Head of Sales - Obviously AI

Data Science problems are everywhere, but the talent is not. At Obviously AI, our vision is to turn every company into an AI company. We do this by providing businesses with access to world class, on-demand data science talent that helps them solve real business problems. On the back end, we empower data scientists with a set of internal groundbreaking tools to help them deliver results in minutes, not months.

We’re a small, scrappy group of people with a strong bent toward failing fast, bias for action and attention to detail. We’re focused on doing the best work of our lives and believe in having a healthy separation of work and life. We keep working hours flexible and are building a team with business teams located in San Francisco, CA and engineering teams located in Bangalore, India.

Obviously AI is backed by some of the top venture capital firms in the US, and you’ll be on the ground floor of a fast-growing company with a big mission.

About You

As a Head of Sales at Obviously AI, you will be responsible for both tactical and strategic work like leading our sales team, hiring key sales roles, optimizing our sales operations and building & executing sales strategies. You will also be responsible for overall business revenue and should be willing to get your hands dirty with everyday sales tasks as and when required. You will have no shortage of exciting opportunities in the pipeline and you will constantly find yourself strategizing ways to move them along rapidly.

Our ideal candidate for this role is someone who is a hands-on leader with a proven track record in sales and sales management, (especially in the startup environment), has extremely high agency and is very proactive in taking initiative, and can understand how large companies buy along with having extensive knowledge of different sales methodologies. You also have extensive experience in AI/ML, Analytics or related fields, a passion for innovation, and the ability to mentor and guide a high-performing sales team. You'll report directly to the founders, you'll be a key proponent of Obviously AI’s early success and have the equity (aka. "skin in the game") to make it worthwhile.

• Sales Leadership & Mentorship
• Act as a mentor and go-to resource for the sales team, providing guidance and support to achieve sales targets.
• Foster a culture of continuous improvement, high performance, and accountability within the team.
• Advocate and hold Sales Development Representatives (SDRs) accountable to hit activity metrics and qualified opportunity quotas.
• Sales Execution
• Step in to qualify and close deals as needed, leveraging extensive experience as an Account Executive (AE).
• Ensure the team meets and exceeds their sales quotas through effective management and support.
• Sales Strategy
• Develop and implement innovative sales strategies to overcome challenges and achieve quarterly and annual sales goals.
• Collaborate with cross-functional teams, including marketing and support, to align sales efforts with overall business objectives.
• Sales Operations
• Define and document sales processes and best practices to ensure efficiency and consistency.
• Monitor and maintain sales hygiene in the CRM system, ensuring accurate and timely updates.

Responsibilities

• Collaborate with SDRs & AEs to build strategic roadmaps for closing opportunities on a weekly basis.
• Develop quarterly sales strategies and ensure their execution.
• Offer coaching and guidance on sales calls, providing real-time feedback and support.
• Ensure CRM hygiene and consistency in updating sales activities and pipeline status.
• Align with Customer Success (CS) to develop revenue expansion plans.
• Brainstorm with sales and marketing teams for new content and campaign ideas.
• Identify and provide training resources on relevant AI trends and technologies.
• Report on new leads, sales activities, pipeline status, and revenue metrics.
• Ensure timely follow-ups on all sales activities and leads.
• Drive team morale and maintain alignment with the company’s big-picture strategy.
• Communicate customer and prospect feedback to the product team for continuous improvement.
• Serve as the point of escalation for high-value deals, providing strategic support to AEs.

Requirements

• Deep understanding and genuine interest in AI/ML technologies.
• At least 10 years of experience in sales, with a minimum of 4 years in a sales management role.
• Proven experience in growing sales teams within startup environments (Series A - C preferred).
• Demonstrated success in defining and standardizing sales operations and setting up CRM systems.
• Experience as an Enterprise AE with a track record of closing complex deals.
• Ability to work cross-functionally with product, marketing, and customer success teams.
• Strong strategic thinking and problem-solving skills.
• Excellent communication, negotiation, and interpersonal skills.
• Ability to work out of our San Francisco office 3 days a week.

Benefits

• Health Care Plan
• Paid Time Off (Vacation, Sick & Public Holidays)
• Work Equipment
• Stock Option Plan
• Training & Development
• Hybrid Work: 3 days a week in our San Francisco office