Product Support Specialist

About Rundoo Our mission is to empower independent supply stores with best-in-class technology. Think of your local hardware store or mom-and-pop nursery—these are our clients. From paint to lumber to flooring, over 200,000 such stores across the country sell over $1T of building materials annually using outdated, on-premises systems. We’re aiming to help them modernize so that they can continue to thrive. Backed by leading investors including Bessemer and CRV, we've raised $18M across three rounds and are growing quickly. Our team is made up of builders, sellers, and industry veterans with a shared goal: to bring modern technology to an overlooked industry. About The Role Location: Chicago (Hybrid) - 1 - 2x a week Working Hours & Coverage Coverage window: Our support line runs 5:00am CT – 8:00pm CT (a 15‑hour, coast‑to‑coast window), Monday‑Friday, with 8am - 6pm CT coverage on weekends. Your shift: You'll be based in Central time and work five 10‑hour days — roughly a 50‑hour week. This is a salaried, full‑time role. Your shift is typically the morning open (5:00am–3:00pm CT) or a mid shift (8:00am–6:00pm CT); comfort with an early start is required. We are hiring for 2 shifts: Opening Shift — Monday‑Friday, 5:00am–3:00pm CT Mid Shift + Weekends — Monday‑Wednesday, Saturday & Sunday, 8:00am–6:00pm CT (Thursday & Friday off) Cross‑training: Everyone on the team is cross‑trained across shifts and rotates fairly — no one is permanently assigned to weekends. The Role As a Product Support Specialist at Rundoo, you will be the primary point of contact for clients in their time of need. You'll help independent hardware and paint store owners solve problems across our full ERP platform—from POS transaction issues to inventory sync problems, accounting reconciliation, and user training questions. You'll work alongside Robbie and Tim to provide coast‑to‑coast coverage for our growing client base. This role is ideal for someone who thrives on problem‑solving, enjoys helping small business owners succeed, and wants to grow with a fast‑paced startup. You’ll report to Claire, Manager, Client Success, and collaborate closely with our Client Success and Engineering teams to ensure client needs are met and product improvements are identified. What You’ll Do Provide exceptional support via Intercom chat, email, and phone to hardware and paint store owners and their staff Resolve diverse technical issues including POS troubleshooting, inventory sync problems, accounting reconciliation, report generation, and user training questions Perform data analysis and reconciliation work using spreadsheets to investigate balance discrepancies and help clients understand their numbers Collaborate with Engineering to communicate customer issues, submit detailed bug reports with reproduction steps, and help troubleshoot technical problems Leverage AI‑assisted tools (Intercom AI, ChatGPT, Claude) to improve response quality, efficiency, and documentation Partner with Client Success team by escalating at‑risk accounts, identifying training needs, and flagging patterns that indicate broader issues Contribute to knowledge base by documenting solutions, creating help articles in Notion, and improving self‑service resources Maintain metrics including 80% customer satisfaction What We’re Looking For Essential Qualities We care more about aptitude and drive than checking boxes on years of experience. The ideal candidate is smart, hungry to learn, and thrives on solving problems independently. Core Competencies Exceptional attention to detail - You catch discrepancies others miss, especially when working with numbers and data Strong independent problem‑solver - You can troubleshoot ambiguous issues without constant hand‑holding Excellent written and verbal communication - You can explain complex concepts clearly to non‑technical small business owners Organizational excellence - You can manage multiple priorities, juggle competing tickets, and maintain composure during high‑volume periods Customer‑centric mindset - You genuinely enjoy helping people and build positive relationships even when customers are frustrated Comfort with ambiguity - You can navigate situations without clear answers and figure out solutions through research and creative thinking Valuable Experience (But Not Required) Prior customer support or technical support experience in any industry Experience with SaaS products or technology companies Accounting, bookkeeping, or financial reconciliation background Retail, POS, or small business operations experience Technical troubleshooting ability with software applications Technical Requirements Comfortable learning and becoming expert in complex software (our full ERP platform) Proficient with spreadsheets (Google Sheets/Excel) for data analysis Strong analytical skills for investigating balance discrepancies and data issues Able to work during required hours. Bonus Points Direct familiarity with or experience in paint and hardware, building materials, construction supply, or related industries Comfortable adapting to a dynamic startup environment where priorities shift and new challenges arise regularly Proven experience helping customers adopt new workflows or systems (change management) Experience with Intercom, Zendesk, or similar support platforms Compensation Base Salary: $83K Equity: $13,000 - $14,000 equity grant value Benefits: See below About The Team Claire (Manager, Client Success) Robbie (Product Support Specialist) Tim (Product Support Specialist) Reggie (Client Success Manager) Vidhan (Head of Client Experience) Interview Process Talent Screen: 20 minutes A conversational chat with Amanda, our founding recruiter, to get to know one another, share more about the role, and answer any initial questions you have. First Round: 30 minutes A conversation with Claire focused on your experience and background. Onsite Interview: River North, Chicago A half‑day on‑site where you’ll meet several members of the team: Escalation Role‑Play & Communication Skills (30 min) - with Leslie Troubleshooting Exercise (30 min) - with Robbie Team Conversation (15 min) - with Vidhan Lunch with the Team (1 hour) - an informal chance to connect with future teammates Final Call: 15 minutes Reference Check We’ll reach out to your provided references as a final step before extending an offer. About Our Founders Andrew (CTO): studied computer science & humanities at Stanford; worked as a software engineer and head of engineering at Apple & Anova; danced with the SF ballet (where he met his wife)! Nick (CEO): studied math & computer science at Stanford; worked as a trader at Bridgewater & Citadel and as a PM at Google & Enigma; distantly related to the founder of the Hershey company How we’ve fundraised A $2m pre‑seed led by Kent Bennett at Bessemer with participation from Plug & Play, Quiet Capital, and Sequoia. A $5m seed led by Caitlin Bolnick Rellas at CRV. An $11m series A led again by Bessemer and CRV. Compensation Range Compensation Range: $83K #J-18808-Ljbffr