Sales Enablement Manager Jobs in Chicago, IL
Sales Enablement Manager jobs in Chicago are concentrated in the Loop, River North, and Fulton Market, driven by demand from B2B SaaS, financial services, and healthcare technology companies. 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.
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Who's Hiring
- PwC3

- Google3

- Mastercard2

- Huron Consulting2

- WTW1

Top Industries Hiring
- Technology & Software8
- Banking & Financial Services5
- Consulting & Professional Services5
- Fintech3
- Artificial Intelligence3
Sales Enablement Manager Jobs in Chicago: Frequently Asked Questions
How do I get a sales enablement manager job in Chicago?
Focus your search on the Loop and River North, where B2B software, fintech, and healthcare technology companies cluster their sales organizations. Candidates who can demonstrate measurable impact on sales productivity, such as ramp-time reduction or playbook adoption rates, stand out in Chicago's competitive market. Experience with Salesforce, Highspot, or Seismic is consistently valued by local enterprise employers.
Which companies hire sales enablement managers in Chicago?
Companies currently hiring sales enablement managers in Chicago include PwC, Google, and Mastercard, per current listings on Migrate Mate as of June 2026. Chicago's mix of legacy enterprise firms, fast-growing SaaS startups in Fulton Market, and large financial institutions means openings exist across a wide range of company sizes and sales models.
Are there remote sales enablement manager jobs in Chicago?
Yes, sales enablement manager roles are well-suited to remote and hybrid arrangements because the core work, such as content development, LMS administration, and program design, is largely screen-based. About 50% of sales enablement manager openings tied to Chicago are remote or hybrid as of June 2026. Coaching and onsite sales coaching components are most likely to require in-person presence at Chicago offices.
How can I get a sales enablement manager job in Chicago with little or no experience?
The most realistic entry path in Chicago is moving laterally from a sales development or account executive role into a sales enablement specialist or coordinator position. Mid-market SaaS companies in Fulton Market and River North regularly hire junior enablement staff from within their own sales teams. Building a portfolio of sales playbooks, onboarding materials, or training decks gives candidates a concrete edge over applicants with only job titles to show.
Which industries hire the most sales enablement managers in Chicago?
The sectors hiring the most sales enablement managers in Chicago are Technology & Software, Banking & Financial Services, and Consulting & Professional Services, based on current listings on Migrate Mate as of June 2026. Chicago's dense concentration of enterprise software vendors, financial services firms, and health tech companies creates sustained demand for enablement professionals who can support large, quota-carrying sales teams.
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