Senior Manager of CS Enablement

The Senior Manager of CS Enablement owns a meaningful portion of the CS program portfolio. This is not a support role. You will identify what CSMs and Account Managers need to do differently to retain and grow their accounts, build programs that address those gaps, deliver them, and track whether they worked.

This role sits close to the field. You will attend CS leadership meetings, review Gong calls, shadow account reviews, and stay near enough to the post-sale motion that your programs reflect real account dynamics, not a textbook version of what good CS looks like.

CS enablement requires a different instinct than Sales enablement. The buying decision is already made. Your programs need to help CSMs drive adoption, manage executive relationships, identify expansion signals, and recover at-risk accounts, all with buyers who are often overextended and skeptical of additional asks on their time. Candidates who have done that job before coming into enablement will bring a credibility advantage that is difficult to replicate.

What you’ll do

• Own the strategy and execution of Customer Success enablement programs end-to-end, from identifying field needs through launch, reinforcement, and measurement
• Build practical, high-impact learning experiences that help Customer Success teams improve performance in real customer conversations, not just complete training
• Create reinforcement systems that drive adoption after the session ends, including manager coaching frameworks, workflow tools, peer learning, and structured practice
• Manage multiple enablement initiatives simultaneously with strong operational discipline, clear prioritization, and consistent communication across stakeholders
• Stay deeply connected to the business by participating in team meetings, account reviews, and QBR prep sessions while leveraging Gong and Salesforce insights to identify trends, risks, and skill gaps
• Develop scalable, field-ready content that supports Customer Success Managers in renewals, expansion opportunities, executive business reviews, and customer recovery moments
• Partner closely with Customer Success leadership and frontline managers to embed enablement into team operating rhythms, coaching cadences, and day-to-day execution
• Design and facilitate coaching programs, role-plays, and scenario-based learning that help Customer Success teams build confidence, sharpen account strategy, and improve customer outcomes

What success looks like

• NRR trend in the assigned segment following program delivery, compared to pre-program baseline
• Expansion conversion: Upsell and cross-sell attach rate in the assigned segment, as a proxy for expansion motion program effectiveness
• Percentage of accounts in assigned segment receiving a structured EBR on schedule, as a leading indicator of program impact on executive relationship quality
• Highspot engagement rate on assets produced, as a measure of whether field content is actually reaching and being used
• CS front-line manager rating of enablement support quality, collected quarterly

What you’ll bring

• 7+ years in CS Enablement, Sales Enablement, or a post-sale revenue role with direct ownership of program design and delivery
• Experience in programmatic advertising, Connected TV, digital media, or a closely adjacent AdTech environment, CS reps at MNTN manage campaign performance conversations with sophisticated buyers, and your programs need to reflect that reality
• Fluency in CS methodology: value realization, EBR/QBR frameworks, expansion motion, at-risk account management
• Working knowledge of MEDDICC as an account health framework, you need to use it to coach CSMs on account risk, not just Sales reps on deal qualification
• Strong facilitation skills — able to lead experienced CSMs with content that is immediately credible, practical, and grounded in real customer situations
• Proficiency in Gong, Salesforce, WorkRamp, and Highspot

Strongly Preferred

• Direct experience as a CSM, Onboarding Specialist, or Account Manager in an AdTech, CTV, or SaaS environment before moving into an enablement function
• Familiarity with CTV-specific customer conversations: campaign performance reviews, attribution methodology, incremental reach, and renewal justification in a performance-driven buying environment
• Experience building programs for both CSM and AM roles simultaneously, accounting for the different renewal and expansion motions each role runs
• Experience using Gong data independently to build a picture of CS skill health, not just reviewing calls when directed