Founding Customer Success - AI Frontdesk

Pear VC•New York, NY

60d•Onsite

About The Position

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. 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.

Requirements

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 Haves

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)

Responsibilities

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