Founding Customer Success bei Pear VC

Location: New York City (5 days in-office)
Experience: 2-5 years
Type: Full-time

The Opportunity

We're building the AI operating system for America's 33 million small businesses—and we're moving fast. We grew 10x last year, we're up 20% month-over-month, and we recently raised a $3M seed from Pear VC. With 500+ businesses already using Frontdesk and seven-figure ARR, we've proven the model works. Now we need the right customer success leader to help us scale it.

Our Vision: The SMB Super App

We started with AI receptionists that answer calls and book appointments. But we quickly realized we were building something far bigger: the first AI-native operating system for small businesses.

Every phone call, text, and booking creates a living customer record. Our AI agents learn from conversations. Then, that intelligence powers outbound campaigns that re-engage customers at exactly the right moment, driving real revenue growth. We're not a point solution. We're the complete Customer Revenue Engine.

SMBs represent half of US GDP, yet they've been ignored by companies like Salesforce and underserved by tools built for enterprise sales teams. While everyone else chases enterprise deals, we've discovered an explosive path to market where no one else is looking. Our early traction proves it: SMBs need AI solutions just as much as enterprises do—they just need them built differently.

We're here to build the super app that finally gives them what they deserve.

About the Role

We're hiring our first US-based Customer Success Manager to own our highest-value customer relationships while building the foundation for our global CS organization. This is a rare ground-floor opportunity to define customer success at an AI company scaling from startup to category leader.

You'll directly manage ~100 mid-market/strategic accounts (our $15K-$25K+ clients) while helping guide our Philippines CSM team across all customer tiers. This role uniquely blends individual contributor ownership of $1M+ ARR with player-coach leadership of a global team. It combines hands-on technical work, strategic account management, and expansion revenue responsibility.

What You'll Do

Account Ownership & Growth

• Own the full lifecycle for 100+ high-value accounts from onboarding through renewal

• Drive expansion revenue by identifying and closing upsell opportunities into outbound calling, chatbots, and lead form products

• Unique opportunity to gain upside commission as part of sourced revenue

• Maintain 95%+ retention across your portfolio through proactive engagement

Technical Onboarding & Integration

• Configure enterprise-level AI setups across voice, chat, and form products

• Build and troubleshoot Zapier automations, CRM integrations (HubSpot, Salesforce), and calendar connections

• Set up and QA multi-channel customer environments to ensure flawless go-live experiences

• Reduce time-to-value for new clients from weeks to days

Proactive Performance Management

• Monitor call logs, chat transcripts, and usage data daily to catch issues before customers notice

• Analyze product performance metrics and usage patterns to identify expansion opportunities

• Generate actionable insights for product and engineering teams based on customer behavior

Global Team Leadership

• Conduct weekly audits and coaching sessions with the Philippines CSM team (8 people managing 600+ accounts)

• Ensure HubSpot data integrity and process consistency across all customer touchpoints

• Build scalable playbooks for onboarding, troubleshooting, and team training

• Drive team performance improvements toward 2x conversion rates and 95%+ CRM accuracy

Strategic Impact

• Report directly to the CEO with immediate visibility into company strategy

• Influence product roadmap through synthesized customer feedback

• Document and refine processes that enable hiring of additional US CSMs

• Help structure the global CS organization into specialized roles with clear KPIs

Product Insights

• Collaborate with product and engineering to implement insights from onboardings and success calls

• Collect data across the CSM team that can funnel back to product and engineering

What We're Looking For

Must-Haves

• 2-5 years of experience in customer success, account management, or customer-facing technical roles

• Zapier & integration platforms – Hands-on experience building automations and connecting systems (CRMs, calendars, third-party apps)

• Advanced CRM proficiency – Power user of HubSpot or Salesforce who can build reports, audit data, and manage complex customer records

• API/connector understanding – Comfortable troubleshooting data flows and webhook integrations without engineering support

• Multi-channel product setup – Ability to configure and QA complex technical products across customer environments

• Technical troubleshooting skills – Can diagnose integration issues, document clearly for engineering, or fix independently

• Revenue mindset – Comfortable with expansion quotas and identifying upsell opportunities. There is a unique opportunity to gain upside commission as part of sourced revenue

• Player-coach mentality – Can lead without formal authority while maintaining individual account excellence

Nice to Haves

• Data analysis skills (Excel/Sheets power user) for analyzing usage patterns and health metrics

• Conversion rate optimization (CRO) experience—understanding funnel performance and lead capture optimization

• Light scripting abilities (JavaScript, Python, or SQL) for custom reporting/automation

• Experience at high-growth B2B SaaS companies (bonus: Zapier, DoorDash, or similar)

Growth Trajectory

3 months: Own all mid-market/strategic accounts accounts, establish team audit cadence, prevent pilot failures, drive initial expansion deals

6 months: Achieve 95%+ retention, generate $100K+ expansion revenue, reduce onboarding time dramatically

12 months: Command $2M+ ARR with 120%+ net revenue retention, Philippines team fully self-sufficient, ready to scale US team

Year 2+: Potential evolution to Head of Customer Success or VP Customer Success, hiring and managing 2-3 US CSMs, owning enterprise specialist role with $50K-$100K+ accounts

Why This Role Is Unique

• Hybrid CSM + Account Manager – Own both retention and expansion with a unique opportunity to gain upside commission as part of sourced revenue

• IC with team leadership impact – Influence 600+ accounts without formal reports

• Unusually technical – Hands-on integrations and automation vs. relationship-only roles

• Ground-floor opportunity – Build the playbook and team structure from scratch

• Executive visibility – Direct CEO reporting with immediate strategic impact

• AI product complexity – Work at the cutting edge of conversational AI technology

Location

New York City office, 5 days per week in-person

AI Frontdesk is building the future of customer communication through voice AI, chatbots, and intelligent lead capture. Join us at the ground floor of transforming how businesses connect with their customers.