Enterprise Account Executive

We’re partnered with Guava (https://goguava.ai/), an early-stage voice AI company building reliable technology for complex and highly regulated environments, to hire an Enterprise Account Executive.
This person will lead new-logo acquisition across Guava’s largest and most strategic accounts, building pipeline from the ground up and managing complex sales cycles across technical, operational, and executive stakeholders.
This person will lead new-logo acquisition across their largest and most strategic accounts, building pipeline from the ground up and managing complex sales cycles across technical, operational, and executive stakeholders.

What You’ll Do

• Own outbound prospecting and pipeline generation across strategic Enterprise accounts.
• Build account plans and map key stakeholders across Guava’s target industries.
• Run full-cycle Enterprise deals from first conversation through signed agreement, managing complex, multi-threaded sales processes.
• Lead discovery, solution positioning, and value-based selling with both technical and executive stakeholders.
• Partner with Solutions Engineering and Forward Deployed Engineering on technical evaluations, demos, and POCs.
• Navigate procurement, legal, security, and compliance requirements common within larger regulated organizations.
• Maintain disciplined pipeline management, forecasting, and CRM accuracy.
• Develop strong knowledge of Guava’s markets and the voice AI landscape, sharing customer and competitive insights with leadership.
• Represent Guava at industry events, conferences, and executive meetings.

What We’re Looking For

• 10+ years of Enterprise B2B sales experience with a consistent record of closing net-new logos.
• Experience selling complex technical or infrastructure products, including SaaS, APIs, AI/ML, voice, or communications technology.
• Proven success managing longer, multi-stakeholder Enterprise sales cycles, typically 3+ months.
• Experience selling within regulated or complex industries such as healthcare, financial services, or insurance.
• Comfortable selling to both technical buyers and senior business executives within the same deal.
• Strong outbound mentality with excellent executive presence and C-suite communication skills.
• Highly organized with disciplined pipeline management, forecasting, and CRM hygiene.
• Must be based in the United States.

Nice to Have

• Direct experience selling into healthcare systems, banking or lending, insurance carriers, or BPOs.
• Familiarity with compliance-driven buying environments involving SOC 2, HITRUST, PCI, or HIPAA.
• Early-stage or growth-stage startup experience helping define an Enterprise sales motion.
• Experience working alongside Solutions Engineering, Forward Deployed Engineering, or technical presales teams.

Why Guava

• Sell proven voice AI technology backed by more than a decade of experience in regulated production environments.
• Join early and play a meaningful role in shaping Guava’s Enterprise sales motion.
• Work closely with a highly technical team that can support complex customer evaluations and conversations.
• Have direct access to leadership and meaningful influence over how the GTM organization grows.
• Build strategic accounts in a voice AI market that is still early in its adoption curve.
• Competitive compensation with uncapped commission and equity.
• OTE: $300,000-$500,000, based on experience and success in the role.