Director, Sales Operations Virtual, Ontario Commercial Operations

Thumbtack; Canada; Remote; CAD 184,000 - 238,000; Full time

Benefits offered by this job

Paid time off

Remote work stipend

Professional development stipend

Parental leave

Thumbtack Bucks

Annual wellness stipend

Job summary

Thumbtack is seeking a strategic Sales Operations leader to drive revenue growth across North America and the Philippines, collaborating with Sales leadership to set priorities and scale outbound and account expansion. The role emphasizes leveraging AI in prospecting and sales workflows.

You will lead analysts and managers, partner with Product, Marketing, Data Science, and sales tech to deliver data-driven programs that improve conversion and lifetime value across accounts.

Qualifications

• Experience developing and executing sales or commercial strategy with revenue growth.

Responsibilities

• Drive the sales strategy to grow revenue, partnering with Sales leadership to set priorities and execute against shared goals.

Skills

Sales strategy development

Data-driven decision making

People management

Cross-functional collaboration

Tools

CRM systems

Salesforce

Job description

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 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.

Hear from

Al

“I love working at Thumbtack because I get to work with smart and motivated people who push me to do my best…It feels great to be part of a team that creates real impact every day.”

Al

Director Quality

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

Supporting you at work and beyond

• Paid time off
• Recharge with PTO, in addition to 20 company-wide holidays each year, including a week-long end-of-year shutdown.
• Remote work stipend and reimbursements
• $1,000 USD/$1,400 CAD annual stipend for professional development, self care, office set-up and more. We also provide cell phone and Wi‑Fi reimbursements.
• Support for parents and caregivers
• All parents receive up to 12 weeks of paid parental leave, and birthing parents receive 8 additional weeks, for a total of 20 weeks of 100% paid parental leave (US & CAN).
• Family formation benefits
• $30,000 USD/CAD lifetime max reimbursement for family planning.
• Mental health and financial coaching
• 12 coaching sessions and 12 therapy sessions for yourself and your dependents. We also offer one‑on‑one financial guidance from a financial wellness provider.
• Thumbtack Bucks
• $450 USD/CAD quarterly stipend to book a pro on Thumbtack for virtual or in-person services — anything from home care services to planning a child’s birthday party and beyond.

Claude Enterprise (Claude.ai, Claude Code, Cowork, Claude Desktop, Ask Thumbtack), OpenAI Enterprise ChatGPT & Codex, Cursor, Gemini Enterprise, Granola, Coda AI, Linear, and more.

*Access varies based on location, team, and role.