Sr. Director, Technical Development and Delivery

Okta•Chicago, IL

6d•Hybrid

About The Position

Okta is seeking a strategic, data-driven Sr. Director, Technical Development and Delivery to create and lead their AI-driven technical enablement content strategy and delivery. This role will also own functional delivery through pre-sales, partner, and onboarding enablement teams. The individual will manage the entire enablement content lifecycle to enhance technical acumen across all CRO audiences, measuring impact and driving change. This is a highly cross-functional position at the intersection of sales, product, marketing, partners, and technology, requiring expertise in strategy creation and execution, both immediate and long-term. The ideal candidate is passionate about enabling technical audiences, employs a sophisticated approach to content optimization, demonstrates a bias for action, and has a clear perspective on AI's impact on enablement.

Requirements

12+ years of progressive experience in sales enablement, field enablement, or product marketing.
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.
A clear 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.
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.
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.
Exceptional communication and storytelling skills.
Strong cross-functional collaboration skills with a history of aligning Sales, Product Marketing, and Product Management.

Nice To Haves

Direct experience in the security or identity industry is strongly preferred.

Responsibilities

Create short-term and long-range enablement plans aligned with CRO organization business outcomes.
Set strategic priorities for the team, aligning individual work streams with overarching revenue and company goals.
Lead, develop, and grow a team of technical enablement professionals and leaders.
Coach and develop managers and individual contributors, fostering a high-performance culture with clear career progression.
Serve as a trusted advisor to field leadership, the partner team, and product, translating business challenges into enablement solutions with measurable outcomes.
Act as a strategic advisor on enablement to drive impact for both Presales and External Partner organizations, providing data-driven recommendations and support.
Build and scale enablement programs specifically for technical sales roles, including Sales Engineers and Partners.
Develop deep product fluency programs enabling technical audiences to articulate Okta's platform capabilities, competitive differentiators, and technical value proposition.
Partner with Product and Engineering to translate platform capabilities into field-ready training, certifications, and enablement content.
Own and drive a cross-functional strategy to elevate technical competency across all customer-facing roles in the CRO organization.
Design tiered technical fluency frameworks defining 'good' at each role with clear progression paths.
Build structured learning programs for commercial sellers on the technical landscape, including modern identity protocols, Zero Trust architecture, compliance frameworks, threat vectors, and cloud security fundamentals.
Create role-based certification programs with measurable competency assessments.
Champion a culture of continuous technical learning through speaker series, competitive deep-dives, and hands-on product lab experiences.
Own the strategy and quality bar for all revenue-facing content, ensuring optimization for AI discoverability and use.
Help implement and optimize an enablement content platform to increase seller engagement and content utilization.
Leverage data and analytics to identify content gaps, measure content effectiveness, and improve content.
Define and lead the organization's content creation for an AI-driven enablement strategy.
Evaluate and implement AI-native enablement tooling, piloting new capabilities and building adoption programs.
Stay informed about AI's impact on the buyer and seller experience in enterprise security and identity.