Upmarket Account Executive

The opportunity We are looking for an Upmarket Account Executive who thinks like a founder, sells like a closer, and operates with the rigor of someone who has won complex deals in competitive markets. You will own a named account territory of large enterprises, typically organizations with more than 2,000 employees, and be responsible for driving new logo acquisition and expansion revenue across your book. This is an outbound-first role. You will be expected to build pipeline from scratch, not wait for it. You will partner closely with SDRs, bring your own prospecting discipline, and run sophisticated multi-threaded sales cycles that involve economic buyers, IT, legal, and security stakeholders. You will represent Otter at the highest levels of enterprise selling, where your ability to build account plans, navigate organizations, and position AI value meaningfully will determine your results. Your impact Own a named enterprise territory and develop comprehensive account plans that map organizational structure, buying centers, executive relationships, and expansion pathways. Drive outbound prospecting alongside SDR partners to generate net new pipeline into target accounts, with a bias toward proactive territory development rather than inbound reliance. Run full-cycle enterprise sales from initial discovery through contract execution, managing multi-threaded relationships across VP and C-suite stakeholders. Close six and seven figure deals with discipline around deal qualification, mutual success plans, and forecasting accuracy. Partner with Customer Success to ensure seamless handoffs and identify expansion opportunities within installed accounts. Leverage AI-native tools and workflows to accelerate research, personalize outreach, build business cases, and manage your pipeline with precision. Represent the voice of the enterprise customer internally, contributing product feedback and market intelligence to help shape Otter roadmap priorities. Maintain a consistent cadence of activity and pipeline hygiene in Salesforce, ensuring forecast integrity and visibility for leadership. We're looking for someone who 5+ years of enterprise sales experience, with the majority of that time as an Account Executive carrying a quota against accounts of 2,000 or more employees. Documented history of closing multiple six-figure deals and at least one seven-figure transaction in a competitive market. Track record of building and sourcing your own pipeline, not just working inbound leads or SDR handoffs. Experience with complex, multi-stakeholder sales cycles involving security, legal, procurement, and executive approval. Skills and Approach Outbound-first mentality with strong prospecting instincts and the ability to break into cold accounts through creative, personalized approaches. AI-native and comfortable using tools like ChatGPT, Claude, or similar to accelerate research, improve messaging, and increase selling velocity. Strong account planning capability, including the ability to build territory maps, stakeholder influence maps, and multi-quarter engagement plans. Exceptional written and verbal communication with the executive presence to hold room with senior buyers. Collaborative operator who works well with SDRs, SEs, CS, and leadership without needing to be managed. Disciplined forecaster with intellectual honesty about deal stage and close probability. Nice to Have Prior experience selling AI, productivity, collaboration, or knowledge management software. Experience in a high-growth startup environment where process was still being built. Familiarity with MEDDIC, MEDDPICC, or a similar enterprise qualification methodology. About Otter.ai We are in the business of shaping the future of work. Our mission is to make conversations more valuable.With over 1B meetings transcribed, Otter.ai is the world’s leading tool for meeting transcription, summarization, and collaboration. Using artificial intelligence, Otter generates real-time automa