Head of Sales, Digital Native

Why AssemblyAI AssemblyAI builds the best-in-class Voice AI models powering the next generation of voice applications. Our models serve 600M+ inference calls monthly, process 1M+ hours of audio daily, and power 2 billion+ end-user experiences. The Voice AI space is at an inflection point; we’re looking for folks truly excited to join a small team and help define the future of the industry. We are one of the most capital-efficient AI companies on the planet - with under 100 people generating roughly $600K ARR per employee, we sit among the top 5 most revenue-dense teams within the fastest-growing AI companies today. That's not an accident; it's a deliberate choice to stay lean, move fast, and give every person on the team outsized ownership and impact. With thousands of customers including Granola, Fireflies, Figure AI, and CallRail, the company has real scale - processing over 2 million hours of audio daily and handling more than 1 million API calls every day. This is a rare growth-stage opportunity where the business is proven and the trajectory is steep, but the team is still small enough that your fingerprints are on everything. If you've ever felt buried under layers of bureaucracy, starved of real ownership, or frustrated watching your work disappear into a slow-moving org, AssemblyAI is built differently. The company operates as a true meritocracy, with no heavy planning or approval processes and no gatekeeping on the tools or information you need. For anyone who genuinely cares about voice AI, not as a trend to chase, but as a technology to build, this is the place where the most interesting problems at the most interesting scale are being solved by a team small enough that you'll actually know everyone's name. We’re committed to creating a space where our employees can bring their full selves to work and have equal opportunity to succeed. No matter your race, gender identity or expression, sexual orientation, religion, origin, ability, age, veteran status, if joining this mission speaks to you, we encourage you to apply! About the role: We're looking for a Head of Sales, Digital Native to build and lead the sales organization covering the fastest-growing segment of our business: digital native and AI-native companies building on voice. Today this is a small, high-performing team selling into a targeted list of the best accounts building with voice. You will scale it into a multi-layer organization of Account Executives and the front-line managers who lead them, while growing revenue across AssemblyAI's Voice AI models, orchestration like our Voice Agent API, and LLM Gateway. This is a builder's role, not a caretaker's. You will own the hiring bar, the org design, the territory and target account model, the comp plans, and the operating cadence for the segment. You will personally recruit and develop the first wave of front-line managers, and you'll be accountable for making a scaling AE org productive fast - not just filling seats. You'll report to the VP of Customer Solutions and work in tight partnership with Applied AI Engineering, Forward Deployed Engineering, Marketing, Engineering, and Research. Our motion is technical, product-led, and evaluation-driven: customers choose us because we win benchmarks and ship the best customer experience. Your team's job is to get in front of the right builders early, build relationships, get them to run an evals, and convert wins into production usage that compounds. What You'll Do: Build and lead the digital native sales organization - scaling from a small team of AEs and BDRs today to a larger sales org within the next year Own the land number for the segment, focusing on bringing in net new customers and helping them scale up their usage in production Hire, onboard, and develop front-line managers; establish the bar, the interview loop, and the ramp plan that make new AEs productive in weeks rather than quarters Design the segment's coverage model - territories, target account tiers, and specialization across a large digital native account list where every company has a real production voice use case Build the operating system for the team: forecasting, pipeline inspection, deal reviews, quota and comp design, and the metrics that tell you early whether the org is on track Partner with Applied AI Engineering and Forward Deployed Engineering on the eval-to-production motion, so technical wins convert into deployed, growing usage Work with Engineering, Research, and Marketing to shorten the time from product launch to real revenue Drive an outbound-first culture where pipeline is created, not waited for, and where outreach earns replies through custom benchmarks, competitive insight, and use-case-specific demos Represent the digital native voice of the customer to the leadership team and shape go-to-market strategy as new products launch What You'll Need: 8+ years in technical sales with 4+ years leading sales teams, including experience managing managers A track record of scaling a sales org through a step change in headcount - you have hired and ramped 10+ reps and built the management layer underneath you, not inherited it Experience selling infrastructure, APIs, or developer platforms to engineering and product buyers; ideally in a usage-based or consumption pricing model Fluency with a product-led, bottoms-up motion that layers a sales team on top of self-serve adoption without breaking what already works Technical credibility - comfortable discussing API architectures, model accuracy tradeoffs, latency, and deployment options directly with engineers and CTOs Demonstrated ability to design territories, quotas, and comp plans that drive the right behavior, and to run a forecast leadership can rely on A recruiting instinct - you carry your own network, you close candidates, and you hold a high bar under pressure to fill seats High urgency and comfort with ambiguity; this segment and its product lines are changing quickly and the playbook is being written as you scale A willingness to travel to drive impact - expect to be on the road 50%+ of each month for customer visits, industry events, and team offsites Pay Transparency: AssemblyAI strives to recruit and retain exceptional talent from diverse backgrounds while ensuring pay equity across our team. Our salary ranges are set to be competitive for our size, stage, and industry, and reflect just one component of the full compensation, benefits, and rewards we offer. Salary determinations consider a variety of factors, including relevant experience, technical depth, skills demonstrated during the interview process, and maintaining internal equity with peers on the team. The range shared below represents a general expectation for the posted position. However, we are open to considering candidates who may fall above or below the outlined experience level—in those cases, we will communicate any adjustments to the expected salary range. The range provided applies to candidates located in the United States. For candidates outside of the U.S., compensation ranges may differ; any adjustments will be communicated throughout the interview process. Compensation: $350,000–$450,000 in on-target earnings (OTE) The expected total compensation for this role is listed above (including base salary and commission). Our total compensation package includes competitive equity grants, 100% employer-paid benefits, and working alongside the team in our San Francisco or New York City office. A 401k match up to 4% is offered to all US-based full time team members. AI to Interview: If you’re selected for an interview, please review this resource to better understand how AssemblyAI approaches the use of AI in our interview process. GDPR privacy notice: Candidates from the EU should review this job applicant privacy notice before applying. Keep Exploring AssemblyAI: Speech-to-text | Streaming speech-to-text | Speech Understanding | LLM Gateway Try the Playground Our $50M Series C fundraise Check us out on YouTube!