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.

Job Summary

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.

Job Responsibilities

•      Prospect and generate new business opportunities through outbound outreach, networking, referrals, and attendance at local cybersecurity community events (ISSA, Cloud Security Alliance, etc.).

•      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 HubSpot - 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.

•      Out-of-state travel expected at approximately 3–4 days per month.

•      In your first 30 days, you will learn our product, our customers, and our sales process. By day 60, you will have met every current customer in person. By day 90, you will have a full pipeline of active opportunities and a clear plan for converting our free user base.

•      You will be selling 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.

•      Stern Security has hundreds of free users in the platform, representing a significant and immediate pipeline opportunity for the right candidate.

 

Job Skills & Qualifications

Required

1.    Proven track record of self-sourcing and closing deals - not just managing a handed pipeline or working warm inbound leads.

2.    Experience in a startup, SMB, or lean sales environment where you owned the full process independently. Candidates whose experience is exclusively at large enterprise organizations may not be the right fit for the pace and scope of this role.

3.    Demonstrated ability to do outbound prospecting from scratch - building lists, crafting outreach, and generating your own pipeline.

4.    Experience with free-to-paid conversion or product-led growth motions is a strong plus.

5.    Consultative selling skills - ability to listen, identify pain, and connect customer needs to solutions rather than leading with a pitch.

6.    Proficiency with CRM tools (HubSpot preferred) - disciplined about logging activity and maintaining an accurate pipeline.

7.    Sufficient technical fluency to demo our product confidently and discuss cybersecurity concepts with both technical and non-technical buyers.

8.    Reliable and consistent availability for in-person customer meetings and occasional evening professional events. A predictable schedule is essential to building trust with customers and prospects.

9.    Highly self-motivated, accountable, and organized - able to manage your own time and priorities without day-to-day direction.

Preferred

1.    Cybersecurity industry experience or familiarity with compliance frameworks (SOC 2, CIS, NIST, etc.).

2.    Experience selling SaaS and/or professional services (pen testing, vCISO, managed security, etc.).

3.    Prior experience in a founder-led or early-stage company.

4.    Positive, calm demeanor with a proactive, ownership-driven approach.

 

Benefits

• 100% Company paid medical/dental/vision for employees.
• 4% match on company retirement plan
• 3 weeks mandatory vacation per year + all federal holidays

 

Additional Compensation

• Variable Commission
• Equity