Account Executive

Stern Security Inc. Account Executive, Raleigh, NC - Full Time

The Account Executive is responsible for driving pipeline growth and closing new business at Stern Security. This is a hunter role at its core – the right candidate thrives on outbound prospecting, building relationships from scratch, and converting opportunities without relying on inbound leads or a large support team. You will own outreach to new prospects, work existing customers for upsell and expansion, and engage our free user base to convert them to paid accounts.

A key near‑term priority is building relationships ahead of a new product offering launching in Q3 2026, which represents a significant upsell opportunity within our current user base. This position reports to the CEO.

Stern Security is an innovative cybersecurity company headquartered in Raleigh, NC. Our premier product is Velocity, the most effective and accurate cybersecurity insights platform based on internal and third‑party risk assessments. Our services include some of the best Penetration Testing your company will ever see and insightful vCISO work.

• Prospect and generate new business opportunities through outbound outreach, networking, referrals, and attendance at local cybersecurity community events.
• Identify, engage, and convert free users in the Stern Security platform into paid customers using usage data and engagement signals to prioritize outreach.
• Grow existing customer accounts through upsell and expansion, including positioning the new Q3 2026 product offering to current customers and free users.
• Own the full sales cycle for your opportunities: outreach, discovery, product demos, follow‑ups, proposals, and closing.
• Maintain a cadence of at least three in‑person customer and prospect touchpoints per week, including coffee meetings with existing customers, visits with new prospects, and event attendance.
• Maintain a clean, accurate pipeline in Hub Spot – logging activity, updating deal stages, and forecasting consistently.
• Collaborate with the CEO on deal strategy and closing support for larger or more complex opportunities.
• Work cross‑functionally with the product and delivery teams to ensure smooth handoffs and customer satisfaction.
• Provide feedback from prospects and customers to inform product development and messaging.
• Support the delivery team by occasionally visiting customer sites to assist with lightweight technical tasks – turning operational touchpoints into relationship‑building and account growth opportunities.
• Travel out of state approximately 3–4 days per month.
• In your first 30 days, learn our product, customers, and sales process; by day 60, meet every current customer in person; by day 90, have a full pipeline of active opportunities and a clear plan for converting our free user base.
• Sell to security and risk leaders, including CISOs, VPs of Information Security, Heads of Risk, CIOs, and operational buyers such as Heads of Vendor Management and Supply Chain.
• Leverage the hundreds of free users in the platform as a significant and immediate pipeline opportunity.

• Cybersecurity industry experience or familiarity with compliance frameworks (SOC 2, CIS, NIST, etc.).
• Experience selling SaaS and/or professional services (pen testing, vCISO, managed security, etc.).
• Prior experience in a founder‑led or early‑stage company.
• Positive, calm demeanor with a proactive, ownership‑driven approach.

• Company‑paid medical/dental/vision for employees.
• 4% match on company retirement plan.
• 3 weeks mandatory vacation per year plus all federal holidays.