Head of Sales, Digital Native

AssemblyAI•San Francisco, CA

5d•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 involves scaling a high-performing team into a multi-layer organization, driving revenue growth across AssemblyAI's Voice AI models, Voice Agent API, and LLM Gateway. This is a hands-on builder role responsible for hiring, org design, territory and target account strategy, compensation plans, and operational cadence. The Head of Sales will report to the VP of Customer Solutions and collaborate closely with Applied AI Engineering, Forward Deployed Engineering, Marketing, Engineering, and Research. The company's sales motion is technical, product-led, and evaluation-driven, focusing on early engagement with builders, relationship development, running evaluations, and converting wins into production usage. AssemblyAI is committed to diversity and equal opportunity, encouraging applications from all qualified individuals.

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 (hired and ramped 10+ reps and built the management layer).
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: carries own network, closes candidates, and holds a high bar under pressure to fill seats.
High urgency and comfort with ambiguity; the segment and its product lines are changing quickly and the playbook is being written as you scale.
Willingness to travel to drive impact (expect to be on the road 50%+ of each month).

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