Founding Account Executive

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. What We Offer Cloaked is a well-funded startup based out of NYC. Although we are a distributed team, the NYC team operates with a hybrid model. The office is located right off of Irving Street, one of New York’s most lively and iconic downtown corridors. We have a fully built out kitchen packed with drinks and snacks. The Cloaked team has diverse interests and so we frequently embark on team outings and go out for socials! Compensation And Benefits We offer above market rate pay and equity based off of the market's best commercially available data. Your compensation will be a combination of salary, bonus and equity. 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). Perks 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. We are really excited about having you join our mission-driven team and help us build the future of online privacy! We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us. 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. 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 strategiesIdentify 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 What skills and experiences will help you? 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 #J-18808-Ljbffr