Head of Sales, Digital Native

AssemblyAI•San Francisco, CA

5d•$350,000 - $450,000•Hybrid

About The Position

AssemblyAI is seeking a Head of Sales, Digital Native to build and lead the sales organization for its fastest-growing business segment: digital native and AI-native companies building on voice. This role is responsible for scaling a small, high-performing team into a multi-layer organization, driving revenue growth across AssemblyAI's Voice AI models, orchestration services like the Voice Agent API, and LLM Gateway. This is a builder's role focused on owning hiring, organizational design, territory and account strategy, compensation plans, and operating cadence. The Head of Sales will personally recruit and develop front-line managers and ensure the sales team becomes productive quickly. The position reports to the VP of Customer Solutions and collaborates closely with Applied AI Engineering, Forward Deployed Engineering, Marketing, Engineering, and Research. The sales motion is technical, product-led, and evaluation-driven, focusing on engaging with builders early, building relationships, facilitating evaluations, and converting wins into production usage. AssemblyAI is a capital-efficient AI company with a proven business model and a steep growth trajectory. The company operates as a meritocracy, emphasizing lean operations, speed, and significant ownership for its employees. It processes over 2 million hours of audio daily and handles over 1 million API calls daily, serving thousands of customers. AssemblyAI is committed to diversity and equal opportunity, encouraging applications from individuals of all backgrounds.

Requirements

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, having hired and ramped 10+ reps and built the management layer underneath.
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 disrupting existing success.
Technical credibility, with comfort 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 desired behavior, and to run a reliable forecast.
A recruiting instinct, with a personal network, ability to close candidates, and a high bar under pressure.
High urgency and comfort with ambiguity, as the segment and its product lines are evolving rapidly.
Willingness to travel 50%+ of each month for customer visits, industry events, and team offsites.

Responsibilities

Build and lead the digital native sales organization, scaling from a small team of AEs and BDRs 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, including 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 key metrics.
Partner with Applied AI Engineering and Forward Deployed Engineering on the eval-to-production motion to convert technical wins 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 focused on pipeline creation 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 for new product launches.