Enterprise Account Executive

Sales | Enterprise Account Executive San Francisco, CA | Full-Time 

Position Overview 

We are seeking an experienced Enterprise Account Executive to join our sales team. In this role, you will lead strategic enterprise deals with carriers and logistics companies. You will build deep customer relationships, run investigative discovery, and guide prospects through complex buying processes from first conversation to close. The ideal candidate has scaled through a large enterprise software company and brought that rigor into a startup environment — they know how to be resourceful, self-sufficient, and creative when there's no playbook to follow. This role is based in San Francisco. 

Key Responsibilities 

Discovery & Strategic Selling 

• Lead the full sales cycle for enterprise customers from discovery through close. 

• Run deep, layered discovery conversations that uncover how the business actually runs, where workflows break, and what the real operational and financial pain is — always asking why, and then asking again. 

• Demonstrate genuine curiosity: follow threads deeply, ask uncomfortable questions, and resist pitching until the real pain surfaces. 

• Recognize patterns across deals and adapt in real time when sales cycles don't follow a clean playbook. 

Enterprise Deal Execution 

• Navigate multi-person buying processes and tailor messaging to each stakeholder — operators, managers, and executives. 

• Identify blockers before they surface and work around them creatively, thinking strategically about deal structure, ROI, and long-term implications. 

• Maintain strong deal hygiene including notes, follow-ups, and clear next steps — keeping deals moving through disciplined process ownership. 

• Handle objections around price, timing, and vendor switching using a repeatable, structured system that converts resistance into a path toward yes. 

Relationship Building & Industry Credibility 

• Build trusted relationships with operators, managers, and executives within carrier organizations — including entertaining clients and deepening relationships over time. 

• Leverage deep industry knowledge to earn instant credibility in first meetings and speak fluently to the workflows carriers experience. 

• Adapt communication style to different personalities and roles across complex organizations. 

Ownership & Accountability 

• Reflect honestly on lost deals, take full ownership of outcomes, and use those lessons to sharpen approach — no excuses, just adjustments.

• Move quickly, push deals forward, and take initiative rather than waiting for direction. • Communicate ideas, value, and next steps clearly and concisely for both customers and internal teams. 

Channel & Strategic Influence 

• Help identify and source new channels or partnership paths that could create additional pipeline. 

• Bring market feedback to leadership in a structured, consistent way — patterns that influence product, roadmap, and positioning, not just anecdotes. 

• Use modern sales tools and AI as a core part of your workflow — not just a productivity layer — to operate faster than traditional sales motions. 

Help Define Our Sales Motion 

We're an early team, and your work will directly shape how our GTM function operates and succeeds. You won't be handed a playbook — you'll help write it. That means bringing structure where there isn't any, surfacing what's working and what isn't, and thinking beyond your own quota to the health of the broader sales org. 

Core Competencies 

The following competencies define what great looks like in this role: 

Curiosity / Strategic Discovery: Asks real strategic enterprise questions that uncover how the business runs, where workflows break, and what the true pain is. Digs deeper from a place of genuine curiosity — follows threads and keeps asking "why." 

Enterprise Sales Cycle Execution: Identifies blockers before they arise and works around them creatively, thinking strategically about deal structure, ROI, and long-term implications. 

Sales IQ: Recognizes patterns across deals, adapts to unclear or non-linear sales cycles, and navigates ambiguity with confidence. 

Ownership & Accountability: Looks back on deals lost with honesty, takes full accountability for outcomes, and uses those lessons to continuously sharpen approach. 

Relationship Building: Builds genuine rapport across different personalities, earns trust quickly, and deepens client relationships over time — including through in-person meetings and client entertainment. 

Objection Handling System: Has a repeatable, structured approach to turning every objection into a path toward yes. 

Industry Credibility: Brings industry knowledge or background that earns instant trust and enables credible conversations about carrier and logistics workflows. 

Multi-Person Deal Navigation: Strategically adapts messaging and approach for each individual across the buying committee, from frontline operators to the C-suite. 

Deal Control & Hygiene: Keeps deals moving with clear next steps, strong notes, diligent follow-ups, and disciplined process execution. 

Channel Awareness: Proactively identifies new channel or partnership opportunities that expand pipeline beyond direct outbound.

Strategic Internal Influence: Surfaces market feedback to product and leadership in a structured way — patterns and insights that shape roadmap and positioning. 

Leverages Tools & Technology: Uses modern sales tools and AI to make their workflow meaningfully faster and more efficient than traditional motions. 

Clear, Concise Communication: Communicates value, ideas, and next steps in a way that is easy for both customers and internal teams to understand and act on. 

Bias for Action: Moves quickly, pushes deals forward, and takes initiative without waiting for direction. 

Required Skills 

• Deep industry knowledge enabling credible conversations about carrier workflows — you earn trust in the first meeting. 

• Genuine curiosity — ability to follow threads deeply, ask uncomfortable questions, and keep digging until the real pain surfaces. 

• Strong relationship-building ability with comfort working across executives, operators, and varied communication styles. 

• A repeatable objection-handling system that takes any pushback and converts it toward yes. • Ability to strategically navigate and tailor messaging to multiple stakeholders across complex deals. • Strong deal management and process discipline — deals move because you keep them moving. • Full ownership of pipeline outcomes — no excuses, just adjustments. 

• Clear, concise communication of ideas, value, and next steps for both internal and external audiences. 

Experience Level 

• 4–7+ years of B2B sales experience. 

• Experience at a large enterprise software company (Salesforce, Cisco, Oracle, or similar) followed by startup experience strongly preferred. 

• Demonstrated success closing complex enterprise deals. 

Even Better... 

• You've built or contributed to a channel or partnership motion that created net-new pipeline. 

• You bring market feedback to leadership in a structured, consistent way — patterns that influence product and roadmap, not just anecdotes. 

• You've used AI tools to meaningfully change how you sell — as a core part of your workflow, not just a productivity layer. 

What You'll Bring 

• Relentless curiosity about how businesses operate and where they break. 

• The ability to build trust quickly with industry operators and leadership — and maintain it through genuine relationship-building over time. 

• Comfort leading in-person meetings, executive conversations, and client entertainment.

• Strategic thinking around deal structure, business value, and long-term implications. • A proactive mindset and the ability to move deals forward without constant direction. • A collaborative approach to working with product, leadership, and customer teams. 

Our Values 

Ownership: You run your deals like a business. When something goes wrong, you don't look for reasons — you look for fixes. We take full accountability for outcomes, learn from what didn't work, and hold ourselves to a higher standard than anyone else would. 

Curiosity: We ask why until we actually understand. The best solutions come from the deepest questions. We follow threads, challenge assumptions, and never accept surface-level answers — in sales conversations, in product feedback, and in how we work. 

Intensity: We know we don't have the luxury of patience. We move fast, care deeply, and play to win. When something isn't working, we say so and fix it. When we lose, we talk about it honestly so we win next time. 

What We Offer 

• The opportunity to help define and scale sales at a fast-growing AI company. 

• Direct exposure to leadership and meaningful influence over product direction and roadmap. 

• Competitive base salary, uncapped commission, and equity in a company building category-defining technology. 

• A seat at the table — this is a founding-team-level sales role with long-term career upside.