Pro Success Manager

Employee Resource Groups

8+ ERGs across North America and the Philippines, including Parents ERG and groups focused on racial/ethnic, gender, and LGBTQ+ identities.

Employee Recognition Awards

Formal employee awards program recognizing contributions across the organization.

Team Events & Social Budget

Company-sponsored social events including happy hours, outings, local community meetups in 30+ cities, and virtual concerts and celebrations.

Volunteer Time Off

Opportunities to volunteer in the local community and partnerships with nonprofits.

Employee Product Discount

$450 USD/CAD quarterly Thumbtack Bucks stipend ($1,800/year) to book a professional on the Thumbtack platform.

Parental Leave (Birthing Parent)

20 weeks paid leave for birthing parents in the US and Canada; 105 days for birthing parents in the Philippines.

Parental Leave (Non-Birthing Parent)

12 weeks paid parental leave for all non-birthing parents, including adoptive and foster parents.

Fertility & Family Formation Benefits

$10,000 per year with a $30,000 USD/CAD lifetime maximum for covered infertility treatments, gender dysphoria services, and adoption assistance.

Adoption Assistance

$10,000 per year ($30,000 lifetime max) for adoption-related expenses, bundled with the family formation HRA.

Childcare Benefits

Childcare benefits for employees with families.

401(k) / Retirement Plan

401(k) and Roth 401(k) retirement savings plans available to employees.

Equity / RSUs

RSU equity grants with a 4-year vesting schedule (25% Year 1, then 3.13% quarterly Years 2-4).

Pay Transparency

Salary ranges published in all job postings with geo-tiered compensation across at least 3 tiers.

Financial Planning & Wealth Management

One-on-one financial wellness coaching plus access to Northstar and Wealthfront wealth management services.

Learning & Development Budget

Continuing education stipend, tuition reimbursement, online course subscriptions, job training and conference attendance, and personal development training.

Mentorship Program

Formal mentorship program and virtual coaching services including BetterUp professional coaching.

Defined Career Pathways

Customized development tracks with internal promotion pathways and structured career progression.

Health Insurance

Full medical insurance coverage. In the Philippines, includes HMO for self plus up to 3 dependents including common-law and same-sex domestic partners.

Dental Insurance

PPO dental plan covering employees and dependents.

Vision Insurance

Vision insurance coverage for eye exams, glasses, and contacts.

Life & AD&D Insurance

Life insurance and AD&D coverage at 2x annual salary, up to a maximum of $600,000.

Disability Insurance

Short-term disability at 60% of salary up to $3,000/week (180-day max) and long-term disability at 60% of salary up to $15,000/month (to age 65).

Health Savings Account (HSA)

HSA with $1,400/year employer contribution for individuals and $2,800/year for families.

Flexible Spending Account (FSA)

Pre-tax flexible spending account for healthcare and dependent care expenses.

Mental Health Benefits

12 coaching sessions and 12 therapy sessions per year via Modern Health for employees and dependents, plus access to multicultural and diverse therapists through Therify.

Pet Insurance

Company-subsidized pet insurance coverage.

Gender Affirming Care

Coverage for gender dysphoria services through the family formation HRA, plus transgender healthcare benefits and abortion travel benefits.

Employee Assistance Program

EAP through Modern Health providing mental health and well-being support for employees and dependents.

Home Office / Remote Work Stipend

$1,000 USD annual remote work stipend ($1,400 CAD; PHP 46,600) paid semi-annually for professional development, self-care, and office setup.

Cell Phone & Wi-Fi Reimbursement

Cell phone and Wi-Fi reimbursements for remote employees in North America.

Company Offsites / Retreats

Regular in-person offsites and team events (1-2x/year for ICs, 2-3x for managers, 4-6x for leaders), plus Camp Thumbtack and access to SF collaborative workspace.

International Work Allowance

Up to 60 days per country per calendar year of international work, limited to no more than 15 consecutive calendar days outside the Americas.

Unlimited / Flexible PTO

Flexible PTO policy allowing employees to take time off as needed.

Paid Holidays

18-20 company-wide paid holidays per year, significantly exceeding the US average.

Company Shutdown Days

Company-wide shutdowns in both summer and winter, including a week-long end-of-year shutdown in December.

Flexible Schedule

Core synchronous collaboration hours from 9 AM - 3 PM PT with No Meeting Wednesdays. Outside core hours, employees manage their own schedule.

Bereavement Leave

Paid bereavement leave following the death of a family member or loved one.

Extended Medical Leave

100% of pay for up to 8 weeks for medical leave, with additional weeks covered through short-term disability.

Paid Sick Days

Paid sick days for employees.

Fitness & Lifestyle Stipend

Up to $1,200 per year via Twic Lifestyle Spending Account for fitness, wellness, and lifestyle expenses, plus a separate fitness stipend.

Wellness Programs

Comprehensive wellness programs including weekly Wellness Wednesday yoga sessions featuring a Thumbtack pro, wellness days, and wellness-focused subscriptions.