Founding Sales Development Representative (SDR)

Location: Chicago, IL Headquarters

Type: Full-time, in office

Company Stage: Early-stage / startup

We're a small, fast-moving team building something new. The right person for this position is ambitious, organized and comfortable starting conversations with people they've never met. You'll be our first dedicated SDR, which means you won't just run a playbook, you'll help write it. Early-stage startup life means shifting priorities, lean resources and high expectations, and that should energize you rather than slow you down. If you want real ownership, a direct line to how the company grows, and a path to build a career in sales, keep reading.

At Autopilot, our mission is to free people up to do what they do best by automating everything else. We are building the infrastructure layer that powers autonomy in motion across the physical world, including sports, fitness, logistics, healthcare and more. Our systems help robots move, record, deliver, train and connect in real-world environments that have historically lacked modern tooling. Our values are simple and non-negotiable: Do Good. Have Fun. Make Money. We believe these are mutually reinforcing, and we work hard to uphold them as we grow.

We move fast, operate scrappy, and care deeply about building something that works.

You will be eligible to participate in company benefits and perks, which currently include:

• Base Salary Uncapped Commission
• The base salary range for this role is $65,000-$75,000, depending on experience. On-target earnings are ~$100,000. Variable compensation is uncapped, paid monthly, and tied to completed, qualified meetings and sales-accepted opportunities.
• 100% Employer-covered Health, Dental, and Vision Insurance
• 401(k) - Company-administered plan
• Flexible PTO - Time off as needed, coordinated with your team
• 18 Paid Holidays
• Travel Reimbursement - Reimbursed in accordance with company policy, where role-related travel is required
• Team & Culture Events - Team offsites, social events, and company-sponsored activities

Benefits and policies may be updated from time to time at the company's discretion.

We're looking for a Founding SDR who turns interest in robotics into real customer conversations. You'll build a qualified pipeline through outbound prospecting and fast follow-up on inbound leads: researching accounts, reaching the owners, operators and facility leaders who make buying decisions, qualifying fit, and booking discovery meetings with our account executives. Because you're the first person in this seat, you'll also help shape how we prospect. What you hear from prospects (objections, questions, what lands and what doesn't) goes straight back into our messaging, sequences and playbooks. You'll work in person with our sales and marketing teams in Chicago and see exactly how your work moves the company forward.

Outbound Prospecting

• Identify target accounts and the owners, operators and facility leaders responsible for purchasing decisions
• Start conversations through phone calls, personalized emails and LinkedIn outreach
• Explain Autopilot's value in practical terms: less manual work, more consistent operations, and robots that actually get used
• Run outreach sequences, follow up persistently, and test ways to improve response rates

Inbound Lead Qualification

• Respond quickly to leads from marketing campaigns, events, referrals and our website
• Understand the prospect's facility, current processes, challenges and purchasing timeline
• Assess fit against our qualification criteria and identify the right next step
• Schedule discovery meetings and provide clear notes so account executives can pick up where you left off

Meeting Attendance & Pipeline Management

• Confirm meetings and follow up with prospects to improve attendance
• Re-engage prospects who miss meetings or need more time
• Keep HubSpot current with accurate contact information, activity records, qualification notes and next steps
• Coordinate with account executives on handoffs and follow-up priorities

Build the Sales Development Motion

• Help write and refine our first SDR playbooks, outreach sequences and messaging
• Work with account executives to sharpen our qualification criteria based on what actually converts
• Share common objections, customer questions and prospect feedback with sales and marketing
• Use AI tools for account research and personalized outreach while keeping accuracy and quality high

• A consistent flow of completed, qualified discovery meetings
• Opportunities that meet our qualification standards and are accepted into the sales pipeline
• Fast lead response and reliable follow-through
• Accurate CRM records and useful handoffs
• Steady improvement in outreach effectiveness and conversion

You start conversations and follow through

• You're comfortable picking up the phone and talking to people you haven't met
• You listen carefully, ask thoughtful questions and communicate clearly
• You're organized and dependable. You keep track of commitments and follow through on every one

You're coachable and driven

• You can handle rejection, take coaching and apply feedback quickly
• You're motivated by goals and curious about how businesses make buying decisions
• You enjoy working in person with a small team where priorities evolve and individual contributions matter

Experience

• 2-4 years in sales development, inside sales or a customer-facing role with real prospecting or cold-calling experience
• Able to prospect independently, qualify effectively and help improve messaging and playbooks
• Technology sales experience is a plus, SaaS preferred. Bonus points if you've sold robotics or automation
• Familiarity with HubSpot or another CRM
• Experience selling into, or working in, a vertical we serve, including but not limited to healthcare, commercial real estate, logistics, warehousing or manufacturing
• AI-comfortable in your day-to-day: you use tools like Claude, ChatGPT or similar to research faster and write better
• Interest in robotics, automation or technology
• Ability to work onsite at our Chicago headquarters
  

Submit your resume and LinkedIn profile, along with a brief note about why you're interested in sales and Autopilot.

Autopilot is an equal opportunity employer. We welcome applicants of all backgrounds. If you need an accommodation to apply, contact takeoff@operationautopilot.com.