to run call‑review and coaching sessions, highlight great calls, and turn real conversations into practice.
• Manager Reinforcement: Help create coaching guides and scorecards so front‑line managers can reinforce skills between sessions, not just in the classroom.
• Onboarding Support: Facilitate onboarding sessions as needed alongside our onboarding team.

Coordination & Program Management

• Leverage AI to manage the Logistics: Manage the calendar, cohorts, logistics, communications, and enrollment for a program that reaches every go‑to‑market team.
• Cross‑BU Coordination: Work with teams across five business units on scheduling and tailoring, and keep requests organized and moving so the core program stays on track.
• One Team, One Program: Share ownership, content, and standards with the other Sales Training Managers so every rep gets one consistent experience.
• Cross‑Functional Collaboration: Work with the Revenue Enablement Managers, Product Marketing, Revenue Operations, and Product so the skills program fits alongside each business line's enablement.
• Onboarding Partnership: Work in tandem with the onboarding team to spot skill gaps early and use them to shape and develop the everboarding program accordingly.

Measurement & Impact

• Support Measurement: Help track how the program is measured, such as participation and certification rates, competency scores, behavior change in call reviews, and business outcomes like conversion, win rate, and retention or expansion, using the measures set with the STM team and the Director. [TBD: confirm program KPIs]
• Spot Behavior Change: Pull together certification and competency data, call reviews, and Salesforce performance data to show whether skills are showing up on real calls and moving results.
• Report & Iterate: Help prepare program updates for the Director of Revenue Enablement, and share what you're seeing so the team can decide what to scale, fix, or stop.
• Enablement Tech Stack: Help reps get full value from our learning and practice tools. Work with our tools and systems team so new tools actually get adopted.

Relationships & Stakeholders

• Trusted Partner Across the Business: Build strong relationships with reps, front‑line managers, and leaders in every business unit so the program becomes something they ask for, not something they're sent.
• Champions & Feedback: Bring in top performers and managers as champions and subject‑matter experts, and build feedback loops with reps and leaders so the program keeps getting better.
• Bias for Impact: Keep the focus on the work that moves revenue, and flag to the STM team and the Director when requests start to pull the program off course.

Why This Role: AI-First at Engine

At Engine, AI isn't a side project. It's how we work. Our access to create with AI is incredibly unique, and this role is a rare chance to get exposure to a ton of AI tools and learn from the best. The expectation is simple: AI first, to create scale. For this role, AI is how a small program grows to reach every customer‑facing rep across five business units, with more practice, faster feedback, and content that keeps up with the business. Building this way grows Engine, and it grows your skill set too. If you're growth‑minded and excited to build what's next, you'll thrive here.

What You’ll Bring to Engine

• Experience: 2+ years in enablement, training. Bonus for a time in seat in a sales a customer‑facing role, or a program or project management role.
• Facilitation: You're comfortable leading a room, in person or virtually, and you're excited to run role‑plays and coaching sessions that help people sell better.
• Organization: You're highly organized and can keep calendars, cohorts, logistics, and communications on track across many teams.
• Relationship Builder: You build trust quickly with reps and leaders across very different teams, and you enjoy working with lots of stakeholders.
• Curious About Data: You're comfortable working with numbers and want to learn how to show whether training actually changes behavior and results.
• Coachable & Eager to Learn: You want to learn sales skills, adult learning, and program design from an experienced team, and you act on feedback quickly.
• Tech‑Savvy: Bonus points if you're fluent in Salesforce, conversation intelligence tools (e.g., Momentum), and enablement/LMS platforms (e.g., GTMBuddy, LetterAI).
• AI‑First Mindset: You reach for AI first to create scale, and you're excited to get hands‑on with a wide range of AI tools. You're growth‑minded and eager to keep building your skill set.
• Mindset: You're ready to roll up your sleeves, collaborate as part of a team, and deliver results that matter.

Nice to Have

• Prior experience in sales enablement, sales training, or revenue enablement is a strong plus.
• Program or project management or PMO experience is a strong plus, especially coordinating work across several teams.
• Experience building training content, role‑plays, or certifications, or a working knowledge of B2B sales methodologies (e.g., MEDDPICC, Challenger, Sandler).
• Background in B2B travel, hospitality, or marketplace businesses.
• Experience carrying a quota or working as a rep or account manager.
• Examples of skill practice, role‑plays, or coaching content you've built with AI.

Location & Travel

This role is preferably based in or near one of our hubs in Denver, CO or Chicago, IL, and we prefer candidates who are local to one of those markets. We're open to candidates elsewhere in the US for the right fit. Expect to travel about one week per month to facilitate sessions and work with teams in person, plus major company events, so openness to travel is a must.

Base Pay Range

$104,800—$145,000 USD

Compensation

Our compensation packages are based on several factors, including your experience, expertise, and location. In addition to a competitive base salary, all roles receive equity. Depending on the role, total compensation may also include an annual bonus. Your recruiter will share your complete compensation package as you move through the process.

The Engine Edge: Perks & Compensation

• Compensation: Competitive base pay tied to role and experience, with equity for all employees. Some roles are also eligible for bonuses or commissions.
• Benefits: Check out our full list at engine.com/culture
• Environments for Success: Different roles have different needs in terms of the environments that drive success which is why we have a hybrid-hub model. Whether you are in one of our amazing offices or fully remote, we'll make sure you have what you need to succeed.

Perks and benefits may vary based on employment type, location, and more