[Hiring] Mid-Market Account Executive @StartupTAP

Role Description

This person will drive new-logo growth across Guava’s mid-market segment, owning the full sales cycle from prospecting through close while building a strong, consistent pipeline across the company’s core verticals. This is a high-autonomy hunting role for someone who thrives in a faster sales motion and is comfortable selling a technical product to both technical and business stakeholders, often within the same sales cycle.

• Own outbound prospecting and pipeline generation across mid-market accounts, building your own book of business.
• Identify and engage key decision-makers across technical, operational, and executive functions.
• Develop opportunities across Guava’s core verticals, including healthcare, banking, insurance, BPOs, and tech-native companies.
• Partner with marketing and SDR resources to convert inbound interest into qualified mid-market opportunities.
• Run full-cycle sales processes from initial outreach and discovery through negotiation and signed contract.
• Lead discovery, solution positioning, and value-based conversations with technical buyers such as Engineering Leaders and CTOs, as well as business buyers including VPs of Operations, COOs, and CROs.
• Partner closely with Solutions Engineering and Forward Deployed Engineering teams throughout technical evaluations and demos.
• Handle objections, negotiate terms, and drive opportunities to close with urgency.
• Maintain disciplined pipeline management, forecasting, and CRM hygiene.
• Develop strong knowledge of Guava’s target industries and the broader voice AI landscape, bringing prospect and market feedback directly to leadership.

Qualifications

• 5+ years of B2B SaaS or technology sales experience with a consistent record of meeting or exceeding quota on net-new business.
• Proven full-cycle sales experience, including independently generating pipeline and taking opportunities from prospecting through close.
• Strong outbound orientation and comfort building business rather than relying primarily on inbound opportunities.
• Experience selling to both technical and business stakeholders, sometimes within the same sales process.
• Familiarity with mid-market sales motions involving faster cycles, fewer stakeholders, and strong value-based selling.
• Strong written and verbal communication skills with the ability to lead effective discovery, demos, and follow-up.
• Highly organized, coachable, and energized by performing in a fast-moving environment.
• Must be based in the US. This is a full-time, remote position.

Requirements

• Experience selling AI, voice, communications technology, or other technical products.
• Experience selling into healthcare, financial services, insurance, BPOs, or technology companies.
• Familiarity with compliance-driven buying environments involving SOC 2, HITRUST, PCI, or HIPAA.
• Early or growth-stage startup experience helping define or build a sales motion.
• Experience partnering closely with Solutions Engineering, Forward Deployed Engineering, or technical presales teams.

Benefits

• Join an early-stage AI company tackling voice technology in environments where reliability, security, and compliance are critical.
• Sell a platform backed by years of experience operating voice technology in regulated production environments.
• Enter at a stage where the mid-market sales motion is still being shaped, giving you meaningful influence over how the company goes to market.
• Work closely with a highly technical team that can support technical evaluations, demos, and complex customer conversations.
• Maintain a direct line to company leadership and contribute market feedback that can influence product and GTM strategy.
• Join a high-ownership environment with opportunities to grow alongside the organization.
• Competitive base salary, uncapped commission, and equity.
• OTE range: $230,000-$270,000, based on experience and performance.