Head of Sales, Digital Native

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. We are one of the most capital-efficient AI companies on the planet - with under 100 people generating roughly $600K ARR per employee. With thousands of customers including Granola, Fireflies, Figure AI, and CallRail, the company has real scale. 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.

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'll report to the VP of Customer Solutions and work in tight partnership with Applied AI Engineering, Forward Deployed Engineering, Marketing, Engineering, and Research.

• 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.
• 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.
• 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.
• Represent the digital native voice of the customer to the leadership team and shape go-to-market strategy as new products launch.

• 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.
• 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.
• 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.
• 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.

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.