Enablement Trainer II

About the Field Enablement Team

The Field Enablement team’s mission is to enable our frontline Experience Operations (Sales, Service, Success, and Trust & Safety) employees to solve problems, facilitate ongoing internal educational programs to ensure top-notch product supportability, and empower Thumbtack’s customers and pros to self-serve their needs via public educational content.

About the Role

As an Enablement Trainer II, you will play a critical role in delivering and evolving high-impact training programs that enable our frontline teams to perform at their best. You will serve as a trusted facilitator and subject matter expert, leading complex training initiatives across Sales, Service, Success, Trust & Safety, and partner-facing audiences.

In this role, you will own the facilitation of major enablement programs such as employee onboarding, continuous upskilling initiatives, and virtual learning experiences for Thumbtack Pros, customers, and key partners. You will partner closely with Enablement Design, Product Operations, and cross-functional stakeholders to ensure training experiences are engaging, relevant, and aligned to business priorities.

You will also help pilot new training approaches, contribute to program iteration and improvement, and provide coaching and mentorship to fellow trainers. Your work will directly impact performance outcomes, customer experience, and the growth and development of Thumbtack employees.

What you'll do

• Advanced Training Facilitation: Lead high-impact, interactive training sessions for diverse and often tenured audiences, modeling best-in-class facilitation techniques and fostering meaningful knowledge transfer.
• Program Ownership: Own the delivery and execution of core enablement programs such as onboarding, role-based upskilling, and large-scale learning initiatives, ensuring consistency, quality, and strong learner engagement.
• Continuous Learning Enablement: Facilitate ongoing training initiatives that address evolving product capabilities, industry trends, performance gaps, and leadership or soft-skill development needs.
• Program Evaluation & Iteration: Assess training effectiveness using learner feedback, performance metrics, and business outcomes; partner with Enablement Design to continuously improve content and delivery methods.
• Cross-Functional Collaboration: Partner closely with Enablement Design, Product Operations, Partnerships, and frontline leaders to align training initiatives with operational goals and strategic priorities.
• Expanded Audience Enablement: Deliver training for Thumbtack Pros, customers, key partners, and internal partner-facing teams to drive adoption, confidence, and satisfaction across the ecosystem.
• Mentorship & Innovation: Support and mentor junior trainers while piloting new facilitation techniques or learning approaches that raise the bar for enablement delivery.

In order to be successful, you must bring

• Educational Background: A bachelor’s degree in business, education, organizational development, or a related field is preferred, or an equivalent combination of education and experience.
• 5–7+ years of experience in training, enablement, or a related role, preferably supporting sales, service, success, or partner-facing teams.
• Advanced facilitation skills, with demonstrated ability to lead complex, high-stakes virtual training sessions and adapt approaches for different audiences and learning needs.
• Exceptional verbal and written communication skills, with the ability to influence, engage, and inspire learners.  
• Strong stakeholder partnership skills and experience collaborating cross-functionally to deliver aligned enablement outcomes.
• Ability to connect training initiatives to performance improvement and business impact, using feedback and metrics to inform iteration.
• A growth mindset and strong team-player mentality, demonstrating adaptability, ownership, and a commitment to continuous learning and development.

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 $79,000 - $102,000.
• 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 $71,000 - $92,000.
• For candidates living in all other US locations, the expected salary range for this role is currently $67,000 - $87,000.

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.