Head of Sales

Ascend is transforming the $10 trillion global insurance industry by combining AI automation with embedded fintech.

While insurance represents 7.2% of global GDP, outdated financial infrastructure like PDFs, emails, and manual reconciliation continues to slow the industry down. Ascend is the first and market‑leading finance automation platform built specifically for insurance, driving the industry’s rapid digital transformation.

In just three years :

Trusted by thousands of insurance businesses nationwide

Processes billions in transactions annually, growing 200%+ per year

Built a world‑class team of 50+ across San Francisco and Columbus

How We Do It

Ascend automates the entire insurance financial lifecycle—from collections and accounting to reconciliations and disbursements—helping businesses streamline operations and increase profitability.

In the AI era, software alone is no longer enough. For decades, software costs have declined, and with AI, they’re now in free fall. As both software buyers and builders, we fully embrace this shift—it makes technology more powerful and accessible. However, businesses must also maximize monetization, and the future belongs to those that embed themselves into financial flows rather than simply selling SaaS.

That’s why AI + fintech is our edge—seamlessly integrating financial automation into transactions to create real, lasting value. Customers don’t just buy software; they unlock powerful financial efficiencies with a 5–7x ROI.

Why We Do It

Insurance is a $10 trillion-plus industry running on legacy systems. AI alone won’t fix it, but AI‑powered automation embedded into payments and transactions will.

Ascend’s mission is to become the leading financial automation platform for insurance by 2030—powering the entire industry’s financial operations while transforming the way trillions of dollars move.

Your Role

As the Head of Sales at Ascend, you will lead our Sales team—responsible for winning new logos across SMB, Mid‑Market and Enterprise segments and expanding existing customer relationships. You’ll help us take our Sales organization to the next level by leading our growing team of AEs, designing scalable systems, managing forecasting with precision, and personally owning key strategic accounts to demonstrate sales mastery to the team. This is a player‑coach role that combines leadership, operational rigor, and executive‑level selling.

We are hiring for this position in either San Francisco, CA or Columbus, OH.

Responsibilities

• Build and lead a high‑bar team culture with clear expectations, performance reviews, and quota accountability.
• Hire, onboard, and coach top‑performing AEs, driving sales discipline and consistent quota attainment.
• Own full‑cycle sales playbooks for different segments (SMB / Medium vs. Enterprise / Strategics).
• Lead forecasting and pipeline management with clean data hygiene, accurate commits, and stage discipline.
• Design and manage the coverage model —capacity, quotas, account assignment, and resourcing plans.
• Personally own and drive strategic accounts , modeling enterprise selling and CxO engagement.
• Codify repeatable patterns from strategic deals into scalable enablement assets (ROI tools, templates, FAQs).
• Partner with RevOps, Finance, and CS on deal economics, enablement, and expansion initiatives.
• Collaborate with Marketing to refine message architecture and competitive positioning.

Qualifications

Benefits

We are committed to equal opportunity employment and embrace diversity within our organization. We do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

We encourage candidates to apply even if their experience doesn't precisely match this opportunity. We value diversity and are dedicated to equal opportunity employment.

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