Job Details

This is a high-volume position that we fill often. By applying, you'll be added to our priority list for upcoming openings. Thank you for your interest in joining Leap - let's stay in touch!

Hiring Locations: Must be based in either the Chicago, IL or Baltimore, MD markets

About Us

At Leap, we're on a mission to transform the home improvement industry - and we want you to be part of that journey. We're proud to be recognized on the Inc. 5000 and Inc. Regionals lists for 5+ consecutive years, reflecting sustained growth driven by innovation, strong execution, and an incredible team. We build technology that helps contractors work smarter, scale faster, and deliver better experiences to their customers.

When you join Leap, you'll work alongside curious minds, bold innovators, and thoughtful risk-takers who care deeply about doing great work - and doing it together. Our culture is transparent, supportive, and grounded in approachable leadership. We actively listen to our employees through semi-annual engagement surveys, maintain a strong eNPS score, and consistently act on feedback to improve what's working and where we can do better. We believe great work happens when people are supported outside of work, which is why we offer comprehensive benefits and wellness resources for you and your family.

Take the Leap today and help shape what's next.

Position Overview

The Product Specialist is responsible for managing escalated and email-based support cases across Leap's product suite. This role partners closely with the frontline Support team to resolve more complex customer issues and ensure timely, accurate case resolution.

The Product Specialist serves as a key bridge between Support and Product, helping to document issues clearly and contribute to overall product and process improvements.

Responsibilities

• Manage escalated and email-based support cases across Leap's products
• Conduct in-depth troubleshooting for complex customer issues that require additional investigation beyond frontline support
• Partner with frontline agents to gather necessary context and ensure smooth handoffs
• Document case details thoroughly within the case management system
• Submit Jira tickets with clear reproduction steps and relevant details when issues require Product or Engineering review
• Follow up on escalations to ensure timely resolution and communication back to customers
• Maintain internal documentation and contribute to knowledge base updates
• Identify recurring issues and share trends with leadership
• Support onboarding and training of frontline agents on more advanced workflows

Qualifications

• 2-4 years of experience in technical support or client-facing SaaS support
• Strong troubleshooting and problem-solving skills
• Experience supporting web-based applications
• Ability to clearly communicate technical concepts in a customer-friendly way
• Strong organizational skills and ability to manage multiple cases
• Experience using case management or ticketing systems (e.g., Jira, Zendesk, Salesforce, etc.)
• Detail-oriented with a high level of ownership
• Associate/Bachelor's degree or equivalent experience required
• Spanish fluency a plus

Benefits

We believe in supporting our employees holistically - your health, financial well-being, time to recharge, and overall happiness matter to us. Here's what you can look forward to:

• Affordable Health & Wellness Coverage- comprehensive and competitive benefits package, starting the first of the month following your hire date.
• Invest in Your Future- 401(k) company match to help you build financial security.

• Time to Recharge- We believe time to rest and recharge matters. Leap offers a Flexible Time Off (FTO) policy, 10 paid sick days, and 8 paid company holidays.
• Comprehensive Employee Assistance Program (EAP)- resources to support your mental health, financial well-being, and everyday challenges.
• Exclusive Discounts withLifeMart(via ADP)- save on groceries, restaurants, entertainment, pet insurance, cell phones, child care, and more!
• MoveSpringWellness App- stay active and engaged with company step challenges, workout content, meditation tools, and wellness blogs for a healthier you!
• Culture & Team-Building Activities- we love to connect, celebrate, and grow together through team events, fun challenges, and company traditions like our Annual Summit!

Join us and experience a company that truly invests in YOU!

Leap is an Equal Employment Opportunity and Affirmative Action Employer. We are committed to providing an environment of mutual respect where equal employment opportunities are available to all applicants and teammates without regard to race, religion, color, sex, gender identity, sexual orientation, age, non-disqualifying physical or mental disability, national origin, veteran status or any other basis covered by appropriate law. All employment decisions are made based on qualifications, merit, and business needs.