The OpportunitySauce's Customer Success and Onboarding engines are already running with established processes and strong customer satisfaction. Now we're looking for a Head of Customer Success & Onboarding to strengthen, scale, and streamline these functions.
This is a
true player-coach role. You'll own strategic accounts and complex onboardings yourself, while elevating how the team operates-tightening predictability, sharpening communication, and making the customer journey more efficient and more consistent. You'll help the team execute with clarity and confidence, ensure customers feel supported at every step, and build systems that reduce friction for everyone.
Success in this role means smoother go-lives, better adoption, clearer expectations, and customers who stay and grow because Sauce has become essential to their business.
What You'll OwnTeam & Customer Outcomes
- Own team-level NRR/GRR, activation, time-to-value, and product adoption.
- Lead both CSM and Onboarding teams across customer segments-from long-tail to VIP.
- Ensure every customer follows a clearly defined, well-supported journey from contract to "Sauce is indispensable."
- Create a culture where follow-through, collaboration, and steady execution build trust-internally and with customers.
Build + Do (Player-Coach)
- Maintain, refine, and document onboarding and success playbooks so expectations are clear and consistent.
- Personally manage a small portfolio of strategic, complex, or at-risk accounts to stay close to customer needs and team realities.
- Work closely with Support to resolve issues quickly, spot patterns, and help translate learnings into product or process improvements.
- Model persistence, positivity, and outcome-oriented problem-solving for the team.
AI & Automation (Hands-On)
- Build AI-powered automations across the entire org-not just CS and Onboarding Identify manual work everywhere it lives, then ship the automations that eliminate it.
- Lead by example: prototype, deploy, and iterate yourself rather than handing it off.
Process & Tooling
- Maintain clean health scores, workflow tracking, and task management across the CS platform/CRM.
- Define and track SLAs for onboarding, activation milestones, and ongoing engagement.
- Partner with RevOps/Ops to maintain dashboards that give the team clarity and help guide day-to-day priorities.
- Use data to identify bottlenecks and opportunities - testing improvements and iterating thoughtfully.
Cross-Functional Collaboration
- Align with Sales on clean, predictable handoffs and standardized customer expectations.
- Partner with Product to surface customer insights, support betas, and ensure feedback drives continuous improvement.
- Work with Marketing to generate testimonials, case studies, and referrals from successful customers.
- Foster open, positive communication across functions so teams move in sync.
What Success Looks Like- First 90 Days - Organize & Uplevel
- Develop a clear understanding of current CS and Onboarding workflows, identifying friction points and opportunities.
- Tighten handoffs, communication rhythms, and milestone tracking across the customer journey.
- Implement a handful of practical, impactful improvements-such as more structured kickoff flows, simplified checklists, or improved internal visibility.
- First Year - Consistent, Scalable Customer Journeys
- Deliver more predictable onboarding timelines and smoother go-lives for all customer segments.
- Improve logo retention and NRR across the team's managed book of business.
- Reduce reliance on tribal knowledge by codifying processes, expectations, and best practices.
- Build a high-performing, trusted team with clear goals, strong coaching rhythms, and healthy cross-functional relationships.
What You Bring- Must-Have
- 6-8+ years in Customer Success and/or Onboarding within B2B SaaS, with 2-4 years leading teams.
- A proven ability to improve retention, adoption, onboarding speed, or customer health.
- Comfort operating at the detailed level-workflows, tickets, handoffs, timelines, and process mapping.
- Excellent communication skills, with empathy for busy, often non-technical SMB customers.
- A leadership style rooted in clarity, consistency, persistence, and positive problem-solving.
- Ideal
- Experience working with restaurants or other local SMBs.
- Experience overseeing both onboarding and post-go-live success under one team.
- Familiarity with CS tools, playbooks, automation, and lightweight operational systems.
What We Offer:- Strong & Competitive Compensation Package, Including Equity
- Company-Sponsored Insurance Package (Health, Dental, Vision, Mental Health)
- Paid Parental Leave
- Flexible Work Environment
- Responsible Paid Time Off Policy
