ABOUT RUNDOO ℹ️
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to lumber to flooring, over 200,000 such stores across the country sell over $1T of building materials annually using outdated, on-premises systems.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.
WHAT YOU'LL ACHIEVE WITH US 🥇
You'll be on the ground floor of a high-growth, venture-backed startup reshaping how building materials retailers run their businesses.
- You'll be based out of Chicago / Chicagoland and lead the entire sales process from lead generation to close. This role is primarily outbound sales through a combination of inside and outside sales strategies. You’ll report to Rundoo’s Head of Sales, and work closely with a team of peers who do the same role in other regions: Kyle https://linkedin.com/in/kyle-flechsig/, Ryan https://www.linkedin.com/in/ryanaugustine/, Sam https://www.linkedin.com/in/samfew/, and Andy https://www.linkedin.com/in/andymikeska/. Plus, you will collaborate closely with industry veterans like Reggie https://www.linkedin.com/in/reggie-bowles-9989082a/ and a team of accomplished implementation professionals and BDRs.
- You’ll spend about 50% of your time in-person in office, collaborating closely with team members, and 50% traveling throughout your territory to meet customers in-person.
- We use Carta Total Rewards to benchmark a competitive compensation package:
- Uncapped Commission (On-Target Earnings): $192K
- In addition to base and commission, you’ll receive an equity package.
REQUIREMENTS ✅
- You live in the Chicago / Chicagoland area and can work from our office ~50% of the time.
- You are excited to close deals and carry a quota.
- You have a valid U.S. driver’s license.
- You’re energized by frequent travel (~50%) across your assigned states.
- You love building strong relationships with customers: from first conversation through close.
ICING ON THE CAKE 🎂
- You've successfully closed new business deals in the $15K–$20K ARR range, especially at Series A startups or companies in a similar growth stage.
- You have experience hunting and closing net-new business in a field sales role.
- You’re familiar with the building materials or construction supply industry: ideally retail.
- You love friendly competition and thrive in a high-performance team.
- You’ve sold a product that is new to the market or required process change for the customer.
INTERVIEW PROCESS
- Intro Call (20 min) - Remote: An informal conversation with our Recruiting Team to get to know one another.
- Round 1 (1 hour total) - Remote: A fast-paced learning session with Matt, our Head of Sales:
- Cold Call Exercise: How you qualify prospects, uncover pain points, and set up the next steps in the conversation.
- Experience Discussion: Diving into your sales background and talk about the skills and qualities that will help you succeed in this role.
- Round 2 (2 hours total) - In-person:
- Discovery: Understanding the prospect’s pain points and how Rundoo solves them.
- Demo: Showcasing how Rundoo meets the prospect's needs.
- Close: Closing the deal or disqualifying based on the conversation.
- Lunch: If your interview falls near lunch or dinner, you'll join Matt for a meal. If you can't make it, we'll find another time.
- Founder Chat - Remote: Call with our CEO, Nick.
MEET THE TEAM
Sales
- Andy https://www.linkedin.com/in/andymikeska/ - An Oklahoma State alum (Go Pokes!) and proud dad with over 10 years of tech sales experience, this team member has found a passion at Rundoo in helping the Davids of the world take on Goliath—giving small businesses the tools and technology they need to win big. When not working with customers, there’s a good chance you’ll find them on the golf course, fully embracing the role of weekend warrior.
- Luke https://www.linkedin.com/in/lukerastetter/ - Once a high school Religious Studies and Psychology teacher, later inspired by the Steve Jobs era at Apple Retail to dive into tech. That spark led to a career in SaaS with Salesforce and G2, blending teaching roots with a passion for helping people solve problems through software.
- Matt - https://www.linkedin.com/in/matthew-kestufskie/Studied history at Northwestern; taught middle school in Chicago, led sales for a consumer goods start-up, joined Rundoo as an AE and now leads the sales team; former competitive angler (bass fishing 🎣) and current husband and father (👶)
- Reggie http://www.linkedin.com/in/reggie-bowles-9989082a - With 39 years in the paint and decorating industry, including time as a Benjamin Moore rep, 20 years as a store owner, and 13 years selling retail management systems, this team member has seen it all. Excited by Rundoo’s rapid growth and the move into hardware and supply stores, they’re passionate about bringing the latest POS technology to independent retailers.
- Ryan https://www.linkedin.com/in/ryanaugustine/ - A husband, dad, and sales lead at Rundoo, always passionate about family, the outdoors, and lowering the golf handicap. Success means working hard, having fun, and making a positive impact along the way.
- Sam http://www.linkedin.com/in/samfew - Helping small businesses do more than just run efficiently—helping them thrive. As Franklin County Paint put it: “This go-live was the most excited I’ve been about my business in over 15 years.” Built on a family atmosphere, the focus is always on lifting others up and celebrating wins together.
ABOUT OUR FOUNDERS 🌲
- Andrew https://www.linkedin.com/in/beckman-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 https://www.linkedin.com/in/hershey-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 💰
We've raised $18m across three rounds:
- A $2m pre-seed led by Kent Bennett https://www.bvp.com/team/kent-bennett at Bessemer https://www.bvp.com/ with participation from Plug & Play, Quiet Capital, and Sequoia.
- A $5m seed led by Caitlin Bolnick Rellas https://www.crv.com/team/caitlin-bolnick-rellas at CRV https://www.crv.com/.
- An $11m series A led again by Bessemer and CRV.