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Jobs(31,365)/Sales Manager Role(509)/Engine (48) - Director, Sales Enablement
Engine

Engine - Director, Sales Enablement

Chicago, Illinois, United States - Hybrid$180k - $180k+ Equity2mo ago
In OfficeDirectorNASales ManagerTelemarketerCoachingSales EnablementCurriculum DevelopmentProduct MarketingTraining Development

Requirements

• Enablement Leadership: 7+ years of experience in sales enablement, with a track record of building and scaling programs in a high-growth environment • Enablement Leadership • Program Design: Demonstrated ability to design structured, scalable training and onboarding programs that measurably improve sales performance • Program Design • Coaching Partnership: Strong experience partnering with frontline sales managers to build coaching cultures and develop rep skills at scale • Coaching Partnership • Data-Driven Mindset: Expertise in defining enablement metrics and using data to identify gaps, prioritize initiatives, and prove impact • Data-Driven Mindset • Content and Curriculum Development: Proven ability to build compelling playbooks, certification programs, and training content that reps adopt and use in the field • Content and Curriculum Development • Strategic Operator: Strategic thinker who can also execute — comfortable operating at the 30,000-foot level and rolling up their sleeves when the work demands it • Strategic Operator • Strong Communicator: Exceptional ability to influence without authority, build trust with sales leaders, and present clearly to senior stakeholders • Strong Communicator • Agility: A self-starter who thrives in fast-paced, high-growth environments where the playbook is still being written • Agility • Applications for this role will be accepted through 9/1/2026 or until the role is filled. We encourage you to apply early, as we may begin reviewing applications before the deadline. • CompensationOur compensation packages are based on several factors, including your experience, expertise, and location. In addition to a competitive base salary, total compensation may include equity and/or variable pay (OTE). Your recruiter will share your complete compensation package as you move through the process.

Responsibilities

• Enablement Strategy and Execution: Own the end-to-end enablement roadmap, setting priorities in partnership with sales leadership and ensuring programs are aligned to company growth goals. Translate strategy into structured, repeatable frameworks that the team executes against. • Enablement Strategy and Execution: • Onboarding and Ramp: Set the strategic direction for how new sales hires ramp to productivity. Define clear benchmarks, identify gaps in the existing onboarding experience, and partner with program owners to ensure those gaps are closed before they impact performance or retention. • Onboarding and Ramp: • Ongoing Training and Skill Development: Use data and field observation to diagnose performance gaps across the sales organization. Establish the strategic framework for how those gaps are addressed — ensuring the right training reaches the right people at the right time. • Ongoing Training and Skill Development: • Playbook and Content Development: Define what "great" looks like in terms of messaging, talk tracks, and competitive positioning. Partner with the teams responsible for building and maintaining content to ensure the field always has what it needs. • Playbook and Content Development: • Coaching Infrastructure: Build the strategy and infrastructure that enables frontline managers to coach consistently and effectively. Equip managers with frameworks and tools, and hold the standard for what quality developmental feedback looks like across the org. • Coaching Infrastructure: • Measurement and Impact: Define the KPIs that matter — ramp time, quota attainment by tenure, win rates, skill assessment scores — and use them to surface where the org has gaps and where enablement investments should be directed next. • Measurement and Impact: • Cross-Functional Partnership: Serve as the strategic connective tissue between Sales, Marketing, Revenue Operations, and Product. Ensure that changes in messaging, process, or positioning are adopted consistently across the field. • Cross-Functional Partnership:

Benefits

• $180,000—$210,000 USD • The Engine Edge: Perks & CompensationWe believe in rewarding great work with great benefits: • Compensation: Competitive base pay tied to role and experience, with opportunities for bonuses, commissions, and equity. • 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. • Environments for Success: • Perks and benefits may vary based on employment type, location, and more. • Ready to Build the Future of Work Travel?Join us on our mission to transform how work travel works—for businesses, for travelers, and for the industry. Apply now and let’s make travel simpler, smarter, and more enjoyable—together. • Ready to Build the Future of Work Travel?

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