Senior Mid-Market Account Executive

Startuptap | Voice AI technology

1h 50m ago

Remote In-Country

Full Time

United States of America

$230k - $270k USD/yr

We’re partnered with Guava ( ), an early-stage voice AI company building reliable technology for complex and highly regulated environments, to hire a Mid-Market Account Executive.

This person will drive new-logo growth across the Mid-Market segment, owning the full sales cycle from prospecting through close. You’ll work across Guava’s core verticals, including healthcare, financial services, insurance, BPOs, and technology, selling to both technical and business stakeholders.

This is a high-autonomy hunting role for someone who enjoys building pipeline, moving quickly, and joining a sales organization while there is still meaningful opportunity to help shape how the team goes to market.

What You’ll Do

Own outbound prospecting and pipeline generation across Mid-Market accounts.
Identify and engage key decision-makers across both technical and business functions.
Partner with Marketing and SDRs to turn inbound interest into qualified opportunities.
Run full-cycle deals from initial outreach through close, managing shorter and mid-length sales cycles with speed and discipline.
Lead discovery and solution positioning with technical buyers, including engineering leaders and CTOs, as well as business and operations stakeholders.
Work closely with Solutions Engineering and Forward Deployed Engineering on demos and technical validation.
Handle objections, negotiate terms, and keep opportunities moving toward close.
Maintain accurate pipeline, forecasting, and CRM activity.
Bring prospect and market feedback back to leadership as Guava continues refining its Mid-Market motion.

What We’re Looking For

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 from prospecting through close, with a strong outbound mentality.
Comfortable selling to both technical and business stakeholders within the same sales process.
Experience with Mid-Market sales motions, including faster cycles and strong value-based selling.
Strong written and verbal communication skills, including effective demos and follow-up.
Organized, coachable, and comfortable operating in a fast-moving environment.
Must be based in the United States.

Nice to Have

Experience selling AI, voice, communications technology, or other technical products.
Experience within healthcare, financial services, insurance, BPO, or technology.
Exposure to compliance-driven buying environments involving SOC 2, HITRUST, PCI, or HIPAA.
Startup or high-growth experience helping build or refine a sales playbook.
Experience partnering with Solutions 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 help shape Guava’s Mid-Market sales motion as the team continues to scale.
Work alongside a strong technical team that supports customer conversations, demos, and technical evaluations.
Have direct access to leadership and an opportunity to influence how the sales organization develops.
Grow with an early-stage company where strong performers can take on increasing responsibility over time.
Competitive compensation with uncapped commission and equity.
OTE: $230,000-$270,000, based on experience and success in the role.

Required Languages

🇬🇧 English

What You’ll Do

Own outbound prospecting and pipeline generation across Mid-Market accounts.

Identify and engage key decision-makers across both technical and business functions.

Partner with Marketing and SDRs to turn inbound interest into qualified opportunities.

Run full-cycle deals from initial outreach through close, managing shorter and mid-length sales cycles with speed and discipline.

Lead discovery and solution positioning with technical buyers, including engineering leaders and CTOs, as well as business and operations stakeholders.

Work closely with Solutions Engineering and Forward Deployed Engineering on demos and technical validation.

Handle objections, negotiate terms, and keep opportunities moving toward close.

Maintain accurate pipeline, forecasting, and CRM activity.

Bring prospect and market feedback back to leadership as Guava continues refining its Mid-Market motion.

What We’re Looking For

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 from prospecting through close, with a strong outbound mentality.

Comfortable selling to both technical and business stakeholders within the same sales process.

Experience with Mid-Market sales motions, including faster cycles and strong value-based selling.

Strong written and verbal communication skills, including effective demos and follow-up.

Organized, coachable, and comfortable operating in a fast-moving environment.

Must be based in the United States.

Nice to Have

Experience selling AI, voice, communications technology, or other technical products.

Experience within healthcare, financial services, insurance, BPO, or technology.

Exposure to compliance-driven buying environments involving SOC 2, HITRUST, PCI, or HIPAA.

Startup or high-growth experience helping build or refine a sales playbook.

Experience partnering with Solutions 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 help shape Guava’s Mid-Market sales motion as the team continues to scale.

Work alongside a strong technical team that supports customer conversations, demos, and technical evaluations.

Have direct access to leadership and an opportunity to influence how the sales organization develops.

Grow with an early-stage company where strong performers can take on increasing responsibility over time.

Competitive compensation with uncapped commission and equity.

OTE: $230,000-$270,000, based on experience and success in the role.