Upmarket Account Executive, Otter.ai

• 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

Desirable

• 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
• 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