OffDeal

| The Role As a Full Stack Engineering Intern, you'll work directly with the M&A team to build the AI-native platform that empowers our investment bankers to be 10x more productive. Your work will directly impact how $10 trillion worth of small businesses change hands over the coming decade. What You'll Do Collaborate with our in-house investment bankers to own 0 to 1 projects, from ideation to deployment Build across the entire stack, in our 100% TypeScript (i.e. ReactJS + NodeJS) codebase Work with the latest AI tech, from on our in-house AI agents to complex recommendation and search algorithms We’re Looking for Someone Who Has / Is a… Proficiency in TypeScript, React, and NodeJS with experience building full-stack applications Bachelor's degree in Computer Science, Software Engineering, or related technical field, graduating within the next 24 months Previous software engineering experience through internships, co-ops, or professional roles Comfort in ambiguous and unstructured startup work environments Ability to relocate to NYC, to work in-person, 5 days a week Why Join OffDeal We only hire best-in-class engineers, and are offering compensation to reflect it Top-tier benefits, including medical, dental, vision, and unlimited PTO Free housing in NYC during your internship Perks like free food, Equinox membership, and NYC relocation stipend Work with bleeding edge AI on a modern codebase Opportunity to be a foundational team member at a well-funded, high-growth startup Be part of a mission to shape the future of small business ownership and to promote American entrepreneurship

| The Role As a Full Stack Engineer, you'll work directly with the CTO and the investment banking team to build the AI-native platform that empowers our investment bankers to be 10x more productive. Your work will directly impact how $10 trillion worth of small businesses change hands over the coming decade. What You'll Do Collaborate with our in-house investment bankers to own 0 to 1 projects, from ideation to deployment Build across the entire stack, in our 100% TypeScript (i.e. ReactJS + NodeJS) codebase Work with the latest AI tech, from on our in-house AI agents to complex recommendation and search algorithms We’re Looking for Someone Who Has / Is a… Proficiency in TypeScript, React, and Node.js with experience building full-stack applications Bachelor's degree in Computer Science, Software Engineering, or related technical field Previous software engineering experience through internships, co-ops, or professional roles Comfort in ambiguous and unstructured startup work environments Willingness to work in-person at our NYC office, 5 days a week Why Join OffDeal We only hire best-in-class engineers, and are offering compensation to reflect it Top-tier benefits, including medical, dental, vision, and unlimited PTO Perks like free food, Equinox membership, and NYC relocation allowance Work with bleeding edge AI on a modern codebase Opportunity to be a foundational team member at a well-funded, high-growth startup Be part of a mission to shape the future of small business ownership and to promote American entrepreneurship

| OffDeal is the world’s first AI-native investment bank for small businesses. Instead of selling AI to Goldman Sachs, we’re building what Goldman itself would have looked like if it launched in 2025. Wall Street's playbook works well, but only for billion-dollar deals - it breaks where most businesses actually exist. Traditional firms run oversized teams on outdated software, making smaller M&A transactions uneconomical. This leaves millions of small business owners with nowhere to turn for the most important sale of their lives… Until now. Our engineers built software to automate 80%+ of analyst work with AI, so our in-house bankers can focus where it counts - on earning owners’ trust and closing deals. We recently closed a $12M Series A ($17M in total funding) from Radical Ventures and Y Combinator and are scaling really fast. In less than a year, our team has already launched over 30 sell-side M&A transactions and has delivered numerous life-changing exits to our clients - and we’re just getting started. The Role As the Executive Assistant to OffDeal’s founders, you'll be the operational backbone of our growing team, wearing multiple hats to keep our fast-paced startup running smoothly. You'll work directly with the founders to manage everything from executive calendars to company culture, playing a critical role in scaling our operations as we transform the M&A industry. What You'll Do Manage day-to-day office operations including snacks, lunch logistics, non-technical procurement, and workspace maintenance Support recruiting logistics by scheduling interviews, coordinating travel, and processing payroll for the team Build company culture through team events, offsites, and fostering a positive work environment Handle financial operations including accounts payable, expense auditing, and basic bookkeeping Provide executive support by managing founder calendars, coordinating external events, and purchasing client gifts We're Looking for Someone Who Has / Is a… 3+ years of experience as an Executive Assistant, Office Manager, or similar role Exceptional organizational skills with the ability to juggle multiple priorities and deadlines Strong communication skills and professional demeanor Self-starter who thrives in ambiguous environments and can build processes from scratch High conscientiousness and meticulous attention to detail, ensuring nothing falls through the cracks Why Join OffDeal Opportunity to be a foundational team member at a well-funded, high-growth startup Competitive compensation and equity package Top-tier benefits, including medical, dental, vision, and unlimited PTO 401K Matching Perks like free food, Equinox membership, and NYC relocation allowance Work alongside exceptional talent in a collaborative, fast-paced environment Be part of a mission to shape the future of small business ownership and promote American entrepreneurship

