Founding Account Executive

Cloaked • New York, NY

2d • $125,000 - $250,000 • Hybrid

About The Position

Cloaked is an AI Data Privacy startup dedicated to rebuilding consumer trust in how personal data is used. Our vision is to create an internet that serves the needs of its users, first and foremost—with individual privacy and opt-in at the core. Our product is a virtual “cloak” that you use as you visit any website — Facebook, Amazon, etc. It lets you choose to share all, some, or none of your private information based on your personal preference. About the role We’re looking for a Founding Account Executive to help build and scale our mid-market sales motion from the ground up. This role is ideal for a seller who thrives in early-stage environments and wants to play a key role in shaping how the company acquires customers. You’ll own the full sales cycle—from pipeline generation to close—while helping define the go-to-market playbook. This means not only closing deals but also helping establish repeatable processes for prospecting, discovery, demos, and pipeline development. The ideal candidate is both a closer and a builder: someone comfortable selling to security, engineering, and technical buyers while operating in the ambiguity of an early-stage company. You'll work closely with founders, product, and marketing to refine messaging, develop the ideal customer profile, and bring market feedback directly into the product and GTM strategy.

Requirements

• 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 Haves

• 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

Responsibilities

• 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 (LinkedIn, email, events, partnerships, etc.) 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

Benefits

• Cloaked employees have 401K, as well as top of the line Health, Dental, Vision and Life Insurance benefits.
• We offer flexible work arrangements and the ability to work remotely as needed.
• Cloaked provides a home office stipend in addition to a new company laptop (and other tech depending on the role).
• Competitive PTO: We encourage employees to take a minimum # of vacation per quarter. We see PTO as a preventative burnout measure and are committed to changing the industry standard.
• Monthly health stipend: Used for any kind of physical, mental or emotional care you’d like to take for yourself, be it a gym membership, a meditation app, or time with a personal trainer.
• Late Night Meals: We understand that sometimes work can get in the way of meal prep. In response to that, we offer employees a monthly meal stipend to be used when they don't have time to get a home cooked meal going!
• Professional Growth: Opportunities for career development and personal growth are provided to all employees who seek to further their knowledge and capabilities through an unlimited professional development fund. Additionally team members are encouraged to regularly attend conferences and industry events.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed