Customer Enablement Manager Jobs in Chicago, IL
Customer Enablement Manager jobs in Chicago are concentrated in the Loop, River North, and the Fulton Market District, across enterprise software, financial services, and healthcare technology. Employers hiring right now include PwC, Google, and Mastercard. Find a role that fits below and apply directly.
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Sr. Technical Enablement Architect
The Team + The Role
Pendo tracks AI agent performance, measures adoption, and helps companies prove that their AI investments are working. Selling and delivering that capability requires technical depth across product, integrations, APIs, data models, agent instrumentation, and real enterprise environments. The enablement team builds that depth for the customer-facing roles responsible for bringing Pendo's product value to market.
As Principal Technical Enablement Architect, you are the technical authority on the enablement team. You define what technical fluency looks like across AEs, ADs, and CEs, translate product launches into field-ready technical standards, and build the hands-on content, frameworks, and feedback loops that help the field engage customers credibly. This is a senior, ambiguous role that requires judgment with incomplete information, influence without authority, and accountability to measurable revenue impact.
This is a remote role based in the United States.
What this looks like day-to-day
- Define technical depth standards: Establish what technical fluency looks like for AEs, ADs, and CEs across the buyer journey, from discovery through expansion. You will set differentiated thresholds by role while maintaining one coherent framework that enablement leads can build toward.
- Translate product launches technically: Partner with the GTM Readiness Lead on every launch, with readiness owning messaging and value translation while you own technical depth translation. You will anticipate how new capabilities, especially AI and agent features, will behave in real customer environments before they appear in field conversations.
- Own the technical content library: Build and maintain hands-on technical enablement content, including sandbox environments, integration walkthroughs, API usage guides, and architecture scenarios. You will keep content current, document recurring technical blockers, and bring those insights back to enablement and product teams.
- Measure enablement impact: Use sales metrics, pipeline data, field performance analytics, adoption metrics, readiness scores, and post-training performance data to determine which enablement strategies are working. You will iterate on effective programs, retire what does not work, and connect enablement outcomes to pipeline velocity, technical win rates, deal cycle compression, and revenue impact.
- Calibrate AI call scoring: Partner with the GTM AI team to ensure AI call scoring captures technical quality, not only process compliance. You will define what strong technical depth sounds like in customer-facing conversations precisely enough for AI-based scoring to evaluate it.
- Partner across GTM and Product: Collaborate with Marketing, Sales Operations, and Product Management to align technical enablement content with campaigns, messaging, operational workflows, and roadmap direction. You will surface field-level technical insights and customer environment patterns that help enablement stay ahead of the product roadmap.
- Engage with customers when needed: Participate in strategic pre-sale and post-sale technical interactions, including product demonstrations, technical presentations, proof-of-concept builds, and solution validation. You will use direct customer engagement to pressure-test enablement standards, provide follow-up technical support, and share best practices with the field.
Who You Are
Beyond the qualifications, we hire through a specific lens. These aren't buzzwords; they're the things we'll actually look for in how you talk about your work.
You're a builder, not a maintainer.
You're most energized when there isn't a clear path yet, and you get to define it. You don't wait for direction; you identify gaps, shape solutions, and drive them forward. At Pendo, great Principal Technical Enablement Architects don't just follow instructions; they operate as strategic advisors, influencing decisions, guiding stakeholders, and elevating how we work.
You're AI-curious - genuinely.
You're not using AI tools occasionally. You're rewiring how you work around them. You're faster, sharper, and more prolific because of it, and you bring that energy to everything — how you approach your work, how you prep, how you communicate, how you think. We want someone who sees AI as a multiplier, not a shortcut.
Must-haves
- 10+ years in solutions or sales engineering, forward-deployed engineering, or senior technical account management, with deep hands-on product experience in enterprise software environments.
- Deep knowledge of Pendo or a directly comparable platform, including configuration, integrations, APIs, and data architecture.
- Ability to build and review integrations using HTML, CSS, JavaScript, and REST APIs, not just explain technical concepts at a high level.
- Experience designing technical training programs that make complex product, integration, and architecture concepts teachable without oversimplifying them.
- Strong understanding of enterprise technical environments and how products operate in real customer architectures, edge cases, and implementation contexts.
- Routine use of AI tools as part of your own workflow, with the expectation that AI fluency is a baseline part of how you work.
- Demonstrated ability to use sales metrics and field performance data to evaluate enablement effectiveness and quantify the impact of training on pipeline and revenue outcomes.
- Experience collaborating cross-functionally with Marketing, Sales Operations, and Product Management in a GTM organization.
- Fluency in buyer behavior and the enterprise buying process, including how technical evaluation maps to purchasing decisions.
Nice-to-haves
- Direct Pendo experience, particularly with Agent Analytics or AI-native product instrumentation.
- Experience as a forward-deployed engineer or in a premium embedded technical role at an enterprise software company.
- Background in integration architecture, data modeling, or AI and agent instrumentation.
- Experience setting technical standards across multiple role levels in a GTM organization.
- Experience providing pre-sale technical support, including product demonstrations, rapid prototyping, or proof-of-concept development for enterprise customers.
About Pendo
Pendo was founded in 2013 by former product managers, who combined their heads and hearts to build something they wanted but never had as product managers: a simple way to understand and attack what truly drives product success. Our mission is to improve society's experience with software. Come join one of the fastest-growing startups, supported by best-in-class institutions like Battery Ventures, Salesforce Ventures, Spark Capital and Meritech.
Pendo Core Values: Bias to Act, Hone Your Craft, The Team is Pendo, and Maniacal Focus.
Location: Pendo is a hybrid culture. In-office 3 days per week unless designated remote.
Compensation: The expected salary range for this role to be performed in USA is $178,600 - $214,000.
Benefits: Pendo offers highly competitive, employer-heavy coverage in the United States, including $0 premium options, strong 401(k) match, equity, and flexible time off.
EEOC: We are an equal opportunity employer and believe having diverse teams where everyone brings their whole self to Pendo is key to our success. We welcome all people of different backgrounds, experiences, abilities and perspectives.
Accessibility: Pendo is committed to working with, and providing access and reasonable accommodation to, applicants with mental and/or physical disabilities. If you think you may require an accommodation for any part of the recruitment process, please send a request to: accommodation@pendo.io. All requests for accommodations are treated discreetly and confidentially, as practical and permitted by law.
See All 25 Customer Enablement Manager Jobs in Chicago
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Find JobsCustomer Enablement Manager Job Market in Chicago
Who's Hiring
- PwC3

