Product Support Specialist at Rundoo (Chicago, IL)Product Support Specialist

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to lumber to flooring, over 200,000 such stores across the country sell over $1T of building materials annually using outdated, on-premises systems.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 Battery, Bessemer and CRV, we've raised $48M across four rounds and are growing quickly: We're live in over 500 stores across the USA, Canada, and the Caribbean, and integrated with over 20 industry partners. Our team is made up of builders, sellers, and industry veterans with a shared goal: to bring modern technology to an overlooked industry.

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.

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.

• Provide exceptional support via Intercom chat, email, and phone to hardware and paint store owners and their staff
• Diagnose issues through structured discovery (e.g. is it a product bug, a training gap, or a workflow mismatch?), before proposing a fix
• 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 <24hr resolution time for 90%+ of tickets, <5min average first response time, and >80% customer satisfaction

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
• Empathy for small business owners under pressure - paired with the composure to de-escalate a frustrated conversation
• Skilled at asking questions - ones that get past the stated symptom to the actual root cause

Valuable Experience (But Not Required) Any of the following backgrounds could set you up for success:

• 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

• Base Salary: $83K
• Equity: $13,000 - $14,000 equity grant value
• Benefits: See below

Here is the current makeup of the teams you’ll be working most closely with:

• Claire (Manager, Client Success)
• Robbie (Product Support Specialist)
• Tim (Product Support Specialist)
• Reggie (Client Success Manager)
• Vidhan (Head of Client Experience)

Interview Process 🎤

1. 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.
2. First Round: 30 minutes A conversation with Claire focused on your experience and background.
3. 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 (30 min) - with Tim
• Lunch with the Team (1 hour) - an informal chance to connect with future teammates

1. Final Call: 15 minutes A quick conversation with Nick to wrap up and address any remaining questions.
2. Reference Check We'll reach out to your provided references as a final step before extending an offer.

• Andrew (CTO): studied computer science & humanities at Stanford, worked as a software engineer at Apple and head of engineering at 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 🍫

We've raised $48m across four rounds:

• 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.
• A $30m series B led by Battery.