| OffDeal is the world’s first AI-native investment bank for small businesses. Instead of selling AI to Goldman Sachs, we’re building what Goldman itself would have looked like if it launched in 2025. Wall Street's playbook works well, but only for billion-dollar deals - it breaks where most businesses actually exist. Traditional firms run oversized teams on outdated software, making smaller M&A transactions uneconomical. This leaves millions of small business owners with nowhere to turn for the most important sale of their lives… Until now. Our engineers built software to automate 80%+ of analyst work with AI, so our in-house bankers can focus where it counts - on earning owners’ trust and closing deals. We recently closed a $12M Series A ($17M in total funding) from Radical Ventures and Y Combinator and are scaling really fast. In less than a year, our team has already launched over 30 sell-side M&A transactions and has delivered numerous life-changing exits to our clients - and we’re just getting started. The Role Be the bandwidth‑multiplier for the CEO and the connective tissue across banking, BD, marketing, and product. Your North Star: surface the right problems, drive the right decisions, and ship the right projects - fast. If you’re a force of nature - slightly obsessed, high‑agency, and wired to bend reality in a startup’s favor—this seat is built for you. What You’ll Do Own the Operating Rhythm - Design and run quarterly planning, exec meetings, all‑hands, and board prep so everyone rows in the same direction. Make Metrics Meaningful - Decide which numbers truly move the needle, build dashboards, and keep the score visible company‑wide. Hunt Bottlenecks - Spot friction in workflows, tooling, or org design and drive the fix—process tweak, product change, or new hire. Run Special Projects - Spin up cross‑functional sprints with Sales, Marketing, Investment Banking, and Product to attack “CEO‑level” problems from idea to launch. Partner on Talent & Org Design - Shape head‑count plans, screen key candidates, and keep the culture tight as we double in size. Who We’re Looking For 4-8 years in top‑tier consulting, investment banking, BizOps, or prior CoS / operator role at a high‑growth startup. High-agency builder. You thrive in chaos, see ambiguity as opportunity, and execute without waiting for instructions. Elite communicator. Clear writer, concise speaker - comfortable from boardroom to hallway whiteboard. Low ego, high ownership. Happy to write strategy memos in the morning and comb through the data that afternoon. Hustle x IQ x EQ. Relentless drive, sharp analytical chops, and the empathy to bring others along. Data‑literate. Fluent in financial statements and funnel metrics; you believe arguments beat opinions when numbers back them up. Launch‑pad ambition. You view this role as a fast track to GM, COO, or founder. Why Join OffDeal Scope without ceilings. If it’s mission‑critical and unowned, it’s yours. Front‑row seat to company building. Shape strategy, org design, GTM motions, and investor narratives—simultaneously. Top‑tier benefits : medical, dental, vision, unlimited PTO, free meals, Equinox membership, 401K matching, and NYC relocation allowance. In‑person in NYC. Work side‑by‑side with founders and a team rewriting the playbook for a trillion‑dollar industry.

