Technical Development Manager Jobs in Chicago, IL

Secure Every Identity, from AI to Human Identity is the key to unlocking the potential of AI. Okta secures AI by building the trusted, neutral infrastructure that enables organizations to safely embrace this new era. This work requires a relentless drive to solve complex challenges with real-world stakes. We are looking for builders and owners who operate with speed and urgency and execute with excellence. This is an opportunity to do career-defining work. We're all in on this mission. If you are too, let's talk.

Chicago, IL or San Francisco, CA

Hybrid- Onsite 2 days per week

We are looking for a strategic, data-driven Sr. Director, Technical Development and Delivery to create and lead our AI-driven technical enablement content strategy and delivery as well as own functional delivery through our pre-sales, partner and onboarding enablement teams.

This leader will own the full enablement content lifecycle to help drive technical acumen across all CRO audiences while measuring impact and driving change. This is a highly cross-functional role that sits at the intersection of sales, product, marketing, partners and technology.

The right candidate brings deep experience in creating and executing strategy - both immediate and in service of long-range planning. If you have a passion for enabling technical audiences, a sophisticated approach to content optimization, a bias for action, and a clear point of view on how AI is reshaping the enablement discipline, we’d love to meet you.

Team Leadership & Organizational Development

• Create short-term and long range enablement plans that align to driving business outcomes for the CRO organization.
• Set strategic priorities across the team, aligning individual work streams to overarching revenue and company goals.
• Lead, develop, and grow a team of technical enablement professionals and leaders
• Coach and develop managers and individual contributors, building a high-performance culture with clear career progression.
• Serve as a trusted advisor to field leadership, our partner team and product - translating business challenges into enablement solutions with measurable outcomes.

Technical Enablement Program Delivery

• Act as a strategic advisor on enablement that drives impact to both the Presales and External Partner organizations, providing data-driven recommendations and support to accelerate technical outcomes
• Build and scale enablement programs purpose-built for technical sales roles including Sales Engineers and Partners.
• Develop deep product fluency programs that enable technical audiences to confidently articulate complex identity and security concepts, competitive differentiators, and the technical value proposition of Okta.
• Partner with Product and Engineering to translate Okta's platform capabilities into field-ready training, certifications, and enablement content.

Elevating Technical Fluency Across All Revenue Audiences

• Own and drive a cross-functional strategy to raise the technical competency floor across every customer-facing role in the CRO organization
• Design tiered technical fluency frameworks that define what \"good\" looks like at each role, with clear progression paths from foundational product knowledge to advanced identity and security domain expertise.
• Build structured learning programs that help commercial sellers understand the technical landscape their buyers operate in, including modern identity protocols (OIDC, SAML), Zero Trust architecture, compliance frameworks, threat vectors, and cloud security fundamentals so they can lead with credibility.
• Create role-based certification programs with measurable competency assessments that reinforce technical knowledge retention over time.
• Champion a culture of continuous technical learning, including speaker series with engineers and product leaders, competitive deep-dives, and hands-on product lab experiences.

Content Strategy & Optimization

• Own the strategy and quality bar for all revenue-facing content and ensure it is optimized for AI discoverability and use.
• Help implement and optimize an enablement content platform to drive measurable increases in seller engagement and content utilization.
• Leverage data and analytics to identify content gaps, measure content effectiveness, and continuously improve what gets used and what wins deals.

AI Strategy & Innovation

• Help define and lead the organization's content creation for our AI driven enablement strategy.
• Evaluate and implement AI-native enablement tooling, piloting new capabilities and building adoption programs that drive efficiency gains.
• Stay ahead of the market on how AI is reshaping the buyer and seller experience in enterprise security and identity.

Experience & Leadership

• 12+ years of progressive experience in sales enablement, field enablement, or product marketing, with at least 5 years in a senior leadership role managing multi-functional teams.
• Proven ability to lead, develop, and retain high-performing teams across multiple functions and geographies.
• Experience serving as a strategic partner to CRO or VP-level revenue and technical leaders.

Technical Enablement Expertise

• A clear, articulated philosophy and proven track record for elevating technical credibility across non-technical seller audiences.
• Comfort operating in a security domain environment; ability to develop deep fluency in identity and access management (IAM), compliance, and threat detection.
• Direct experience in the security or identity industry is strongly preferred.

Content & AI Strategy

• Experience owning a content strategy for a complex, technical product portfolio with a fast-moving roadmap.
• Strong fluency in AI tools with a clear perspective on how to embed AI into enablement and field productivity programs.
• Demonstrated ability to evaluate, implement, and drive adoption of AI-native or AI-enhanced enablement tooling.

Tools & Methodology

• Hands-on experience with enablement platforms (e.g., Highspot, Seismic), and revenue tools including Salesforce and Gong.
• Deep familiarity with sales methodologies such as MEDDPICC, Command of the Message, or Challenger Sale.
• Experience building and interpreting enablement performance dashboards in partnership with Revenue Operations.

Communication & Influence

• Exceptional communication and storytelling skills.
• Strong cross-functional collaboration skills with a history of aligning Sales, Product Marketing, and Product Management.

• Supporting Your Well-Being
• Driving Social Impact
• Developing Talent and Fostering Connection + Community

The annual base salary range for this position for candidates located in the San Francisco Bay area is between:

$255,000 — $350,900 USD

Below is the annual base salary range for candidates located in California (excluding San Francisco Bay Area), Colorado, Illinois, New York and Washington. Your actual base salary will depend on factors such as your skills, qualifications, experience, and work location. In addition, Okta offers equity (where applicable), bonus, and benefits, including health, dental and vision insurance, 401(k), flexible spending account, and paid leave (including PTO and parental leave) in accordance with our applicable plans and policies. To learn more about our Total Rewards program please visit: https://rewards.okta.com/us.

The annual base salary range for this position for candidates located in California (excluding San Francisco Bay Area), Colorado, Illinois, New York and Washington is between:

$206,000 — $282,700 USD

Okta is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, ancestry, marital status, age, physical or mental disability, or status as a protected veteran. We also consider for employment qualified applicants with arrest and convictions records, consistent with applicable laws. If reasonable accommodation is needed to complete any part of the job application, interview process, or onboarding please use this Form to request an accommodation. Notice for New York City Applicants & Employees: Okta may use Automated Employment Decision Tools (AEDT), as defined by New York City Local Law 144, that use artificial intelligence, machine learning, or other automated processes to assist in our recruitment and hiring process. In accordance with NYC Local Law 144, if you are an applicant or employee residing in New York City, please click here to view our full NYC AEDT Notice.