Founding Customer Success - AI Frontdesk

Company: Pear VC
Location: New York City
Posted on: April 1, 2026

Job Description:

Founding Customer Success Manager AI Frontdesk | New York City (5 days in-office) | Full-time | 2-5 years experience About Us We're building the AI operating system for America's 33 million small businesses. What started as AI receptionists has evolved into the first complete Customer Revenue Engine for SMBs—turning every phone call, text, and booking into actionable intelligence that drives real revenue growth. We grew 10x last year, we're up 20% month-over-month, and just raised $3M from Pear VC. With 500 businesses using Frontdesk and seven-figure ARR, we've proven the model works. While everyone else chases enterprise deals, we've discovered an explosive path to market where no one else is looking: SMBs need AI just as much as enterprises do—they just need it built differently. The Role You'll be our first US-based Customer Success Manager, owning 100 high-value accounts ($1M book of business) while building the foundation for our global CS organization. This is a rare player-coach role that combines hands-on technical ownership with team leadership—you'll manage strategic accounts directly while guiding our Philippines CSM team across 500 customers. You'll report directly to the CEO with immediate influence on product roadmap, company strategy, and the future structure of our CS org. What You'll Do Retain & Expand for 100 mid-market/strategic accounts ($15K-$25K ACV), driving 95% retention and identifying expansion opportunities across voice, chat, and lead capture products. You'll have a unique opportunity to gain upside commission as part of sourced revenue Configure complex, no-code technical setups including Zapier automations, CRM integrations (HubSpot, Salesforce), and multi-channel AI environments—reducing time-to-value from weeks to days Monitor and optimize call logs, chat transcripts, and usage metrics daily to catch issues before customers notice and uncover expansion plays Lead global team performance through weekly coaching sessions with Philippines CSMs, building scalable playbooks and driving toward 2x conversion rates and 95% CRM accuracy Shape product direction by synthesizing customer insights and reporting directly to leadership on strategic opportunities Build the CS playbook from the ground up—document processes, establish KPIs, and create the foundation for scaling to a team of US CSMs Who You Are Technically fluent with 2-5 years in customer success or account management—you're a HubSpot/Salesforce power user who builds Zapier automations and troubleshoots API integrations without engineering support Revenue-driven with a track record of hitting expansion quotas and identifying upsell opportunities (expansion commission available) Player-coach who can lead without formal authority while maintaining excellence across your own book of business Proactive problem-solver who catches issues early, documents clearly, and knows when to escalate vs. fix independently Process builder excited to create scalable systems and train teams, not just manage accounts Nice to Have Data analysis chops (Excel/Sheets wizardry) for usage pattern analysis and health scoring Conversion rate optimization to guide customers on how our tool can get them more customers Light scripting ability (JavaScript, Python, SQL) for custom automation High-growth B2B SaaS experience (bonus points for Zapier, DoorDash, or similar) Why Join Us Ground-floor impact : Define customer success at an AI company scaling from startup to category leader—build the playbook, team structure, and culture from day one Rapid career growth : Clear path to Head of CS or VP Customer Success within 18-24 months, managing a team of US CSMs and owning enterprise accounts ($50K-$100K ACV) Executive visibility : Direct CEO reporting with real influence on product roadmap and company strategy Cutting-edge product : Work at the forefront of conversational AI and watch your customers transform their businesses in real-time Hybrid ownership model : Unique blend of retention excellence and expansion revenue—own both the relationship and the growth What We Offer Compensation : Competitive base salary expansion commission on sourced revenue Equity : Meaningful early-stage equity package Location : New York City office, 5 days per week in-person Growth : Accelerated path to leadership with clear milestones and CEO mentorship AI Frontdesk is transforming how small businesses connect with their customers. Join us at the ground floor.

Keywords: Pear VC, Waterbury , Founding Customer Success - AI Frontdesk, IT / Software / Systems , New York City, Connecticut