We are looking for a Manager of SMB Customer Success to lead and grow our small but mighty SMB CS team. This is a player-coach role for someone who has built or scaled a digital-first, tech-touch customer success motion - and who knows how to drive retention and adoption at volume without sacrificing the customer experience. You'll inherit a team of 2-3 CSMs and be responsible for building the systems, playbooks, and automation infrastructure that allow a small team to manage a large book of business efficiently. This is not a high-touch, white-glove CS role - it's a scaled motion role, and the right person is energized by that challenge. What You'll Do Team Leadership • Manage, coach, and develop a team of 2-3 SMB Customer Success Managers • Build a performance culture grounded in clear metrics, regular feedback, and accountability • Hire and onboard future team members as the SMB segment grows Digital & Scaled Motion Design • Design and operationalize a digital-first CS motion that drives adoption, retention, and expansion across a high-volume SMB customer base • Build and optimize automated lifecycle programs - onboarding sequences, health-based triggers, renewal campaigns, and re-engagement workflows - using tools like Salesforce, HubSpot, or equivalent • Develop and maintain a library of digital touchpoints including in-app messaging, email nurture sequences, self-serve onboarding resources, and video content • Identify where human intervention adds the most value and design the motion accordingly, protecting CSM time for the highest-impact moments Retention & Expansion • Own GRR and NRR targets for the SMB segment • Monitor customer health signals and ensure the team is proactively addressing risk before it becomes churn • Partner with Account Managers to identify expansion and upsell opportunities within the SMB base • Establish and track leading indicators that predict renewal outcomes 60-90 days in advance Operations & Reporting • Build and maintain dashboards that give CS leadership real-time visibility into team performance, customer health, and segment-level risk • Define and track the KPIs the team is measured against, including adoption milestones, health scores, renewal rates, and response SLAs • Partner with CS Ops, Product, Support, and Marketing to continuously improve the digital customer experience What We're Looking For • 5+ years of experience in Customer Success, with at least 2 years in an SMB or scaled/digital motion environment • 1-2+ years of people management experience, including coaching and developing CSMs • Proven track record of building or optimizing a tech-touch or digital CS motion - not just operating within one • Deep familiarity with CS platforms (Vitally, ChurnZero, Totango, or equivalent) and how to use automation to drive outcomes at scale • Strong analytical mindset - comfortable in data, building dashboards, and making decisions based on leading indicators • Experience owning GRR/NRR metrics at the segment level • Ability to think like a marketer: customer segmentation, lifecycle design, message sequencing, and engagement optimization • Comfortable in a fast-paced, high-growth environment where the playbook is still being written • US-based; no travel required Bonus Points • Experience in legaltech, professional services, or a vertical SaaS environment • Familiarity with AI-powered products and helping non-technical users adopt new workflows • Background in customer marketing, lifecycle marketing, or growth Benefits & Perks: As part of our total rewards package, we offer attractive benefits and perks to our employees, including: • Choice of medical, dental, and vision insurance plans for you and your family. • Additional insurance coverage options for life, accident, or critical illness. • Flexible paid time off, sick leave, short-term and long-term disability. • 10 US observed holidays, and Canadian statutory holidays by province. • A home office stipend. • 401(k) for US-based employees and RRSP for Canada-based employees. • Paid parental leave. • A local in-person meet-up program. • Hubs in San Francisco and Toronto. Please note the above benefits & perks are for full-time employees