Head of Sales

Insurance is a $10T industry still running on PDFs, email threads, and manual reconciliation. Ascend is changing that.

We built the first finance automation platform designed specifically for insurance — combining AI and embedded fintech to modernize how money moves across the entire policy lifecycle, from collections to disbursements. In five years, we've become the market leader: trusted by thousands of insurance businesses nationwide, processing billions in transactions annually, and growing 200%+ year over year.

How We Do It

Ascend automates the financial operations that insurers, MGAs, and agencies run every day — and embeds directly into the transactions where money actually moves.

AI is driving the cost of software toward zero. The companies that win won't just sell tools — they'll capture value at the point of the transaction itself. Ascend is built for exactly that moment. Our customers don't just adopt software; they unlock measurable efficiency with a proven 5–7x return on investment.

Our 70+ person team, based in San Francisco and Columbus, brings together deep expertise in insurance, fintech, and AI to build infrastructure the industry has never had.

Why We Do It

The insurance industry intermediates trillions of dollars — and almost none of that infrastructure was built for the modern era. Legacy systems aren't just inefficient; they're a ceiling on what the industry can become.

Ascend's mission is to become the leading financial automation platform for insurance by 2030 — powering the financial operations of the entire industry and transforming the way trillions of dollars move. We're not building another point solution. We're building the financial backbone of insurance.

Your Role

Ascend is looking for a Head of Sales to lead our sales organization and own our closed won deals goals. You'll inherit a strong foundation — defined segments, active pipeline, and a GTM motion that's working — and your job is to take it to the next level. You'll lead a team of 8-10 AEs across SMB, Mid-Market, and Enterprise, drive forecast discipline, and be a player-coach in our most important deals.

We are hiring for this position in San Francisco, CA.

Responsibilities will include

Objective #1: In your first 30 days, develop an understanding of how each of our AEs sells Ascend’s products in their respective segments

• Develop a deep understanding of Ascend's product lines and how each maps to SMB, Mid-Market, and Enterprise buyer personas
• Shadow AE calls, deal reviews, and customer conversations to calibrate where the team is excelling and where there are areas of improvement
• Audit the current sales org: pipeline health, quota attainment by rep, forecast accuracy, and gaps in the existing playbook across segments
• Align with the CEO and RevOps on near‑term targets, priorities, and key decisions for the first 90 days
• Build relationships cross‑functionally with Marketing, Customer Success, Product, and Finance to understand how Sales connects to the broader GTM machine

Objective #2: In your first 60 days, take ownership of the pipeline, weekly meetings, and coaching AEs

• Own closed won results end‑to‑end — manage forecasting, establish stage discipline, commit cadences, and data hygiene standards that give leadership accurate visibility into the business.
• Identify performance gaps and begin focused coaching tailored to each AE
• Engage directly in key deals as a player‑coach — leading or supporting Enterprise/Strategic pursuits where executive presence and deal strategy matter
• Take over running our weekly sales calls: weekly meetings, pipeline review with revenue operations, and team call reviews to foster shared learnings and feedback across the team

Objective #3: In your first 90 days, fully own KPIs and enhance collaboration with marketing and customer success

• Full settled into steady‑state expectations of the role — owning and hitting metrics, coaching, managing, and leading the team, supporting deals with a strong understanding of our products and customers.
• Refine and own KPIs and reporting rhythms that give the team and leadership a shared view of pipeline health, rep performance, and segment economics
• Partner with Marketing on lead generation, message architecture, and competitive positioning — ensuring Sales and Marketing are running a coordinated GTM motion
• Collaborate with Customer Success on expansion and cross‑sell strategy; ensure Sales‑to‑CS handoffs are airtight and that land‑and‑expand is a first‑class motion
• Begin hiring or backfilling any gaps — raising the talent bar while maintaining team momentum

You might be a good fit if you are / have

• 8+ years in B2B technology sales, with experience across multiple segments — you've sold SMB and you've run enterprise deals
• 2+ years leading quota‑carrying sales teams with a track record of building high‑performance culture and consistent attainment
• Strong exposure or experience with other parts of revenue org (CS, marketing, rev ops, etc)
• Strong forecasting discipline — you've run a clean forecast, and you know how to coach reps to do the same
• Experience with land‑and‑expand motions; ideally with strong NDR as a north star
• Comfortable in the player‑coach seat — you can run a deal and develop a rep in the same week
• Excellent communication and executive presence; you can hold a room with a CFO and also run a tight deal review
• Insurance, financial services, or payments experience is a plus
• High‑growth startup experience preferred — you've built something before, not just managed something that was already built

OTE $350,000-400,000

All roles at Ascend are 5 days a week onsite at our beautiful office in SoMa!

• 100% health premiums covered for you and your dependents
• 401k with employer matching options
• A fast growing team with an emphasis on promoting from within 80% of all hires in the last 12 months have already been promoted!
• Unlimited PTO
• Company paid commuter benefits
• Parental and family leave
• Dog‑friendly office!

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.