Remote Embedded Sales Jobs in Chicago, IL (NOW HIRING)

We are seeking a high-impact Director of Sales Enablement to own the systems, programs, and culture that make our sales teams faster, sharper, and more effective. This leader will build and scale the enablement function from the ground up - designing onboarding, training, playbooks, and coaching infrastructure that directly move the needle on rep productivity and revenue performance.

This is a strategic yet deeply operational role for someone who bridges the gap between vision and execution. You'll be embedded in the business - analyzing performance gaps, partnering with sales leadership, and turning insights into programs that change rep behavior and drive results. You'll bring a builder's mindset and a bias for measurement, ensuring every enablement investment can be tied back to outcomes.

This role is remote-friendly with hybrid flexibility.

• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.

• Enablement Leadership: 7+ years of experience in sales enablement, with a track record of building and scaling programs in a high-growth environment
• Program Design: Demonstrated ability to design structured, scalable training and onboarding programs that measurably improve sales performance
• Coaching Partnership: Strong experience partnering with frontline sales managers to build coaching cultures and develop rep skills at scale
• Data-Driven Mindset: Expertise in defining enablement metrics and using data to identify gaps, prioritize initiatives, and prove impact
• Content and Curriculum Development: Proven ability to build compelling playbooks, certification programs, and training content that reps adopt and use in the field
• 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
• Strong Communicator: Exceptional ability to influence without authority, build trust with sales leaders, and present clearly to senior stakeholders
• Agility: A self-starter who thrives in fast-paced, high-growth environments where the playbook is still being written

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.