Director, Sales Strategy & Operations

Thumbtack helps millions of people confidently care for their homes.

Thumbtack is the one app you need to take care of and improve your home - from personalized guidance to AI tools and a best-in-class hiring experience. Every day in every county of the U.S., people turn to Thumbtack to complete urgent repairs, seasonal maintenance and bigger improvements. We help homeowners know which projects to do, when to do them and who to hire from our growing community of 300,000 local service businesses. If making an impact inspires you, join us. Imagine what we’ll build together.

About the Sales Operations Team

The Sales Operations team helps Thumbtack’s sales and account management teams grow revenue. We build the programs and tools that help reps bring local service businesses onto Thumbtack and grow strategic existing accounts. The work spans acquisition and account management, with close partners in Product, Marketing, Data Science, Enablement, and QA.

About the role

You’ll drive Thumbtack’s sales strategy and partner closely with the Sales leadership team to execute it. Your focus is growing sales revenue by bringing more pros onto Thumbtack and expanding relationships with existing accounts.

Reporting to the Vice President of Commercial Operations, you’ll lead analysts and managers across North America and the Philippines. There’s room to build new approaches to outbound prospecting, account expansion, and the use of AI in sales. You’ll get close to the data and frontline work yourself, then turn what you learn into programs and strategic levers that’ll deliver impact.

What you’ll do

• Drive the sales strategy to grow revenue, partnering closely with Sales leadership to set priorities and execute against shared goals.
• Build new approaches to outbound acquisition and existing account expansion. Test them in the field and scale what works.
• Get into the data and spend time with reps and pros to understand where there’s opportunities to maximize sales and pro lifetime value. Turn those findings into changes that improve conversion and account growth.
• Use AI to build better prospecting, selling, and account management workflows. Measure whether reps use them and whether they increase revenue or productivity.
• Get agreement on priorities and ownership with Product, Marketing, Data Science, and sales technology partners. Resolve dependencies that hold up execution.
• Keep core sales operations running well, including lead routing, account management workflows, and sales tools, so reps can spend more time selling.
• Develop the managers on your team and give them clear ownership. Make hiring and performance decisions that build the team’s ability to deliver.

In order to be successful, you must bring

• Experience developing and executing sales or commercial strategy, with clear evidence of revenue growth. High-volume sales to small businesses is especially relevant; management consulting experience is a plus.
• The analytical depth to investigate a problem yourself. You question metric definitions, check the underlying data, and test whether your diagnosis holds up.
• Experience building a new sales motion, team, or operating capability from an unclear starting point. You’ve done the work to get it adopted and can show what impact that created.
• Experience leading managers and developing people. You set clear expectations, give direct feedback, and make difficult decisions when the team needs them.
• Clear communication and sound judgment with partners. You can challenge a senior stakeholder’s assumptions with data and evidence, understand your partner’s differing view and drive impact with speed.
• Curiosity and urgency. You learn unfamiliar areas quickly and are willing to try a different approach. You can make a call with imperfect information and adjust as you learn.

Expected salary ranges

• For candidates living in Ontario and British Columbia, the expected total cash compensation (base salary + variable pay, if applicable) range for this role is currently $183,600 - $237,600

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.

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: recruitingops@thumbtack.com .

For information about how Thumbtack collects, uses, and shares personal information about job applicants, please see our Job Applicant Privacy Policy .

We put as much craftsmanship into candidate safety as we do into the hiring experience itself. While scammers may try to impersonate our team, we’ll never ask you for money, banking info, or SSNs during hiring. Check out our blueprint on how to spot the fakes.

Where you can sell from

Fully remote, for people based in Canada.