Sales Enablement Director

2 weeks ago


Chicago, Illinois, United States Envoy Global, Inc. Full time $125,000 - $145,000

Envoy Global is a proven innovator in the global immigration space. Our mission combines our industry-leading tech platform with holistic service to streamline, simplify and expedite the immigration process for employers and individuals.

We have an opening within Envoy's dedicated Sales team for an experienced Sales Enablement Director to join us on a full time, permanent basis. As our Sales Enablement Director here at Envoy Global you will build and lead the programs, tools, and training initiatives that elevate the effectiveness of our global sales organization. You will also partner with Sales, Marketing, Product, Attorneys/legal service providers, and Revenue Operations leadership to create a world-class enablement function that improves how our teams engage prospects and customers from pipeline management through contract negotiation. Our Ideal Sales Enablement Director is passionate about equipping our teams with the skills, processes, and resources needed to execute consistently across the sales cycle, elevate pitching and demos, strengthen deal management discipline, and increase win rates.

As our Sales Enablement Director, you will be required to: 

Sales Effectiveness & Training
  • Develop and deliver comprehensive training programs focused on value-based messaging, contract negotiation, and deal management.
  • Build a structured onboarding program to ramp new hires quickly to full productivity.
  • Partner with Product Marketing, Product, and Attorneys/legal professionals to ensure consistent messaging, positioning, and support during pitches and demos.
  • Develop coaching frameworks and tools to equip frontline managers to effectively coach their teams in deal execution, pipeline reviews, and performance improvement.
  • Design certification programs to validate rep readiness in core skills such as pitching, demos, discovery, and negotiation.
Enablement Tools & Content
  • Create sales playbooks, pitch decks, demo frameworks, and objection-handling guides tailored to different buyer personas and deal stages.
  • Implement scalable enablement tools (LMS, content management, demo tools) to ensure reps have access to the right resources at the right time.
  • Collaborate with Marketing to ensure demand-generation content is aligned with the sales cycle and effectively leveraged by the field.
  • Align enablement programs with the customer buying journey to ensure sales teams are engaging prospects with the right message, content, and support at each stage.
Pipeline & Deal Management
  • Partner with Sales Leadership and RevOps to improve pipeline hygiene, forecasting accuracy, and deal progression.
  • Introduce best practices for opportunity reviews, deal strategy sessions, and competitive positioning.
  • Coach frontline managers and reps on pipeline management discipline and deal execution excellence.
  • Collaborate with Sales Ops and Product Marketing to analyze win/loss data, feeding insights into training programs and sales strategy adjustments.
Performance & Metrics
  • Establish clear enablement KPIs tied to productivity, quota attainment, and win rates.
  • Track adoption and effectiveness of enablement initiatives and continuously optimize programs based on data and feedback.
  • Ensure alignment with the quota model, forecasting cadence, and CRO-level revenue goals.
  • Develop scalable enablement programs that can be localized to meet the needs of sales teams across U.S. and global markets.

To apply for this role, you should possess the following skills, experience and qualifications: 

  • 10+ years of experience in sales enablement, sales leadership, or related roles within SaaS, technology, or services industries.
  • Proven success improving win rates, sales productivity, and scaling global sales teams.
  • Deep expertise in sales methodologies (MEDDICC, Challenger, SPIN, or similar).
  • Strong background in designing training programs, playbooks, and enablement content.
  • Experience implementing and managing enablement tools (LMS, Highspot, Seismic, or equivalent).
  • Ability to partner across functions—Sales, Marketing, Product, Attorneys/Legal, and Operations—to align execution to strategy.
  • Excellent communication and facilitation skills with executive presence.

ANNUAL SALARY RANGE- $125, $145,000.00

Notice at Collection for California Applicants:

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