- Google3

- Mastercard2

- Huron Consulting2

- WTW1

Top Industries Hiring
- Technology & Software8
- Banking & Financial Services5
- Consulting & Professional Services5
- Fintech3
- Artificial Intelligence3
Customer Enablement Manager Jobs in Chicago: Frequently Asked Questions
How do I get a customer enablement manager job in Chicago?
The strongest path is targeting Chicago's dense cluster of enterprise software and SaaS companies in the Loop and Fulton Market District, along with financial services firms and health tech employers on the North Side. Candidates who combine onboarding or implementation experience with measurable retention or expansion outcomes stand out. Familiarity with tools like Salesforce, Gainsight, or Chorus is a consistent advantage in Chicago's market.
Which companies hire customer enablement managers in Chicago?
Chicago customer enablement manager roles are posted by PwC, Google, and Mastercard and others right now, based on current listings on Migrate Mate as of June 2026. Chicago's mix of legacy enterprises, mid-market SaaS firms, and fast-growing fintech and health tech companies creates consistent demand for this role across a wide range of employer sizes.
Are there remote customer enablement manager jobs in Chicago?
Yes, though availability depends on the role: customer enablement work tied to live training, onsite implementation, or in-person customer success tends to require at least some presence, while content development, digital onboarding, and scaled enablement roles are more frequently remote. About 50% of customer enablement manager openings tied to Chicago are remote or hybrid as of June 2026, with hybrid arrangements most common among Chicago's enterprise software and financial services employers.
How can I get a customer enablement manager job in Chicago with little or no experience?
The most realistic entry path is moving from a customer success associate, implementation coordinator, or technical support role at one of Chicago's many mid-market SaaS or fintech companies, where internal mobility into enablement is common. Chicago employers in healthcare technology and professional services also hire for enablement coordinators who build toward the manager level. Building a portfolio of onboarding materials or training content, even from a previous role, gives candidates a concrete edge.
Which industries hire the most customer enablement managers in Chicago?
Chicago customer enablement manager roles concentrate in Technology & Software, Banking & Financial Services, and Consulting & Professional Services, based on current listings on Migrate Mate as of June 2026. Chicago's position as a hub for enterprise software, financial technology, and large healthcare systems creates sustained demand for professionals who can drive product adoption and customer outcomes at scale.
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