Digital Customer Success Lead

We're hiring a Digital Customer Success Lead. This is a builder role. You will design and operate the digital-first success motion for our SMB segment. This includes automated lifecycle journeys, scalable adoption programs, and AI-powered interventions. This is a hands-on role at a company that moves fast - expect to build, measure, iterate, and own outcomes.

• Design and own the full digital customer journey for the SMB segment, from onboarding through renewal - automated touchpoints, milestone triggers, adoption nudges, and health-based interventions.
• Build and manage lifecycle email and in-app campaigns that drive product adoption and surface value at the right moments, using behavioral and health score signals.
• Identify the leading indicators of retention in this segment and create proactive playbooks that engage our customers.
• Leverage AI tools to automate outreach, personalize communication at scale, and improve the efficiency of the digital CS motion.
• Instrument everything — define the metrics, track what's working, and report clearly on program performance and segment health.
• Work cross-functionally with Product, Marketing, and Implementation to align messaging, timing, and channel strategy for SMB customers.
• Build and run scalable webinar programs that educate customers and deepen product adoption across our customer base.

• 3–6 years in customer success, with time spent building or running a scaled digital or tech-touch CS program with measurable outcomes.
• Demonstrated experience designing automated customer lifecycle journeys - you've built one before and can build one again.
• Comfort working with customer health data, usage signals, and segmentation to drive program design decisions.
• Strong written communication skills — you write crisp, effective copy for customer-facing journeys and internal documentation.
• AI-first mindset — you've used AI tooling in your CS workflows (automated outreach, smart triggers, analysis, or similar), have proven outcomes, and you stay current on what's emerging.
• Operational rigor — you set up measurement before you launch programs, not after.
• Collaborative, low-ego, and comfortable building in ambiguous environments.
• Bias for action — you move from insight to hypothesis to test quickly, synthesize what you learn, and iterate without waiting for perfect conditions.
• Strong cross-functional instincts — you understand how to stay aligned with Marketing, Product, and other partners, keep projects moving, and give and receive feedback effectively at every level.

Bonus Points if you have:

• Experience in B2B SaaS serving SMB customers.
• Experience managing offshore team members.
• Background in accounting, professional services software, or fintech.

• Gain global experience across the USA, Australia, New Zealand, UK, Canada and the Philippines
• Excellent benefits package including:
  • Paid Flexible Time Off with an encouraged 3 weeks use per year
  • Company paid medical for you and eligible spouse/partner and dependents
  • Company paid dental and vision and eligible spouse/partner and dependents
  • Fully company funded short and long term disability
  • Fully company paid life insurance
  • 401(k) with company matching
  • Flexible Spending Account
  • Up to 8 weeks paid parental leave
  • Work-from-home stipend
• Work with (and learn from) an experienced, high-performing team
• A collaborative, team-oriented culture that embraces diversity, invests in development and provides consistent feedback
• Be part of a fast-growing company that firmly believes in promoting high performers from within