Sr. Director, Technical Development and Delivery

Okta•Chicago, IL

7d•$206,000 - $350,900•Hybrid

About The Position

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.

Requirements

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.
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.
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 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.
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.
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.
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.
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.