| OffDeal is the world’s first AI-native investment bank for small businesses. Instead of selling AI to Goldman Sachs, we’re building what Goldman itself would have looked like if it launched in 2025. Wall Street's playbook works well, but only for billion-dollar deals - it breaks where most businesses actually exist. Traditional firms run oversized teams on outdated software, making smaller M&A transactions uneconomical. This leaves millions of small business owners with nowhere to turn for the most important sale of their lives… Until now. Our engineers built software to automate 80%+ of analyst work with AI, so our in-house bankers can focus where it counts - on earning owners’ trust and closing deals. We recently closed a $12M Series A ($17M in total funding) from Radical Ventures and Y Combinator and are scaling really fast. In less than a year, our team has already launched over 30 sell-side M&A transactions and has delivered numerous life-changing exits to our clients - and we’re just getting started. The Role As a Staff Software Engineer, you'll be a technical lead on projects to build OffDeal’s AI-native platform, used by our in-house investment bankers. Your work will directly impact how $10 trillion worth of small businesses change hands over the coming decade. What You'll Do Collaborate with our M&A team to lead 0 to 1 projects, from technical design to deployment Drive technical strategy and architecture across our 100% TypeScript (i.e. ReactJS + NodeJS) codebase Proactively identify opportunities for new initiatives, and translate business needs into scalable solutions Lead cross-functional initiatives and influence product direction through technical expertise Establish engineering best practices, coding standards, and processes across the team Work with the bleeding edge of LLMs, from on our in-house AI agents to complex recommendation and search algorithms We’re Looking for Someone Who Has / Is a… 7+ years of software engineering experience in industry Demonstrated ability of shipping 0 to 1 products in TypeScript, React, and NodeJS Proven track record of technically leading complex projects and mentoring other engineers Comfort in ambiguous and unstructured startup work environments Generalist with a deep expertise in full-stack development and system design Strong product sense, being able to be their own product manager and designer Why Join OffDeal We only hire best-in-class engineers, and are offering compensation to reflect it Top-tier benefits, including medical, dental, vision, and unlimited PTO 401K Matching Perks like free food, Equinox membership, and NYC relocation allowance Work with bleeding edge AI on a modern codebase Opportunity to be a foundational team member at a well-funded, high-growth startup Be part of a mission to shape the future of small business ownership and to promote American entrepreneurship

| OffDeal is the world’s first AI-native investment bank for small businesses. Instead of selling AI to Goldman Sachs, we’re building what Goldman itself would have looked like if it launched in 2025. Wall Street's playbook works well, but only for billion-dollar deals - it breaks where most businesses actually exist. Traditional firms run oversized teams on outdated software, making smaller M&A transactions uneconomical. This leaves millions of small business owners with nowhere to turn for the most important sale of their lives… Until now. Our engineers built software to automate 80%+ of analyst work with AI, so our in-house bankers can focus where it counts - on earning owners’ trust and closing deals. We recently closed a $12M Series A ($17M in total funding) from Radical Ventures and Y Combinator and are scaling really fast. In less than a year, our team has already launched over 30 sell-side M&A transactions and has delivered numerous life-changing exits to our clients - and we’re just getting started. The Role As a Data Engineer, you'll be the architect of our data infrastructure, powering everything from AI-driven business valuations to strategic decision-making across the company, using data science. You'll work directly with our founders and cross-functional teams to build and maintain the data layer that enable our investment bankers to be 10x more productive. Your work will directly impact how we leverage data to transform the $10 trillion small business M&A market. What You'll Do Build and maintain our core data infrastructure including Looker dashboards, BigQuery data warehouse, and all data pipelines from external and internal tools Create product analytics dashboards that powers our business intelligence and lead generation efforts Conduct data readouts for experiments and perform ad-hoc analyses to drive strategic decisions Maintain and enhance OffDeal’s data lake by assessing new data vendors, cleaning and integrating external data sources, and improving accuracy of derived metrics using ML-based approaches Build the golden datasets needed for effective prompt experimentation and A/B testing of LLM-based workflows Improve search and ranking algorithms across all products Handle all Revenue Operations infrastructure, including CRM data models, data hygiene, and marketing attribution to ensure clean, actionable business metrics We're Looking for Someone Who Has / Is a… 3+ years of experience as a Data Engineer, Data Scientist, or similar role, at a technology company Proficiency in SQL and experience with machine learning frameworks for data quality and ranking improvements Experience working with a modern business intelligence data stack, especially BigQuery and Looker Familiarity with of CRMs, marketing attribution, and revenue operations workflows Experience with A/B testing frameworks and statistical analysis for product experimentation High conscientiousness and meticulous attention to detail, ensuring data accuracy and reliability across all systems Experience working with LLMs and prompt optimization is a plus Why Join OffDeal We only hire best-in-class engineers, and are offering compensation to reflect it Top-tier benefits, including medical, dental, vision, and unlimited PTO 401K Matching Perks like free food, Equinox membership, and NYC relocation allowance Work with bleeding edge AI on a modern codebase Opportunity to be a foundational team member at a well-funded, high-growth startup Be part of a mission to shape the future of small business ownership and to promote American entrepreneurship

