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Head of Field Enablement

Remote, United States

About Field Enablement Team

The field enablement team’s mission is to train front line Sales & Service employees to solve problems, to facilitate ongoing internal educational needs to ensure top-notch product supportability, and empower Thumbtack’s customers to to self-serve their needs via public educational content.

To accomplish this mission we focus on:

  • Frontline enablement: lead new hire onboarding for Sales, Service, QA and Trust & Safety teams to expedite ramp time. Perform ongoing training to upskill teams to meet evolving business needs. 
  • Pro and customer education: develop pro and customer education materials to drive pro adoption of Thumbtack products and enable customers to seamlessly find solutions to their questions.  
  • Content: write & edit published educational content across external facing help center, internal facing eLearning materials, and reference knowledge articles.

About the Role

As the Head of Field Enablement, you will play a pivotal role in designing and implementing comprehensive learning strategies to enhance the skills, knowledge, and performance necessary for Thumbtack’s ongoing success. Reporting to the Vice President of Commercial Operations, this is a senior manager level role where you will lead a team that ensures the successful delivery of training programs tailored to meet the needs of our agents, ongoing employee development initiatives, and educational resources for external users. You’ll showcase the success of these programs and initiatives through metrics and attainment of KPIs against company and team goals. Moreover, you will be a key leader within Commercial Operations and expected to partner closely with Sales, Service, Product Operations, QA, Trust & Safety to influence Thumbtack’s commercial direction.


  • Oversee a team of ~20 training specialists and content creators. Motivating teams  through a compelling vision and a clear strategy to deliver value. 
  • Lead group to design & create learning materials, including new hire onboarding curricula, ongoing training, and career development programs including scoping, design, development, delivery, and assessment using a variety of delivery modalities to facilitate the seamless integration of new hires into their roles.
  • Implement systems and processes to evaluate the effectiveness of training initiatives, gather feedback, and improve learning outcomes.
  • Drive process improvements to effectively and efficiently onboard new team members, reduce time to ramp. 
  • Continuously improve sales and service team performance through ongoing training and development. Establish and measure for training impact and adapt procedures to improve operation. 
  • Partner effectively with teams across the company, including Sales Operations, Service Operations, Product Operations, Sales & Service, and Trust & Safety to design a variety of learning solutions to meet business needs from the nuts-and-bolts to the visionary.
  • Serve as a thought leader and advocate for training initiatives, promoting the value of continuous learning as a key driver of individual and organizational success.

What you'll need 

If you don't think you meet all of the criteria below but still are interested in the job, please apply. Nobody checks every box, and we're looking for someone excited to join the team.

  • At least 8 years experience in sales or revenue enablement with emphasis on virtual learning and adult learning concepts using a mix of written, visual, and interactive designs
  • Analytical rigor and strong critical thinking to implement measurement and process to optimize how teams work and partner with stakeholders 
  • Demonstrated ability to manage multiple training and design projects and consult with subject matter experts and key stakeholders
  • Strong coaching, organization and leadership skills to inspire the best in your teams
  • Track record of improving processes that has led lasting, measurable enablement impact 
  • Curiosity and eagerness to learn with demonstrated success in high growth technology companies

Bonus points if you have

  • Experience working in a marketplace business
  • Hands-on experience with virtual training, content development

Thumbtack is a virtual-first company, meaning you can live and work from any one of our approved locations across the United States, Canada or the Philippines.* Learn more about our virtual-first working model here.

For candidates living in San Francisco / Bay Area, New York City, or Seattle metros, the expected salary range for the role is currently $157,500- $193,000. 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.

For candidates living in all other US locations, the expected salary range for this role is currently $133,900 - $164,000 . 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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