Sr. Customer Success Manager II, RMM

A Day in The Life

As a Senior Customer Success Manager II, you are the highest escalation tier and the ultimate strategic safeguard for our most complex mid-market accounts. You will manage a high-touch, high-value regional book of business comprising complex, multi-location restaurant brands.

While standard CSMs manage proactive adoption, you are the dedicated specialist for the department’s most critical interventions—stepping into situations where accounts are highly escalated, severely at risk, or facing deeply nuanced technical hurdles. You will partner directly with C-suite executives, founders, and Toast engineering leadership to salvage at-risk relationships, translate complex product deficiencies into action, and lead your peers by example

What You'll Do (Responsibilities)

• Master Complex Escalations: Act as the final point of contact for high-risk corporate accounts. Step into accounts struggling under standard management to stabilize relationships and restore client confidence.
• Technical Interpretation & Translation: Act as the bridge between engineering and the client. Digest complex technical details, system behavior, and engineering tickets, then articulate status updates and resolutions back to customers clearly.
• Rigorous Project Management: Own cross-functional tracking for major account rollouts, technical overhauls, or complex product issues. Build project trackers and drive internal accountability across departments.
• Strategic Advisory: Manage a slower-ramp, high-touch book of business focused on tier-1 accounts, ensuring deep technical alignment and measurable ROI.
• Change Leadership: Serve as a foundational anchor on the team. Help drive clarity and execution during company reorgs, book reallocations, or operational changes, maintaining an exceptionally high standard for performance.

What You'll Need to Thrive (Requirements)

• 8+ Years of SaaS Account Management: Experience managing a multi-million dollar corporate book ($6.5M+ ARR footprint) with highly complex, enterprise-level accounts.
• Advanced Technical & Analytical Aptitude: High comfort level diving into technical infrastructure, APIs, integrations, or engineering tickets to identify client friction points.
• Elite Crisis Management: A proven track record of successfully de-escalating volatile customer situations at the executive level. You are comfortable being the "last line of defense" for a business relationship.
• Strong Project Management: Exceptional organizational skills with experience tracking multi-variable initiatives across product, engineering, and support teams.
• Executive Presence: Masterful communication skills, with the ability to stand toe-to-toe with C-suite executives and deliver concise, data-backed updates.

What Helps You Stand Out (Nice to Haves)

• Methodical Training: Formal project management certifications (PMP, Agile, Scrum) or specialized technical account management training.
• Restaurant/Tech Expertise: Deep familiarity with POS ecosystems, restaurant tech stack integrations, or hospitality SaaS.