--- title: 'Account Executive at Rundoo' canonical: 'https://feeny.ai/job/account-executive-rundoo-chicago-fsy32ahknky2' type: 'job' last_seen: '2026-09-13' --- # Account Executive at Rundoo - **Company:** Rundoo - **Location:** Chicago, IL - **Compensation:** $55k–$92k - **Employment:** full-time - **Work type:** onsite - **Posted:** 2026-05-07 - **Last confirmed live:** 2026-09-13 - **Apply:** https://jobs.ashbyhq.com/rundoo/584e89ba-753e-4552-b893-827b74c37207 ## Job description ## 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to lumber to flooring, over 200,000 such stores across the country sell over $1T of building materials annually using outdated, on-premises systems.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 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. What you’ll do as an Account Executive at Rundoo 🗒️ 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. 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. ## 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. Bonus points 🌟 - 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 (30 min) - Remote: - An informal conversation with our Recruiting Team to get to know one another. - Round 1 (30 min) - 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 (15 mins) - Remote: Call with our CEO, Nick. - Reference Check - Offer ## About 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. ## Compensation 💵 - Salary: $92,000 annually - Commission: $100,000 annually (based on performance and targets met) - OTE Potential: $192,000 annually, with no cap - Equity: $54,794 initial grant value, vesting over 4 years ## Benefits 🏋️ - Full medical, dental, and vision coverage (100% of premiums for you, 50% for dependents) - Life Insurance - 401k with Betterment - Unlimited PTO with 10 company paid holidays - In-office gym - Daily team lunches - Learning materials and audiobook subscriptions - We use Carta Total Rewards to benchmark a competitive compensation package: - Base Salary: $92K - Uncapped Commission (On-Target Earnings): $192K - In addition to base and commission, you’ll receive an equity package. ## About our founders 🌲 - [Andrew](https://www.linkedin.com/in/beckman-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](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 $48m across four 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. - A $30m series B led by [Battery.](https://www.battery.com) ## About Rundoo ## Company Overview - **One-liner**: Rundoo provides an AI-first, cloud-based point-of-sale and operations platform purpose-built for independent hardware, paint, farm & feed, lumber, and lawn & garden supply stores. - **Entity Type**: Private (Series A, total funding $18M) - **Headquarters**: Redwood City, California, USA (additional office in Chicago) - **Founded**: 2021 - **Founders**: Andrew Beckman (CEO & Co‑founder) and Nick Hershey (CTO & Co‑founder) ## Core Business - **Primary industry/industries**: Retail technology / point-of-sale (POS) software for independent building and agricultural supply stores. - **Target customers**: Independent hardware stores, paint stores, farm & feed stores, lumber yards, lawn & garden centers (SMB / independent, B2B). - **Mission or purpose**: Modernize the 200,000+ independent supply stores in the U.S. by replacing outdated, cobbled-together software with an AI-powered platform that makes it easier to run the business and serve customers better. ## Products & Services - **Rundoo POS & Operations Platform**: A complete, web-based point-of-sale system with integrated payment processing, inventory management, customer accounts, and reporting. Designed to handle specialty workflows like paint tinting, seasonal demand, contractor pricing, and co-op catalogs. - **Rundoo AI**: A set of AI features that use the store’s own sales, inventory, and charge‑account data to generate purchase orders, run price comparisons against nearby competitors, and answer natural‑language questions (e.g., “Which products lost margin last month?”). - **AI Order Generation**: Automatically writes purchase orders based on historical sales, low stock, and seasonal trends. - **AI Price Comparisons**: Shows how the store’s prices stack up against local competitors and suggests adjustments. - **AI‑Generated Reports**: Responds to plain‑English questions with instant reports and insights. ## Market Standing - **Valuation**: Not disclosed (private company) - **Key Metric**: Total funding of **$18M** (Series A closed ~2024, $11M last round) - **Notable Investors/Partners**: Bessemer Venture Partners, CRV, Sequoia