Founding Head of Sales - $400k OTE - NYC Hybrid - FSI Market Focus SaaS

Early Stage Sales Builders in NYC, Are You Ready to Scale a $4M SaaS Business to $20M+?

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If you've taken a SaaS product from $4M-$20M+ ARR, sold into the FSI market, and want to build something real with full autonomy, this one’s for you. This is your chance to own revenue, build your team, and lead the next phase of growth from the ground up, with elite major clients already on the books and expanding.

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The unique thing about this business is the strong traction they've had with a team of just 2 AEs and 1 AM. Many $4M ARR businesses need 8 reps to reach this number. The tool is strong, has a strong advantage in the quality of data it uses and the backing of the larger company with a strong 25 year history, VS a some kind of high risk startup with a first time founder.

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Exec Summary:

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• Role: Founding Head of Sales  
• Industry: Conversational Intelligence SaaS with an FSI ICP focus.  
• Location: NYC Hybrid (ideally within 30 minutes of Manhattan)  
• Base Salary: $200K-$240K  
• OTE: $350K-$400K + Equity  
• Stage: ~$4M ARR → targeting $20M+ over 24-36 months  
• Team: Lead 3 AEs today, scale to 6–10 within Year 1  
• Client logos: Goldman Sachs, Morgan Stanley, Skadden, Wilson Sonsini and Adobe  
• Focus: Own GTM, build the team, scale strategic sales into FSI, Legal & Professional Services

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Why This Role and Why Now?

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• The product solves a top-of-funnel pain for enterprise sellers: how to open doors through warm executive access, not relying on volume based outdated cold outbound and automation  
• It’s already winning in financial services and legal, sectors notoriously hard to break into  
• The business is growing quickly without brand awareness or inbound, now ready to scale with the right leader  
• You’ll take a proven revenue base (~$4M ARR), and build the GTM structure on strong foundations to achieve the $100M+ ARR goal the CEO is working towards here.  
• The CEO is hands-on, ambitious, and wants a true player-coach to build a great team and GTM engine with.

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What You Will Be Doing?

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• Own the GTM motion, from quota to hiring, pipeline to pricing  
• Personally run point on 8-10 strategic accounts while you learn how best to systemise what works  
• Sell into Finance, Legal, RevOps, GTM, Compliance - enterprise and mid-market  
• Define ICP, vertical strategy, comp plans, and outreach process  
• Embed structure: deal reviews, forecasting, coaching, hiring  
• Work directly with the CEO to define and evolve the commercial model

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Success in the Role

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First 3 Months

• 2 Additional AEs hired and ramping  
• Personally work deals to learn the motion, build the playbook and start to establish a repeatable sales motion  
• Pipeline strategy in place and showing early traction

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By Month 6

• Team performing against ramp target  
• Clear segmentation and account prioritisation strategy in place  
• Revenue plan tracking to goal

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End of Year 1

• On path to $8M+ ARR  
• Hiring pipeline to scale to 6-10 reps  
• Process, team and GTM engine ready for $20M+ trajectory, and beyond.

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What You Bring

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• Experience in FSI, legal, insurance or similarly complex markets  
• Deep investment banking knowledge (not just FS broadly)  
• Or strong SaaS + data/CRM platform sales experience  
• The gravitas to lead a senior team  
• A strategic mindset with a hands-on, builder mentality  
• Comfort operating outbound, multi-threaded sales in high-resistance sectors

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What Won't Work Now

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• You haven’t sold into regulated, relationship-led sectors like FSI, legal or professional services  
• You’ve never built a sales team or sales motion and scaled up the team and performance  
• You’re not NYC-based (or can’t be in person regularly with the CEO, team and clients)

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Role Summary

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• Role: Founding Head of Sales  
• Industry: Conversational Intelligence SaaS with an FSI ICP focus.  
• Location: NYC Hybrid (ideally within 30 minutes of Manhattan)  
• Base Salary: $200K-$240K  
• OTE: $350K-$400K + Equity

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This is a high-impact leadership opportunity for a proven sales leader who can both show the way, and build the systems and team around them.  

If you’re ready to take on a startup with good PMF and develop it into a true enterprise revenue growth engine who punches well above it's weightclass, apply now and let’s talk.