Head of Sales, North America

Conversation. It’s the thread between our product and our people. The tool that enables us to forge relationships through compassion and expertise. To find the connection between our differences. It keeps us close together across borders and backgrounds and helps us create our shared vision.

Rasa means tight-knit. We get to the point and have the courage to ask ‘why?’. Because through relentless experimentation, passion, and vision, we’re transforming the way people interact with organizations through AI.

That’s Rasa. That’s our message.

Join us and add yours.

We’re looking for a senior sales leader to own and scale Rasa’s North American enterprise business. This role is responsible for driving revenue growth in our largest market by combining hands-on execution with team leadership. You will own the regional revenue number while actively engaging in complex enterprise deals, building and developing a high-performing team of Enterprise Account Executives, and leading long, multi-stakeholder sales cycles.

This role reports into the Chief Revenue Officer and plays a critical part in shaping how enterprises adopt Rasa’s technology.

The role is:

• Full-time, 100% Remote (with travel, as needed)

• Location: East Coast, USA

  • Rasa can not provide work sponsorship for USA-based positions.

You are a hands-on “player-coach” with a strong presence in the Deep Tech/Conversational AI space. You actively engage in the details of major enterprise deals. You have proven experience taking complex, innovative technologies, such as Generative AI, Voice, or CX Automation, and clearly connecting them to tangible business value for Fortune 500 organizations.

You will understand and communicate how Rasa can be used across multiple industries and then manage complex deal cycles. We’re a startup, so you’ll have to be comfortable rolling up your sleeves and doing whatever is required to support our mission. However, you can expect to:

• Own the North American revenue number, forecasting, and pipeline strategy.

• Recruit, train, and retain top-tier Enterprise AEs (hunters) who can navigate complex organizations.

• Move beyond transactional sales to strategic platform selling. Orchestrate 6-12 month sales cycles involving multiple stakeholders (CTO, CIO, VP of Customer Experience).

• Define and execute the "Land and Expand" strategy for the NA market, focusing on high-value verticals (Banking, Telecom, Hospitality, Healthcare).

• Partner closely with Marketing (Outbound strategy), Product, and Solutions Engineering (managing the technical win) to ensure deal velocity.

• Scale: You will be the primary driver for our largest market.

• Innovation: Sell a product that is at the forefront of the Generative AI revolution.

• Culture: Join a team of intelligent, driven professionals who are passionate about solving hard technical problems for the enterprise.

• 10+ years in Enterprise SaaS Sales, with 3-5+ years in a leadership role (VP, Head of Sales, or Sr. Director).

• Strong background in AI, Machine Learning, Customer Experience (CX), or Voice Technology. You understand the difference between a "chatbot" and "enterprise automation."

• Proven history of closing and guiding teams through $250k - $1M+ ARR deals.

• Deep ingrained knowledge of sales methodologies like MEDDIC, Challenger, or Command of the Message.

• You believe in building your own pipeline and empowering your team to use modern outbound techniques (familiarity with Outbound Squad or similar modern prospecting philosophies is a plus).

• Business or Technical degree; MBA is a plus.

This role sits within our Sales department, reporting into our Chief Revenue Officer. You will work with a team of 4-6 Account Executives and partnering with solutions engineers and business development representatives to build out your territory, progress opportunities through the buying journey and establish a partnership with key customers.

• Flexible hours and a dedicated remote budget

• A stipend for professional development & 6 paid education days to help you grow within your role

• Unlimited PTO + paid sick leave + paid public holidays

• A Macbook, and other tech to help you do your job

• We have regular remote team events, as well as an annual company-wide offsite

• Health benefits (USA only)

• 401(k) contribution with up to 4% match (USA only)

• Equity options

You can find more information about our benefits per location here: Rasa Perks & Benefits

Rasa is a leader in generative conversational AI, enabling enterprises to build and deliver next-level AI assistants. Merging a state-of-the-art engine with a user-friendly no-code UI, Rasa offers an open and adaptable platform that perfectly aligns with business logic. This innovative approach makes Rasa a reliable and trusted choice for enterprises seeking to enhance customer interactions while reducing costs. Rasa is privately held with funding from StepStone, PayPal, Accel, Andreessen Horowitz, Basis Set Ventures, and others. The company was founded in 2016 and is remote-first with a global presence.

Rasa is an equal opportunity employer. We are still a small team and are committed to growing inclusively. We want to augment our team with talented, compassionate people irrespective of race, color, religion, national origin, sex, physical or mental disability, or age.

You must be located in and a resident of the location(s) listed for us to proceed with your application.