Job Title: Account Executive
Location: Mississauga (Hybrid – 3 days/week in office)
Job Type: Full-Time
About DataStealth:
DataStealth is a single, unified data security platform (DSP) that discovers, classifies, and protects sensitive data across your entire environment, from on-premise to legacy cloud to cloud; wherever your data lives or flows, we protect it. We do this without requiring complex integrations or changes to your existing applications, ensuring security that enables, rather than hinders, your business. By seamlessly applying data protection strategies, such as tokenization, we ensure that even if your perimeter is breached, your data remains unusable if it falls into the wrong hands.
Recognized for the fifth consecutive year as a Great Place to Work, we are one of the world’s leading and fastest growing cybersecurity software companies. Our team is the best in the business. Our patented technology provides our large enterprise customers with the ability to solve complex data security problems with a paradigm shifting technology that can actually solve problems.
About You:
We are seeking a senior Account Executive with deep cybersecurity expertise to drive customer acquisition and revenue growth. This is not a “pitch deck” sales role. The ideal candidate is a borderline Subject Matter Expert (SME) in cybersecurity who can confidently engage CISOs, architects, and compliance officers, while also navigating complex procurement and business decision cycles.
Position Overview:
The Account Executive (AE) at DataStealth is responsible for owning the full sales cycle: from prospecting to closing enterprise deals. Success in this role requires three dimensions of excellence:
- Sales Acumen – Proven ability to run complex enterprise sales processes, with multiple stakeholders and long sales cycles.
- Technical Depth – Credibility to discuss encryption, tokenization, cloud security, compliance frameworks, and integrations at a near-SME level.
- Trusted Advisor Mindset – Ability to diagnose customer challenges, educate decision makers, and position DataStealth as the most effective solution.
You will partner with Sales Engineering, Product, and Marketing to win new logos and expand existing accounts.
Key Responsibilities:
1. Prospecting & Market Development
- Identify, research, and engage target accounts across financial services, healthcare, government, and other regulated sectors.
- Leverage your cybersecurity industry network to open doors with CISOs, IT Security Directors, and Compliance Leaders.
- Build and maintain a robust pipeline of qualified opportunities aligned with company growth targets.
2. Discovery & Solutioning
- Conduct deep discovery sessions with both technical and business stakeholders.
- Map customer pain points (data security, privacy, insider threats, compliance gaps) to specific DataStealth capabilities.
- Understand customer environments, including cloud, hybrid, and legacy systems, and position DataStealth’s integration advantages.
3. Technical Engagement
- Collaborate with Sales Engineering to design tailored demonstrations and proofs-of-concept.
- Articulate the technical differentiators of DataStealth: real-time protection, zero code changes, no data migration.
- Handle in-depth security and compliance objections with authority, drawing on your cybersecurity expertise.
4. Deal Management & Closing
- Lead the sales cycle from opportunity creation to contract signature.
- Navigate complex procurement processes, RFPs, legal reviews, and compliance assessments.
- Build consensus across multiple stakeholders (security, compliance, legal, procurement, and business units).
- Negotiate commercial terms while protecting deal value and margin.
5. Customer Advocacy & Relationship Building
- Act as a trusted advisor before, during, and after the sale.
- Build relationships that result in long-term partnerships, expansions, and renewals.
- Represent customer needs to Product and Engineering, influencing roadmap decisions.
6. Collaboration & Internal Alignment
- Partner with Marketing on campaigns, thought leadership, and industry events.
- Share field intelligence on competitors, customer challenges, and emerging trends.
- Contribute to the refinement of sales messaging, playbooks, and enablement content.
Qualifications:
Required
- 7+ years of enterprise sales experience in cybersecurity, data protection, or cloud security.
- Track record of closing $500K+ ACV enterprise deals with long sales cycles (6–18 months).
- Deep cybersecurity knowledge, with fluency in:
- Data security (encryption, masking, tokenization)
- Cloud and hybrid architectures
- Compliance frameworks (PCI, HIPAA, GDPR, SOC 2)
- Zero Trust and data loss prevention models
- Ability to engage credibly with CISOs, architects, and technical buyers.
- Strong understanding of regulated industries (finance, healthcare, government).
- Existing relationships with security and compliance decision makers is highly desirable.
- Exceptional communication skills: able to simplify complex technical concepts for both technical and executive audiences.
- Comfortable working in a fast-paced, startup environment with evolving priorities.
Preferred
- Experience at a cybersecurity startup or high-growth SaaS company.
- Background in consulting, security engineering, or solution architecture before moving into sales.
- Certifications such as CISSP, CISM, CISA, or cloud security certs (AWS, Azure, GCP).
Why Join DataStealth:
- Sell a unique, differentiated cybersecurity solution with proven enterprise adoption.
- Operate at the intersection of security, privacy, and compliance — one of the fastest-growing segments in technology.
- Join a high-growth, agile team where your impact is visible and valued.
- Competitive compensation: strong base salary, uncapped commission, health benefits
- Opportunity to become a thought leader in cybersecurity sales while building long-term customer relationships.
DataStealth is an equal opportunity employer. We encourage applications from candidates of all backgrounds and experiences.
We look forward to reviewing your application!
Top Skills
What We Do
DataStealth Discovers, Classifies, and Protects Sensitive Data and Documents.
DataStealth is the ultimate data-centric defense platform in the event of a malicious insider, perimeter, or endpoint compromise. Instead of relying on protecting your network perimeter, DataStealth protects the data and documents inside your network from attacks from both external and internal sources.
The patented DataStealth technology ensures that your sensitive data and documents are secure and adhere to all applicable privacy, regulatory, governance and compliance requirements.