Capital, Plug and Play Ventures, Quiet Capital (and 6+ others) - **Growth Signals**: - **500+** independent stores across the U.S. and Canada on the platform. - Stores using Rundoo see an average **17% increase in top‑line sales** and a **2‑point increase in gross margin** in the year after go‑live. - Charge‑account balances drop by **25%** (faster collections). - Strong hiring momentum: 50 total employees (20 product + tech) with open roles across R&D, GTM, and G&A. ## Competitive Advantages - **AI‑first, purpose‑built platform**: Unlike general‑purpose POS systems, Rundoo is built specifically for independent supply stores, handling specialized workflows (tinting, bulk, standing orders, contractor pricing, seasonal demand). - **Proven ROI**: Measurable, documented improvements in revenue (+17%), margin (+2 points), and receivables (-25%) for early adopters. - **Data moat**: The AI models are trained on each store’s own data, making them more accurate and actionable than generic tools. - **Integrated ecosystem**: Partners with major brands and buying groups, reducing friction for stores that switch. ## Strategic Focus - **Deepen AI capabilities**: Make the platform “like your best employee” with increasingly autonomous ordering, pricing, and reporting. - **Expand into new verticals**: The platform already serves hardware, paint, farm & feed, lumber, and lawn & garden; a “Product Manager, New Industries” role signals intent to enter adjacent segments. - **Scale the customer base**: Grow from 500 to thousands of stores in the U.S. and Canada, leveraging AI as a key differentiator against legacy incumbents. - **Build the team**: Aggressively hiring across engineering, data science, product, sales, and implementation to fuel growth. ## Why Work Here - **Impact**: Work on a product that directly helps small‑business owners survive and thrive against big‑box competitors—measurable results. - **Culture**: Hybrid model (4 days in office, Thursday WFH) with offices in Redwood City (R&D) and Chicago (GTM). Open, AI‑first engineering culture. - **Benefits**: - 100% of medical, dental, and vision premiums for employees; 50% for dependents. - Company‑paid life & AD&D insurance (1x salary). - 401(k) with Betterment. - Unlimited PTO + 10 company‑paid holidays. - Daily team lunches. - Monthly gym membership. - Learning materials and audiobook subscriptions. - **Growth stage**: Early‑stage private company with strong venture backing and proven traction—opportunity to shape products and processes as the company scales. - **Remote options**: Some roles (e.g., Account Executive, Sales Development Representative) are remote; engineering positions are headquartered in Redwood City. ## Sources 1. [rundoo.ai](https://rundoo.ai/) – Product overview, AI features, customer results, partner logos. 2. [rundoo.ai/careers](https://rundoo.ai/careers/) – Mission, founders, benefits, open roles. 3. [builtin.com](https://builtin.com/company/rundoo) – Headcount (50 total, 20 product+tech), offices, hybrid schedule, perks. 4. [cbinsights.com](https://www.cbinsights.com/company/rundoo) – Founding year (2021), total funding ($18M), Series A, investor list. 5. [jobs.ashbyhq.com](https://jobs.ashbyhq.com/rundoo) – Current job postings (implementation, sales, engineering, data science, recruiting). ## Other roles at Rundoo - [Operations Lead - Billing, Reconciliations, & Buyouts](https://feeny.ai/job/operations-lead-billing-reconciliations-buyouts-rundoo-metro-manila-ttqk39bygzja) — Metro Manila - [Growth Marketing Manager](https://feeny.ai/job/growth-marketing-manager-rundoo-redwood-city-pc3gw8gef3ma) — Redwood City, CA - [Product Manager, New Industries](https://feeny.ai/job/product-manager-new-industries-rundoo-redwood-city-yc0kdxxzqfpw) — Redwood City, CA - [Product Support Specialist](https://feeny.ai/job/product-support-specialist-rundoo-chicago-jgvv1qcq1ymz) — Chicago, IL - [Partner Growth Manager](https://feeny.ai/job/partner-growth-manager-rundoo-redwood-city-9vf203q3j3qx) — Redwood City, CA - [Tech Recruiter](https://feeny.ai/job/tech-recruiter-rundoo-redwood-city-887scasbfecy) — Redwood City, CA - [Sales Development Representative](https://feeny.ai/job/sales-development-representative-rundoo-chicago-6vg4nb6kpk1w) — Chicago, IL - [Software Engineer](https://feeny.ai/job/software-engineer-rundoo-redwood-city-54d362vwcfgx) — Redwood City, CA - [Implementation Manager](https://feeny.ai/job/implementation-manager-rundoo-chicago-0b5pn1zfgk57) — Chicago, IL - [Account Executive](https://feeny.ai/job/account-executive-kernel-san-francisco-7h92f9x7djp1) — San Francisco, CA