Founding Account Executive
Cloaked, Inc., New York, NY, United States
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—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.
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 (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
What we offer Cloaked is a well‑funded Series‑B 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.
Cloaked employees have 401(k), 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).
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.
Perks
Competitive PTO: We encourage employees to take a minimum number 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!
#J-18808-Ljbffr
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 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
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
What we offer Cloaked is a well‑funded Series‑B 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.
Cloaked employees have 401(k), 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).
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.
Perks
Competitive PTO: We encourage employees to take a minimum number 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!
#J-18808-Ljbffr