Join our small but growing sales team and own the complete enterprise sales cycle for MyWorkDrive, a hybrid cloud file access solution. You'll be the technical expert who transforms IT directors' file access challenges into closed deals, working with Fortune 5000 companies to eliminate VPN dependencies while maintaining security and compliance.
This isn't a typical sales role, it's a technical leadership position where you'll architect solutions, run POCs, and close $5K-100K+ deals independently. Perfect for a solutions engineer ready to own revenue or an infrastructure expert wanting to transition to the vendor side.
What You'll Do
- Qualify enterprise opportunities through technical discovery
- Deliver compelling demos to IT directors, CISOs, and technical teams
- Design and manage proof-of-concepts that close in <30 days
- Navigate complex security reviews and procurement processes
- Close deals ranging from $5K-$100K ARR
- Master MyWorkDrive's architecture: AD/Entra integration, SSO, DLP, storage connectivity
- Assist in creating technical content and product improvements that shorten sales cycles
- Guide customers through implementations
- Ensure POC success metrics are met
- Orchestrate smooth handoffs to support post‑sale
- Identify expansion opportunities within accounts
What You Bring
Required Technical Knowledge
- 3+ years working with Active Directory, Azure AD/Entra ID, and SSO (SAML/ADFS)
- Deep understanding of Windows file shares, NTFS permissions, SMB protocol
- Experience with enterprise storage (on‑prem and cloud storage)
- Networking fundamentals (DNS, SSL, load balancers, firewalls)
- Comfort with PowerShell and basic scripting
Required Sales/Customer Skills
- Experience running enterprise POCs or implementations
- Ability to present complex technical concepts to executives
- Track record of managing multiple concurrent technical evaluations
- Consultative approach to problem‑solving
- Strong written communication for proposals and security documentation
Ideal Background (Any of These)
- Solutions Engineer at file sharing/storage company
- Senior role at MSP or VAR focused on infrastructure
- IT Manager/Director looking to move vendor‑side
- Infrastructure consultant with customer‑facing experience
Why MyWorkDrive
Immediate Impact : You join a small but fast team: every deal you close directly impacts our trajectory
Technical Depth : You will architect real solutions for complex environments
Career Growth : Clear path to Solutions Architect leadership or VP Sales as we scale
Economics : Competitive base + commission in a profitable, growing company
Culture : Remote‑first, low‑meeting culture focused on customer outcomes over activity metrics
The Product You'll Sell
MyWorkDrive enables secure file access without VPNs, keeping data on customers' existing storage while adding modern access methods. We serve 500+ enterprises including healthcare systems, financial services, and government agencies who need:
- Secure external file sharing with partners
- HIPAA/FINRA/GDPR compliance with full audit trails
- Zero‑trust file access replacing legacy VPNs
- Integration with existing AD/Azure infrastructure
Want to Apply?
Send your resume and a brief note explaining:
- Your most complex technical sale or implementation
- Why you want to move into (or stay in) technical sales
- Your experience with AD/Azure and enterprise infrastructure
Seniority level
- Mid‑Senior level
Employment type
- Full‑time
Job function
- Sales and Business Development
- Software Development