Remote job description

A home is the biggest investment most people make, and yet, it doesn't come with a manual. That's why we're building the only app homeowners need to effortlessly manage their homes ?" knowing what to do, when to do it, and who to hire. With Thumbtack, millions of people care for what matters most, and pros earn billions of dollars through our platform. And as one of the fastest-growing companies in a $600B+ industry ?" we must be doing something right.

We are driven by a common goal and the deep satisfaction that comes from knowing our work supports local economies, helps small businesses grow, and brings homeowners peace of mind. We're seeking people who continually put our purpose first: advocating for pros and customers, embracing change, and choosing teamwork every day.

At Thumbtack, we're creating a new era of home care. If making an impact and the chance to do good inspires you, join us. Imagine what we'll build together.

Thumbtack by the Numbers

  • Available nationwide in every U.S. county
  • 80 million projects started on Thumbtack
  • 10 million 5-star reviews and counting
  • Pros earn billions on our platform
  • 1000+ employees
  • $3.2 billion valuation (June, 2021)

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.


Benefits & Perks
  • Virtual-first working model coupled with in-person events
  • 20 company-wide holidays including a week-long end-of-year company shutdown
  • Libraries (optional use collaboration & connection hubs) in San Francisco and Salt Lake City
  • WiFi reimbursements
  • Cell phone reimbursements (North America)
  • Employee Assistance Program for mental health and well-being

Learn More About Us

Thumbtack embraces diversity. We are proud to be an equal opportunity workplace and do not discriminate on the basis of sex, race, color, age, pregnancy, sexual orientation, gender identity or expression, religion, national origin, ancestry, citizenship, marital status, military or veteran status, genetic information, disability status, or any other characteristic protected by federal, provincial, state, or local law. We also will consider for employment qualified applicants with arrest and conviction records, consistent with applicable law.

Thumbtack is committed to working with and providing reasonable accommodation to individuals with disabilities. If you would like to request a reasonable accommodation for a medical condition or disability during any part of the application process, please contact:

If you are a California resident, please review information regarding your rights under California privacy laws contained in Thumbtack's Privacy policy available at .

Company name: Thumbtack
Remote job title: Head of Field Enablement
Job tags: Field Enablement, Content Development, Enablement

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