Head of Sales

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

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