Founding Account Executive
Most applications go out cold — see where you stand first. No sign-up to start.
Don't just apply. Show up ready.
Olive works from this exact posting — no sign-up to start.
At a glance
Job overview
Pensive is hiring a Founding Account Executive. Pensive is seeking a Founding Account Executive to drive the adoption of its AI grading and tutoring platform in higher education. This role involves working closely with founders and product teams to define sales strategies, engage with universities, and manage the full sales cycle from inbound leads to institutional rollouts. The ideal candidate is ownership-oriented, AI-native in their workflow, and passionate about technology's role in amplifying human judgment in education.
Key focus areas include Convert high-intent inbound users into paying customers, Proactively research and outbound into new opportunities, and Run compelling product demos.
Successful candidates bring 5+ Years Closing Experience, Consistently Hit Or Exceeded Quota, and AI-Native. Important skills include Automate Research Using AI Tools, Automate Outreach Using AI Tools, Automate Follow-ups Using AI Tools, Automate Deal Management Using AI Tools, Operating With Ambiguity, and Building Process From Scratch. Preferred (not required): Product Demos, Articulating Value, Navigate Higher-Ed Sales Cycles, and Onboard New Customers.
Skills & qualifications
Skills
Qualifications
Full job description
About Pensive Please check our Notion doc to learn more about our mission, founders, and culture.
About the Role We’re looking for a Founding Account Executive to bring our market-leading AI grading and tutoring platform to higher-education institutions around the world.
Higher ed is undergoing a once-in-a-generation shift. AI is changing how students learn, how instructors teach, and how institutions operate. We’re building the system that sits at the center of that transformation. We’re looking for an AE who wants to help define this category from day one.
This is an early, high-ownership role. You’ll work directly with founders, product, and customers to shape how we sell, who we sell to, and how we win.
Who You Are
-
You have 5+ years of closing experience at a software company.
-
You have consistently hit or exceeded quota and can point to concrete wins.
-
You’re deeply ownership-oriented: you do more than what’s “enough” and surprise your team with your output.
-
You’re AI-native in how you work . You actively automate research, outreach, follow-ups, and deal management using AI tools. Other reps ask you how you move so fast.
-
You’re comfortable operating with ambiguity and enjoy building process from scratch.
-
You care about education and believe technology should amplify human judgment , not replace it.
What You’ll Do
-
Convert high-intent inbound users (professors, TAs, departments) into paying customers.
-
Proactively research and outbound into new opportunities across universities and institutions.
-
Run compelling product demos , clearly articulating value to different stakeholders.
-
Navigate complex higher-ed sales cycles by distinguishing between end users, buyers, and decision-makers.
-
Close deals ranging from single-course pilots to larger institutional rollouts .
-
Onboard new customers and handle early-stage support and FAQs.
-
Act as the voice of the customer , feeding insights directly into product and roadmap discussions.
You've read the whole posting — now see how you match it.