CaptivateIQ is transforming the way companies plan, manage, and optimize sales performance. We started by revolutionizing incentive compensation management, and now we’re expanding our platform to solve broader sales planning challenges. Recognized by industry analysts like Forrester and G2 and backed by top-tier investors, including Sequoia, ICONIQ, Accel, and Sapphire Ventures,  we empower high-growth companies like Netflix, Figma, and Stripe with the flexibility and insights needed to drive revenue performance.

Join a talented, fast-growing team committed to solving some of the most complex and impactful problems in sales performance management.

About the Role

We’re looking for a Senior Manager, Customer Enablement to lead this transformation. This is a builder role. Your job will be to reimagine how we enable customers in an AI-forward world, challenge assumptions about what enablement looks like, and build the infrastructure, capabilities, and team to get there.

You’ll own three core functions: the CaptivateIQ Academy (our on-demand learning platform), the Knowledge Center, and trainer-led delivery. You’ll lead a team that touches every stage of the customer lifecycle, from onboarding through expansion, and partner closely with Customer Success, Support, Product, and Professional Services to make sure enablement is a layer that runs through everything.

This is a transformation role, not an operator role. We have established programs. What we don’t yet have is an enablement model built for a world where AI can fundamentally change how content gets created, maintained, and delivered — and where the product itself can be a vehicle for customer learning. That’s what you’re here to build.

Job Location

This is a fully remote opportunity.

What You’ll Own

Build an AI-Native Education Engine

Reimagine what enablement and education means in SaaS. The goal is a system where customers can use the product effectively without spending dozens of hours watching instructional videos. Think AI-powered delivery, adaptive content, and contextual help that meets customers at their point of need rather than asking them to go find it.

Meet Customers Where They Are

Map the real customer journey, identify highest-friction moments, and close the gap between confusion and clarity. Partner with Product and Design to embed contextual guidance, intelligent walkthroughs, and AI-assisted help directly into the product.

Inform Product Direction

Surface enablement data and customer friction patterns back to Product as actionable input - so that self-service gaps aren’t just patched with documentation, but addressed at the product level.

Lead & Grow the Team

Manage and develop a team spanning content, learning experience design, training delivery, and knowledge management. Build AI fluency across the team, set a high bar for experimentation, and coach everyone to measure customer outcomes over education outputs.

Measure What Matters

Define success by product adoption, feature utilization, time-to-value, support deflection, and retention influence, not course completions. Build feedback loops between in-product engagement data and what you build next.

What We’re Looking For

Required

• 6+ years in customer education, enablement, or learning within B2B SaaS, with team leadership experience.

• A transformation track record — you’ve moved programs from traditional, destination-based training toward more embedded, responsive models. You know what it takes and you’ve done it before.

• Real AI fluency. You’ve integrated AI tools into content creation, delivery, or personalization workflows. You can speak concretely about what you’ve tried, what scaled, and what you’d do differently. This is not a “willing to learn AI” role.

• Customer-outcome orientation. You think in terms of adoption, time-to-value, and independence — not course completions.

• Operational rigor. You can run a high-quality content operation (accuracy, cadence, stakeholder intake, measurement) while simultaneously driving a strategic shift. You don’t sacrifice today’s programs to chase tomorrow’s vision.

• Strong technical aptitude — able to internalize complex domains like data modeling, compensation logic, and workflow automation, then make them accessible to non-technical customers.

• Data-informed decision making. You instrument programs, define metrics, and connect enablement activity to business outcomes.

• Exceptional communication. Clear writing and the ability to align cross-functional stakeholders around a vision that may challenge how they’ve previously thought about customer education.

Nice to Have

• Experience designing in-product learning: contextual interventions, embedded guidance, AI-powered help agents.
• Hands-on experience with digital adoption tooling (Pendo, WalkMe, Chameleon, or similar) and a point of view on where these fall short.
• Familiarity with AI content generation workflows — LLMs, AI authoring tools, synthetic video (Synthesia, HeyGen, etc.).

Benefits

• Comprehensive Healthcare: 100% coverage for medical, dental, and vision for all FTEs, with roughly 75% coverage for dependents.
• Flexible Time Off: Flexible vacation days plus quarterly mental health days to ensure you have the space to recharge.
• Annual Stipends: Dedicated funds for your professional development and caretaking needs.
• Work Anniversary Bonuses: Annual bonuses to celebrate your milestones and contributions to the CaptivateIQ team that grow as your tenure does.
• Retirement Savings (US-Only): A 401(k) plan to help you invest in and secure your future.
• Premium Tools: The latest Apple hardware to empower you to do your best work.
• Inclusive Community: Active Employee Resource Groups (ERGs) that celebrate shared identities and support our DEI goals by fostering an environment where diverse talent thrives.

Notice for Prospective Candidates

• Only emails from @captivateiq.com should be trusted.

We are aware of active recruitment scams using the CaptivateIQ name, in which individuals pose as our recruiters and post fake remote job openings and make fake job offers on the Internet. Please note, we will never do the following:

• Attempt to correspond with a candidate using a free web-based account, such as an email address that ends in @gmail.com, @yahoo.com, @hotmail.com, etc.
• Make an offer of employment without conducting multiple rounds of interviews face-to-face using secure video-conferencing technology.
• Ask candidates to cash checks to buy equipment on behalf of CaptivateIQ.
• Ask candidates to make a payment in order to be considered for a position.
• Make early requests for candidates’ personal information such as date of birth, passport details, credit card numbers, bank details and social security number, etc.
• Please note that we’ll only ask for more sensitive personal information in connection with background checks after an offer is made.

$141,000 - $200,000 a year

The salary range represents the minimum and maximum for this position across North America. For candidates in Canada, the range is $193,000–$259,000 CAD. The OTE offered for this position will depend on numerous factors, including individual proficiency, anticipated performance, and the location of the selected candidate. Our OTE is just one component of CaptivateIQ’s competitive total rewards package.

CaptivateIQ participates in E-Verify, web-based system that allows enrolled employers to confirm the eligibility of their employees to work in the United States

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.