| OffDeal is the world’s first AI-native investment bank for small businesses. Instead of selling AI to Goldman Sachs, we’re building what Goldman itself would have looked like if it launched in 2025. Wall Street's playbook works well, but only for billion-dollar deals - it breaks where most businesses actually exist. Traditional firms run oversized teams on outdated software, making smaller M&A transactions uneconomical. This leaves millions of small business owners with nowhere to turn for the most important sale of their lives… Until now. Our engineers built software to automate 80%+ of analyst work with AI, so our in-house bankers can focus where it counts - on earning owners’ trust and closing deals. We recently closed a $12M Series A ($17M in total funding) from Radical Ventures and Y Combinator and are scaling really fast. In less than a year, our team has already launched over 30 sell-side M&A transactions and has delivered numerous life-changing exits to our clients - and we’re just getting started. The Role As a Senior Software Engineer, you'll work directly with the CTO to build the AI-native platform that empowers our investment bankers to be 10x more productive. Your work will directly impact how $10 trillion worth of small businesses change hands over the coming decade. What You'll Do Collaborate with our in-house investment bankers to own 0 to 1 projects, from ideation to deployment Build across the entire stack, in our 100% TypeScript (i.e. ReactJS + NodeJS) codebase Work with the latest AI tech, from on our in-house AI agents to complex recommendation and search algorithms We’re Looking for Someone Who Has / Is a… 2+ years of work experience of shipping 0 to 1 products in TypeScript, React, and NodeJS Comfort in ambiguous and unstructured startup work environments Generalist with a love of building across the stack Strong product sense, being able to be their own product manager and designer Why Join OffDeal We only hire best-in-class engineers, and are offering compensation to reflect it Top-tier benefits, including medical, dental, vision, and unlimited PTO 401K Matching Perks like free food, Equinox membership, and NYC relocation allowance Work with bleeding edge AI on a modern codebase Opportunity to be a foundational team member at a well-funded, high-growth startup Be part of a mission to shape the future of small business ownership and to promote American entrepreneurship

