Account Executive, Chicago (Software Startup)

About the role

This is a closing role. You’ll be expected to run sharp discovery, quantify value, navigate stakeholders, handle objections, and negotiate commercially, while partnering closely with SDRs/BDRs, Growth, Marketing, and Product to improve conversion and expand what we can sell.

Responsibilities

• Own the full sales cycle
• - Run discovery calls with founders and operators at scaling food and consumer goods companies
• - Diagnose operational pain, cashflow pressure, margin constraints, and supply chain risk
• - Build clear business cases and ROI logic (time saved, waste reduced, margin impact, cashflow benefit)
• - Lead product demos and map Opply’s value to customer workflows and priorities
• - Manage the deal cycle through proposal, negotiation, and close
• Close revenue, consistently
• - Forecast accurately and maintain clean, reliable pipeline in the CRM
• - Handle objections confidently (pricing, switching risk, incumbent suppliers, internal bandwidth)
• - Negotiate commercial terms and drive urgency through clear next steps
• - Partner with internal teams to remove blockers and increase win rates
• Expand and improve the motion
• - Share market feedback to sharpen positioning, outreach, and product priorities
• - Identify patterns in lost deals and propose improvements to process, messaging, or packaging
• - Represent Opply at industry events - building relationships, credibility, and deal flow
• Market intelligence
• - Keep the CRM clean, accurate, and actionable (your pipeline is your reputation)
• - Share insights from the market with Growth, Marketing, and Product to sharpen targeting and messaging
• - Represent Opply professionally at industry events and in the broader market

Requirements

• You'll thrive here if you are:
• - A closer: You’re at your best when you’re running live deals and driving to signature
• - Consultative and structured: You ask smart questions, listen properly, and build strong cases for change
• - Commercially sharp: You can speak credibly about value, outcomes, and trade-offs
• - Resilient and consistent: You don’t rely on “big wins”you build repeatable performance
• - High ownership: You take initiative, solve problems, and keep momentum even with ambiguity
• - Analytical - you can draw insights and report to wider business with ease.
• Experience we expect:
• - 2- 5 years in sales or business development (B2B strongly preferred)
• - 1 year minimum in a closing role (B2B strongly preferred)
• - Track record of hitting or exceeding targets (consistent performance, not one-off wins)
• - Interest or experience in food/consumer goods is a plus, but hunger and aptitude matter more
• - Experience in selling software / technology to SMB markets

Qualifications

• Experience in selling software / technology to SMB markets

Skills

• Modern discovery: Combine qualitative insight with quantitative value logic to uncover real urgency
• Commercial fluency: Speak credibly about cashflow, operational efficiency, and growth readiness
• Market expertise: Deep understanding of the scaling F&B world (supply chain challenges, margin pressure, and what operators actually care about)
• Unshakeable confidence: Built through repetition, feedback, and high standards

Benefits

• Compensation base salary ($70,000–$80,000) + uncapped OTE (Year 1 OTE $40,000)
• Flexible hybrid working (balance autonomy with collaboration)
• Regular team socials and global offsites to connect, collaborate, and celebrate
• Health Insurance
• Pension scheme

Schedule

3-5 days per week + travel to events within territory

Locations

Chicago

Remote status

Hybrid