Technical Director Jobs in Chicago, IL
Technical Director jobs in Chicago are in active demand, concentrated in the Loop, River North, and the Fulton Market corridor across technology, media, and professional services. Employers hiring right now include Huron Consulting, PwC, and Salesforce. Scan the live roles below and apply to whichever ones fit.
Find Technical Director JobsOverview
Showing 5 of 50+ Technical Director jobs
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
The Opportunity
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.
Responsibilities
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.
Required Qualifications
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.
#LI-onsite
P25402
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 Okta Experience
- Supporting Your Well-Being
- Driving Social Impact
- Developing Talent and Fostering Connection + Community
We are intentional about connection. Our global community, spanning over 20 offices worldwide, is united by a drive to innovate. Your journey begins with an immersive, in-person onboarding experience designed to accelerate your impact and connect you to our mission and team from day one.
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
Okta is the leading independent provider of identity for the enterprise. The Okta Identity Cloud enables organizations to securely connect the right people to the right technologies at the right time. With over 7,000 pre-built integrations to applications and infrastructure providers, Okta customers can easily and securely use the best technologies for their business. More than 19,300 organizations, including JetBlue, Nordstrom, Slack, T-Mobile, Takeda, Teach for America, and Twilio, trust Okta to help protect the identities of their workforces and customers.
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
The Opportunity
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.
Responsibilities
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.
Required Qualifications
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.
#LI-onsite
P25402
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 Okta Experience
- Supporting Your Well-Being
- Driving Social Impact
- Developing Talent and Fostering Connection + Community
We are intentional about connection. Our global community, spanning over 20 offices worldwide, is united by a drive to innovate. Your journey begins with an immersive, in-person onboarding experience designed to accelerate your impact and connect you to our mission and team from day one.
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
Okta is the leading independent provider of identity for the enterprise. The Okta Identity Cloud enables organizations to securely connect the right people to the right technologies at the right time. With over 7,000 pre-built integrations to applications and infrastructure providers, Okta customers can easily and securely use the best technologies for their business. More than 19,300 organizations, including JetBlue, Nordstrom, Slack, T-Mobile, Takeda, Teach for America, and Twilio, trust Okta to help protect the identities of their workforces and customers.
See All 50 Technical Director Jobs in Chicago
Find roles in Chicago that match your experience and apply in just a few clicks.
Find Technical Director JobsTechnical Director Job Market in Chicago
Who's Hiring
- Huron Consulting6
- PwC3
- Salesforce3
- Meta2
- Stripe2
Top Industries Hiring
- Technology & Software12
- Consulting & Professional Services9
- Insurance4
- Banking & Financial Services4
- Investment & Asset Management4
Technical Director Jobs in Chicago: Frequently Asked Questions
How do I get a technical director job in Chicago?
Target Chicago's strongest hiring sectors: enterprise technology, advertising and media agencies in River North, financial services firms in the Loop, and healthtech companies in the Fulton Market district. Candidates who stand out combine deep technical expertise with demonstrated leadership over cross-functional teams. Building a portfolio of Chicago-area projects and connecting with the local tech community through meetups and industry events gives you a measurable edge over remote applicants.
Which companies hire technical directors in Chicago?
Companies currently hiring technical directors in Chicago include Huron Consulting, PwC, and Salesforce, per current listings on Migrate Mate as of June 2026. Chicago's market draws a wide mix of employers, from global Fortune 500 headquarters and major financial institutions in the Loop to fast-growing startups and creative agencies concentrated in Fulton Market and River North.
Are there remote technical director jobs in Chicago?
Yes, though remote availability depends heavily on the role. Technical directors overseeing infrastructure, software architecture, or digital strategy tend to have the most remote flexibility, while those managing studios, broadcast operations, or physical production are typically required on-site. About 34% of technical director openings tied to Chicago are remote or hybrid as of June 2026, with hybrid arrangements most common at technology and professional services firms headquartered in the Loop.
How can I get a technical director job in Chicago with little or no experience?
The most realistic entry path is moving up from a senior individual contributor role, such as senior engineer, lead developer, or senior producer, at a Chicago employer that promotes from within. Mid-size technology firms and advertising agencies in River North and Fulton Market frequently hire strong senior contributors before elevating them into director-level roles. Building internal visibility through cross-team projects and mentoring junior staff makes that transition faster at most Chicago employers.
Which industries hire the most technical directors in Chicago?
Chicago technical director roles concentrate in Technology & Software, Consulting & Professional Services, and Insurance, based on current listings on Migrate Mate as of June 2026. Chicago's position as a hub for financial services, enterprise software, and a historically strong advertising and media industry creates sustained demand for technical directors who can bridge creative and engineering teams or oversee large-scale infrastructure.
See All 50 Technical Director Jobs in Chicago
Find roles in Chicago that match your experience and apply in just a few clicks.
Find Technical Director Jobs