Senior Sales Enablement Specialist

This is a fully remote position, open to applicants in United States.

📋 Description

• Collaborate with the Senior Manager to develop enablement strategies and implement field-facing initiatives.

• Create and deliver in-person workshops, Microsoft Teams bootcamps, coaching sessions, and provide ongoing field support.

• Develop and manage go-to-market materials such as discovery guides, battle cards, competitive positioning documents, playbooks, demo flows, use case narratives, ROI calculators, and value justification templates.

• Assist sales representatives before, during, and after deals through training, access to collateral, coaching, objection handling, guidance on complex scenarios, win/loss analysis, and continuous improvement efforts.

• Evaluate ramp-up times, time-to-first-deal, average deal size, win rates, quota achievement, collateral usage, and enablement ROI.

• Act as a subject matter expert on EPM platforms and equity services solutions, translating technical features into business impact.

• Identify capability gaps, mentor underperforming representatives, and facilitate behavioral change.

• Oversee new-hire onboarding, bootcamps, field ride-alongs, and progression frameworks.

• Conduct or deliver Sales Kickoffs, product launch training, competitive response programs, and regional training events.

• Utilize Claude AI to automate the creation of collateral drafts, customize coaching feedback, analyze win/loss data, and generate sales scenarios while ensuring quality control.

• Present enablement metrics and business-impact suggestions to the Senior Manager and sales leadership.

• Work collaboratively on LMS, collateral management, Salesforce reporting, and maintain Claude integration.

⛳️ Requirements

• Over 5 years of progressive experience in Sales Enablement, Sales Training, Sales Operations, or Sales Coaching within enterprise software or B2B SaaS.

• Experience in supporting both enterprise and mid-market sales teams.

• Demonstrated expertise in Enterprise Performance Management platforms, including planning, budgeting, analytics, and forecasting.

• Background in selling or supporting equity services, employee ownership solutions, or similar financial services.

• Outstanding facilitation and training delivery skills for both virtual and in-person audiences.

• Proven track record of creating GTM collateral from scratch, including playbooks, battle cards, discovery guides, competitive positioning documents, case studies, demo flows, and ROI/value calculators.

• Proficient in MEDDPICC and Value Selling frameworks, including teaching and coaching representatives.

• Comfortable with analytics, SQL, dashboards, or Salesforce reporting; capable of establishing KPIs and measuring program ROI.

• Personal accountability for field-team productivity, quota achievement, and deal velocity.

• Practical experience with Claude AI or similar LLMs for content generation, win/loss analysis, scenario simulation, or workflow automation.

• Excellent written communication skills and the ability to distill complex topics into buyer-friendly narratives.

• Preferred: experience with an EPM software vendor; selling to CFO, VP Finance, or Controller personas; familiarity with Salesforce reporting, Tableau, Looker, sales enablement platforms, LMS systems, Sales Kickoffs, mentoring other enablement professionals, or published thought leadership.

🏝️ Benefits

• Salary range of $88,000.00–$111,000.00 USD annually; for non-sales positions, only base salary applies, and additional bonus eligibility may be considered.

• Commission target included for sales roles.

• Equal employment opportunity.

• Confidential handling of applicant information in accordance with EEO guidelines.