| OffDeal is the world’s first AI-native investment bank for small businesses. Instead of selling AI to Goldman Sachs, we’re building what Goldman itself would have looked like if it launched in 2025. Wall Street's playbook works well, but only for billion-dollar deals - it breaks where most businesses actually exist. Traditional firms run oversized teams on outdated software, making smaller M&A transactions uneconomical. This leaves millions of small business owners with nowhere to turn for the most important sale of their lives… Until now. Our engineers built software to automate 80%+ of analyst work with AI, so our in-house bankers can focus where it counts - on earning owners’ trust and closing deals. We recently closed a $12M Series A ($17M in total funding) from Radical Ventures and Y Combinator and are scaling really fast. In less than a year, our team has already launched over 30 sell-side M&A transactions and has delivered numerous life-changing exits to our clients - and we’re just getting started. The Role As our Product Design Lead, you'll be a hybrid designer and product manager, owning the entire product experience from strategy to execution. You'll work directly with our founders to shape the user experience of our AI-native platform, driving growth through innovative lead generation, seamless external-facing portals, and strategic partnerships. Your work will directly impact how millions of small business owners discover and use our platform. What You'll Do Lead product management and design for external-facing tools for business owners, creating new acquisition channels and iterating on experiments to drive growth Own the product strategy and design for strategic partnership integrations and collaborative projects Design and enhance seller and buyer facing portals to maximize conversion and user satisfaction Monitor product analytics to identify UI/UX issues and develop data-driven solutions to improve user experience Create all visual assets including animations, marketing materials, and brand graphics across digital touchpoints Use Figma to craft designs for complex internal tools such as our in-house CRM We're Looking for Someone Who Has / Is a… 4+ years of combined experience in product management and design, preferably at high-growth startups or fintech companies Strong portfolio demonstrating end-to-end product design and successful product launches Proficiency in Figma and product analytics platforms Familiarity with AI-native design and prototyping tools Self-starter who can work independently and drive projects from conception to launch Excellent communication skills with the ability to present and defend design decisions to stakeholders Why Join OffDeal We only hire best-in-class builders, and are offering compensation to reflect it Top-tier benefits, including medical, dental, vision, and unlimited PTO 401K Matching Perks like free food, Equinox membership, and NYC relocation allowance Build products that lives on the bleeding edge of AI Opportunity to be a foundational team member at a well-funded, high-growth startup Be part of a mission to shape the future of small business ownership and to promote American entrepreneurship

| OffDeal is the world’s first AI-native investment bank for small businesses. Instead of selling AI to Goldman Sachs, we’re building what Goldman itself would have looked like if it launched in 2025. Wall Street's playbook works well, but only for billion-dollar deals - it breaks where most businesses actually exist. Traditional firms run oversized teams on outdated software, making smaller M&A transactions uneconomical. This leaves millions of small business owners with nowhere to turn for the most important sale of their lives… Until now. Our engineers built software to automate 80%+ of analyst work with AI, so our in-house bankers can focus where it counts - on earning owners’ trust and closing deals. We recently closed a $12M Series A ($17M in total funding) from Radical Ventures and Y Combinator and are scaling really fast. In less than a year, our team has already launched over 30 sell-side M&A transactions and has delivered numerous life-changing exits to our clients - and we’re just getting started. The Role As our Product Design Lead, you'll be a hybrid designer and product manager, owning the entire product experience from strategy to execution. You'll work directly with our founders to shape the user experience of our AI-native platform, driving growth through innovative lead generation, seamless external-facing portals, and strategic partnerships. Your work will directly impact how millions of small business owners discover and use our platform. What You'll Do Lead product management and design for external-facing tools for business owners, creating new acquisition channels and iterating on experiments to drive growth Own the product strategy and design for strategic partnership integrations and collaborative projects Design and enhance seller and buyer facing portals to maximize conversion and user satisfaction Monitor product analytics to identify UI/UX issues and develop data-driven solutions to improve user experience Create all visual assets including animations, marketing materials, and brand graphics across digital touchpoints Use Figma to craft designs for complex internal tools such as our in-house CRM We're Looking for Someone Who Has / Is a… 4+ years of combined experience in product management and design, preferably at high-growth startups or fintech companies Strong portfolio demonstrating end-to-end product design and successful product launches Proficiency in Figma and product analytics platforms Familiarity with AI-native design and prototyping tools Self-starter who can work independently and drive projects from conception to launch Excellent communication skills with the ability to present and defend design decisions to stakeholders Why Join OffDeal We only hire best-in-class builders, and are offering compensation to reflect it Top-tier benefits, including medical, dental, vision, and unlimited PTO 401K Matching Perks like free food, Equinox membership, and NYC relocation allowance Build products that lives on the bleeding edge of AI Opportunity to be a foundational team member at a well-funded, high-growth startup Be part of a mission to shape the future of small business ownership and to promote American entrepreneurship