Head of Sales

This is a fully remote position, open to applicants in United States.

📋 Description

• Oversee the Account Executive and Sales Engineering teams.

• Establish the Sales strategy, objectives, metrics, operational rhythms, headcount plans, budget, organizational structure, executive communication, and performance benchmarks.

• Create a multifaceted Sales system that encompasses strategic, mid-market, product-led, outbound, partner, and regional opportunities.

• Design targeted account and outbound initiatives based on customer insights, use cases, market trends, and product signals.

• Ensure that high-potential product usage, sign-ups, inbound inquiries, support interactions, and target-account signals are assigned a dedicated owner with a defined next step.

• Grow the Sales team by recruiting and nurturing outstanding talent.

• Engage in customer discussions weekly and lead or assist with complex opportunities.

• Establish valuable forecasting definitions and review practices.

• Define effective collaboration across Customer Growth, Partnerships, Marketing, Finance, Revenue Operations, Product, Engineering, TAM, and Support.

• Transform discovery patterns, objections, migrations, successes, and failures into playbooks, reusable resources, product evidence, and team training.

• Facilitate increased revenue for more applications without turning Sales into a generic “spray and pray” operation.

⛳️ Requirements

• Over 5 years of experience leading Sales in a technically intricate B2B setting.

• Experience managing managers or senior team leaders along with individual contributors.

• Proven success across various sales motions, including strategic enterprise, mid-market, product-led Sales support, targeted outbound, channel, or regional selling.

• Experience in generating a qualified pipeline rather than relying solely on inbound demand or a large SDR team.

• Adequate product and technical knowledge to discuss potential migrations with Engineering.

• Proficiency in pipeline inspection, forecasting, conversion metrics, capacity planning, and performance management.

• Demonstrated ability in hiring, coaching, developing leaders, elevating standards, and making tough talent decisions.

• Strong collaborative skills with Product, Engineering, Marketing, Finance, Operations, Partnerships, and post-sale teams.

• Commitment to staying actively involved with customers and participating in commercial activities.

• Ideally, experience in a product-led or usage-based business model.

• Ideally, familiarity with app infrastructure, payments, monetization, developer platforms, or other domains with significant implementation complexity.

• Ideally, experience fostering a partnership between Account Executives and Sales Engineering.

• Ideally, experience with partner-sourced, international, or regional initiatives.

• Ideally, experience selling to purchasing groups including engineering, product, growth, finance, security, legal, and procurement.

🏝️ Benefits

• Competitive equity in a rapidly growing, Series C startup supported by premier investors, including Y Combinator.

• A 10-year window to exercise vested equity options.

• Fully remote and flexible working conditions.

• 4-5 weeks of recommended annual time off for mental, physical, and emotional rejuvenation.

• $2,000 USD workspace setup allowance.

• $1,000 USD yearly stipend for ongoing education.