Founding Sales Development Representative

About Keyway Keyway builds agentic infrastructure purpose-built for commercial real estate. Our AI-native platform connects data, documents, and workflows across the CRE lifecycle, turning fragmented information into trusted, actionable intelligence. Our solutions adapt to how each customer works, with flexible workflows, enterprise-grade security, and private environments. Based in New York, Keyway works with leading real estate firms across the U.S. and internationally. We’re building a culture where people take ownership, different perspectives are heard, and thoughtful execution matters. We believe AI should amplify—not replace—CRE expertise, taking on manual tasks so teams can focus on judgment, decisions, and higher-value work. About the role We are looking for a Founding Sales Development Representative to help build Keyway's outbound engine from the ground up. This is not a high-volume, script-led SDR role. You will research target accounts, develop a point of view on their business, create personalized outreach, and start relevant conversations with senior commercial real estate leaders in the U.S. Your work will directly shape how Keyway builds pipeline, positions its products, and learns from the market. You will partner closely with Sales and Marketing in a consultative, longer-cycle sales motion, typically three to six months, turning well-researched outreach into qualified meetings and real opportunities. As an early commercial hire in this function, you will have meaningful ownership over the process, messaging, tools, and experiments that make the motion work. What your day would look like Build targeted account plans: Research commercial real estate firms, map relevant stakeholders, and prioritize accounts based on fit, potential, and timing. Create personalized outbound: Develop thoughtful email, LinkedIn, phone, and other outreach tailored to each prospect's business, priorities, and likely pain points. Generate qualified pipeline: Engage decision-makers, run first conversations, qualify opportunities, and book high-quality meetings for the Sales team. Lead discovery with curiosity: Ask strong questions to understand a prospect's current workflow, priorities, challenges, and buying context—then communicate where Keyway may be able to help. Own the follow-up: Nurture prospects who are not ready to engage immediately with relevant, consistent follow-up and clear next steps. Build the operating system: Help establish the CRM hygiene, qualification criteria, outreach cadences, reporting, and handoffs that will become Keyway's SDR playbook. Experiment and improve: Test messaging, channels, sequences, and account segments; use results to improve conversion and share market insights with Sales, Marketing, and Product. Collaborate across teams: Work closely with Sales and Marketing to align campaigns, refine positioning, prepare meetings, and ensure a strong prospect experience from the first touchpoint. What success looks like You consistently create qualified conversations and pipeline within our target accounts. Sales receives well-prepared meetings with clear prospect context, pain points, and next steps. Outreach becomes more effective over time because you turn data and prospect feedback into better messages and processes. You help create a repeatable outbound playbook that Keyway can scale as the commercial team grows. What we're looking for 3+ years of experience in outbound SDR, BDR, or a similar pipeline-generation role in B2B SaaS or a consultative sales environment. Demonstrated ability to research accounts, personalize outreach, and engage senior decision-makers—not simply run high-volume sequences. Strong discovery, communication, and relationship-building skills, with the confidence to pick up the phone and start a thoughtful conversation. A builder mindset: you are comfortable operating with ambiguity, testing ideas, and creating structure where it does not yet exist. Highly organized and disciplined with follow-up, prioritization, CRM management, and time management. Analytical and data-informed; you can use funnel results to identify what is working and what needs to change. Resilience, curiosity, and a genuine interest in learning how customers make decisions. Experience selling into commercial real estate, financial services, or another complex B2B market is a plus, but not required. Experience with CRM, sales engagement, and prospecting tools is also a plus. Why Keyway Be the founding SDR and have a real hand in building Keyway's commercial engine. Work on a complex, high-impact product at the intersection of AI and commercial real estate. Partner directly with experienced Sales, Marketing, Product, and Customer teams in a collaborative environment. Join a distributed team that values ownership, learning, and doing great work together. Location This is a hybrid full-time role based in New York City. Compensation The base salary for this role is $70,000, with on-target earnings (OTE) of $90,000, inclusive of base salary and variable commission. Equal opportunity Keyway is an equal opportunity employer. We are committed to building an inclusive team and welcome qualified applicants of all backgrounds. AI in our hiring process Keyway may use AI-enabled tools to support certain stages of our hiring process, including the review of job applications and role-related materials. These tools help our hiring team evaluate applications more efficiently and consistently; they do not make hiring decisions on their own. All employment decisions are made by Keyway's hiring team.