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About the Field Enablement Team

The Field Enablement team at Thumbtack empowers our employees, pros, and customers through impactful learning experiences that drive performance, skill development, and business outcomes. We’re a collaborative, cross-functional team made up of three key pillars: Enablement Design, Enablement Delivery, and Content & Communications. Together, we identify learning needs across the organization and create thoughtful, scalable solutions that support every stage of the employee lifecycle. From onboarding to ongoing development, our work is deeply embedded in the success of Thumbtack’s frontline teams and plays a vital role in ensuring a consistent, high-quality experience for the pros and customers who rely on us every day.

About the Role

We’re seeking a strategic leader to manage our Enablement Delivery team. As the Manager II of Enablement Delivery, you will lead the delivery engine that powers performance across Thumbtack’s frontline organizations — including Sales, Service, Success, and Trust & Safety.

While this role manages a team of trainers and facilitators, the scope extends well beyond execution. You will own the delivery strategy across onboarding and continuous learning programs, ensuring our learning experiences drive measurable improvements in key frontline performance metrics, such as time to productivity, training ROI, and other indicators of business impact.

You will operate as a peer partner to the Enablement Design leader, shaping modality decisions and ensuring programs are architected for scalable, high-impact delivery. In parallel, you will partner with senior business leaders to translate evolving company priorities into performance-focused enablement strategies.

This leader will elevate how delivery operates — building scalable systems, modernizing workflows, and embedding AI-enabled practices into both training experiences and team operations. Success in this role requires strong people leadership, operational rigor, business acumen, and a forward-looking mindset about how technology and AI can accelerate frontline performance

What you'll do

• Lead, coach, and develop a high-performing team of enablement trainers and facilitators, establishing clear performance standards, quality benchmarks, and scalable coaching frameworks.
• Own the end-to-end delivery strategy for onboarding and continuous learning across all frontline organizations, ensuring alignment to company priorities and measurable business outcomes.
• Partner closely with the Enablement Design team to shape learning strategies, influence modality decisions (live, virtual, blended, AI-enabled), and ensure programs are architected for scalable, high-impact delivery.
• Build and operationalize scalable delivery systems, including capacity models, prioritization frameworks, facilitator readiness standards, and operating rhythms that enable consistent execution at scale.
• Partner with senior leaders across Sales, Service, Success, Trust & Safety, and Commercial Ops to identify performance gaps and drive enablement solutions tied to time to productivity, ramp time, and training ROI.
• Define, measure, and continuously improve delivery impact metrics, using data to refine programs, reallocate resources, and communicate ROI and tradeoffs to leadership.
• Champion AI-enabled delivery by embedding AI tools and workflows into both team operations and learning experiences, increasing efficiency, personalization, and speed to impact.
• Serve as a player-coach by facilitating high-impact sessions as needed, modeling advanced facilitation, business-context integration, and the standard of excellence expected across the delivery organization.

In order to be successful, you must bring

• 6+ years of experience in enablement, learning & development, or a related performance-focused function, including experience operating at scale across multiple business functions.
• 3+ years of people management experience with a demonstrated track record of building high-performing teams, raising performance standards, and developing emerging leaders.
• Proven experience owning or significantly influencing enablement strategy tied to measurable business outcomes such as time to productivity, ramp time, revenue performance, quality, or efficiency metrics.
• Experience partnering with senior leaders (Director level and above) to translate business priorities into performance-driven enablement plans.
• Strong operational and systems-thinking capabilities, including experience designing scalable processes, capacity planning models, and delivery operating rhythms.
• Demonstrated ability to use data and insights to evaluate program effectiveness, communicate ROI, and make prioritization tradeoffs.
• Fluency with AI tools and emerging technologies, with experience integrating AI into team workflows or learning programs to increase efficiency and impact

Expected salary ranges

• For candidates living in San Francisco / Bay Area, San Jose, New York City, or Seattle metros, the expected salary range for the role is currently $114,000 - $147,000.
• For candidates living in Austin, TX or Washington DC metros or in California, Massachusetts, New Jersey, or Washington states, the expected salary range for the role is currently $103,000 - $133,000.
• For candidates living in all other US locations, the expected salary range for this role is currently $97,000 - $125,000.

Actual offered salaries will vary and will be based on various factors, such as calibrated job level, qualifications, skills, competencies, and proficiency for the role.

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