Cloaked-app is hiring a Founding Account Executive to build and scale our mid-market sales motion from the ground up. This is a foundational role for a seller who thrives in early-stage environments and wants to shape how we acquire customers. You'll own the full cycle—from pipeline generation to close—while helping define the go-to-market playbook.
What You'll Do
- Manage deals from initial prospecting through close.
- Lead discovery conversations with security, engineering, and technical stakeholders.
- Run consultative demos that connect product capabilities to real customer pain.
- Guide buyers through evaluation and procurement.
- Build and execute outbound prospecting strategies.
- Identify and prioritize target accounts aligned with the Ideal Customer Profile.
- Develop messaging that resonates with security, IT, and developer-adjacent buyers.
- Use multi-channel outreach to generate pipeline.
- Help define the early GTM playbook and sales motion.
- Refine messaging, qualification frameworks, and discovery practices.
- Share customer insights that influence product direction and positioning.
- Partner closely with founders and leadership on strategy and market feedback.
- Lead structured discovery to uncover pain, urgency, and business impact.
- Translate product capabilities into clear business value for customers.
What We're Looking For
- 5–8 years of SaaS sales experience, preferably in mid-market environments.
- Proven track record hitting $500K–$2M+ annual quota.
- Experience managing $10K–$100K ACV deals with sales cycles around 30–60 days.
- Strong ability to self-generate pipeline through outbound prospecting.
- Experience selling to security, engineering, or technical buyers.
- Excellent discovery and consultative selling skills.
- Ability to translate complex products into clear business value.
- Comfortable operating in early-stage startup environments with ambiguity.
- Strong ownership mindset and ability to take initiative without a defined playbook.
Nice to Have
- Experience selling security, identity, privacy, or developer-focused products.
- Previous experience at Series A or Series B startups.
- Existing network or relationships with security, engineering, or IT buyers.
- Experience helping build sales processes, messaging, or GTM strategy from scratch.
- A strong “builder” mindset—someone who enjoys creating systems and playbooks, not just executing them.
Team & Environment
You will work closely with founders, product, and marketing.
Benefits & Compensation
- 401K.
- Top of the line Health, Dental, Vision and Life Insurance benefits.
- Flexible work arrangements and the ability to work remotely as needed.
- Home office stipend.
- New company laptop.
- Competitive PTO with a minimum number of vacation days per quarter.
- Monthly health stipend for physical, mental, or emotional care.
- Monthly meal stipend for late nights.
- Unlimited professional development fund for career development and personal growth.
- Encouragement to attend conferences and industry events.
- Above market rate pay.
- Equity based on the market's best commercially available data.
Work Mode
This is a hybrid position. You will be based in NYC.
Cloaked-app is a mission-driven team building the future of online privacy. Our team has diverse interests and frequently embarks on team outings and socials. We are committed to changing the industry standard on burnout and PTO.
