Ben Rosenberg

Head of Customer Enablement

ChurnZero

sales_enablement
Posted by Ben Rosenberg•

Overview

You're designing and running the customer education function for ChurnZero's CS platform. You'll partner directly with the VP of CX to rebuild how customers learn the product—moving from traditional training to embedded, AI-enabled learning that drives actual product adoption. You're not just delivering training; you're architecting certification paths and in-product education systems.


Role Snapshot

AspectDetails
Role TypeCustomer Enablement Leader
Primary FocusProduct education, certification design, adoption frameworks
Team SizeIndividual contributor or small team (likely 0-2 reports to start)
ScopeAll customer learning - onboarding through advanced product adoption
Internal PartnersProduct, CS ops, CSM team, Marketing
Success MetricProduct adoption rates, time-to-value, certification completion

Company Context

Stage: Unknown (139 employees suggests Series B/C range)

Size: 139 employees

Growth: Building AI agent capabilities into their CS platform, active hiring for strategic roles

Market Position: Established CS platform competing in a crowded category (Gainsight, Totango, Catalyst, Planhat)


Customer Education Reality

Current State: They have "what's worked well" but the VP explicitly says it's time to redesign for 3-5 years out. Translation: you're inheriting something functional but dated.

What You're Building Toward:

  • Embedded learning experiences inside the product itself
  • AI-enabled education (using their own AI agent tech or other tools)
  • Formal certification programs
  • Scalable adoption frameworks that reduce human CSM touch

The Challenge: Most CS platforms have complex feature sets. Customers struggle to move beyond basic usage. You need to get them to actually adopt advanced features without requiring expensive 1:1 CSM time.


What You'll Actually Do

Time Breakdown

Strategy/Design (30%) | Content Creation (25%) | Platform/Tech (20%) | Stakeholder Management (15%) | Delivery/Iteration (10%)

Key Activities

  • Audit and redesign the learning journey: Map out current customer onboarding and training, identify gaps, design the future state for embedded/AI-enabled learning
  • Build certification programs: Create structured learning paths, assessment criteria, and credentialing for different user roles (CS Ops, CSM leaders, analysts)
  • Develop in-product education: Work with Product to design tooltips, walkthroughs, contextual help, and progressive disclosure that teaches while users work
  • Create scalable content: Build video libraries, knowledge base articles, interactive demos, and self-serve resources that reduce repetitive training asks
  • Partner with Product on adoption metrics: Define what "good adoption" looks like for each feature, build measurement frameworks, design interventions for low-usage segments
  • Enable the CSM team: Make sure customer-facing teams know how to guide customers through learning paths and use education as a retention/expansion lever
  • Vendor/platform evaluation: Potentially implement LMS, digital adoption platforms (Pendo/WalkMe/Appcues), or AI tools to deliver education at scale

The Honest Reality

What's Hard

  • You're building the plane while flying it: This is a redesign, not a maintenance role. Customers still need training today while you're building the future system
  • Product complexity: CS platforms have deep feature sets. Explaining segmentation rules, journey orchestration, health scores, and integrations in ways that stick is difficult
  • Measurement is fuzzy: Unlike sales enablement (win rates, ramp time), customer enablement success is harder to quantify. You'll need to establish new metrics
  • Cross-functional dependency: You need Product to build in-product education, Marketing to promote certifications, CS to deliver content. Lots of influence without authority
  • AI is a buzzword: "AI-enabled enablement" sounds good on paper. Figuring out what that actually means in practice requires experimentation and likely some failures
  • Adoption is cultural, not just educational: Even perfect training won't help if customers don't have exec buy-in or resources to implement what they learn

What Success Looks Like

  • Certification program launched with measurable completion rates and adoption correlation
  • Time-to-value for new customers decreases (faster onboarding, quicker feature adoption)
  • CSM team spends less time on "how do I..." questions, more on strategic advice
  • Product usage data shows customers activating advanced features at higher rates
  • You've built a scalable system that works without adding headcount linearly

Who Your "Customer" Is

Primary Audiences:

  • CS Ops professionals who admin the ChurnZero platform
  • CSM leaders who need to train their teams to use it
  • End-user CSMs who use it daily to manage accounts
  • Executives who need to understand dashboards and ROI

What They Care About:

  • Getting to value fast (execs are impatient, they bought this to reduce churn)
  • Not looking dumb in front of their team (CS Ops people need to be the expert)
  • Time efficiency (CSMs are slammed, won't watch hour-long training videos)
  • Practical application ("just show me how to build the segment I need today")

Requirements

  • 5+ years in customer education, enablement, or learning design—preferably in B2B SaaS
  • Experience building certification or structured learning programs from scratch
  • Familiarity with learning platforms (LMS), digital adoption tools, or in-product education strategies
  • Comfortable with ambiguity and designing new frameworks vs. running existing playbooks
  • Strong stakeholder management—you'll partner with Product, CS leadership, and ops without formal authority over them
  • Understanding of customer success metrics and how education drives retention/expansion
  • Bonus: Experience with AI tools for education (adaptive learning, chatbots, content generation)
  • Bonus: Background as a CSM or CS Ops person who knows what customers actually struggle with