Senior Director of Sales

The Opportunity Otter.ai is looking for a dynamic, hands-on Senior Director of Sales to help build and scale our sales organization through its next phase of growth. This is a build opportunity for an experienced sales leader who thrives in a fast-paced environment and enjoys creating structure, developing talent, and driving results. You'll lead a team of Sales managers and individual contributors, with the opportunity to shape the team's structure, scalable processes, and raise the bar for sales execution. We're looking for a leader who can operate both strategically and tactically — someone equally comfortable developing sales leaders, building a high-performing organization, and rolling up their sleeves to coach deals, improve execution, and accelerate revenue growth. This role follows a hybrid work schedule, with three days per week in one of our Bay Area offices. What You'll Do • Scale the sales organization, establishing the operating rhythms needed to support sustainable revenue growth. • Lead and develop Sales managers and individual contributors, building leadership capability, strengthening accountability, and creating a culture of high performance. • Own sales execution and performance across the team, driving consistent quota attainment, pipeline generation, and revenue growth. • Assess organizational capabilities, identify talent gaps, and help shape hiring, team structure, and future leadership needs. • Establish clear performance expectations, KPIs, forecasting discipline, and accountability across the organization. • Develop and execute effective outbound sales strategies to drive pipeline creation and new business opportunities. • Take a hands-on approach to coaching, including joining customer calls, reviewing deals, strengthening negotiation strategies, and improving sales execution. • Build scalable onboarding, training, and enablement programs that accelerate ramp time and improve sales productivity. • Implement and reinforce effective sales methodologies, including MEDDPIC, to improve qualification, pipeline quality, and deal execution. • Partner closely with Marketing, Customer Success, Solutions Engineering, Product, and other cross-functional leaders to strengthen go-to-market execution. • Leverage Salesforce and sales performance data to improve visibility, operational efficiency, and forecast accuracy. What You Bring • 10+ years of progressive sales experience, including significant experience leading and scaling high-performing sales teams. • Proven experience leading both Sales managers and individual contributors, with a track record of developing future leaders. • Demonstrated success building or transforming sales organizations, ideally in a high-growth SaaS or technology environment. • Strong track record of consistently delivering revenue growth and exceeding sales targets. • Experience building successful outbound sales motions and scalable pipeline generation programs. • Deep understanding of sales execution, forecasting, pipeline management, and methodologies such as MEDDPIC. • Strong coaching instincts and a willingness to get directly involved in deals, customer conversations, and team development. • Experience recruiting, developing, and retaining high-performing sales talent. • Highly analytical, with the ability to translate performance data into clear priorities and actionable improvements. • A builder's mindset — resourceful, adaptable, comfortable with ambiguity, and energized by the opportunity to create rather than inherit. • Strong communication skills, and the ability to partner cross functionally. 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,