Director of Customer Success & Account Management

DealRoom Inc • Boston, MA

18d • Hybrid

About The Position

We are hiring a Head of Customer Success & Account Management to lead the entire post-sales organization, including:

New customer onboarding
The support function (AI-first strategy)
All post-sales commercial ownership (renewals & expansion)
This leader will transform Customer Success into a modern, commercially accountable, and operationally efficient organization aligned to our bootstrapped model.

Requirements

• 7+ years in B2B SaaS Customer Success / Account Management
• Experience owning NDR/GRR within a meaningful revenue base
• Demonstrated success managing renewals and expansion targets
• Experience implementing scalable support and onboarding systems utilizing AI
• Fluency and comfort in analyzing customer segmentation/tiering to optimize headcount and book of business load as we scale
• Proven ability to build and develop teams
• Commercial operator with revenue forecasting rigor
• Strong analytical skills with deep CRM and CS platform fluency
• Proactive operator who leverages AI and automation
• Experience building playbooks and modern CS operating models
• Ability to balance strategic thinking with hands-on execution
• Executive presence and strong cross-functional partnership skills

Nice To Haves

• Experience operating within a bootstrapped, capital-efficient environment
• Strong partnership with Product organizations
• Track record of building VOC programs
• Experience owning pre-sales/sales engineering, as well as onboarding

Responsibilities

• Build & Develop a High-Performance CS Organization
• Recruit, hire, onboard, and develop top-tier CSMs, Account Managers, and Support professionals
• Establish the “Right People in the Right Seats”, performance metrics, and accountability frameworks to ensure we are delivering the wow for both prospective and current customers
• Create a culture of continuous coaching, mentoring, and performance improvement
• Build internal bench for future talent
• Own and Optimize Post-Sales Commercials
• Develop and implement structured renewal and expansion playbooks
• Track, manage, and forecast all renewal and upsell opportunities with rigor
• Continuously optimize commercial processes to increase GRR and NDR
• Establish clear expansion strategy across segmentation tiers
• Introduce executive alignment motion in strategic accounts
• Ensure predictable renewal forecasting and risk management
• Lead an AI-First Support & Onboarding Strategy
• Redesign onboarding to accelerate time-to-value
• Implement AI-first support motions aligned to our bootstrapped model
• Leverage modern CS tools, automation, and GTM engineering to increase:
• Efficiency
• Productivity
• Adoption
• Usage
• Value realization
• Build scalable, repeatable playbooks across the customer lifecycle
• Improve CSAT through structured feedback loops and proactive engagement
• Optimize the existing infrastructure to increase retention and expansion (the now)
• Modernize Customer Success to proactively drive value realization
• Elevate the experience from reactive support to strategic partnership
• Establish clear health scoring and early risk detection
• Continuously iterate on tools, tech stack, and playbooks
• Act as the Voice of the Customer (the future)
• Establish a strong partnership with Product
• Build structured VOC feedback loops
• Translate customer insights into product influence
• Diagnose and report on reasons for customer churn, creating actionable insights
• Inform roadmap priorities through data, trends, and customer patterns

Benefits

• Wellness: PTO, 100% company paid medical, dental, and vision insurance, FSA options, as well as 401k + matching for our employees
• Invested in your future: Eligible employees enjoy new hire equity and a quarterly bonus structure tied to NDR/GRR performance
• Continuous learning: Curiosity is encouraged and supported
• Feedback culture: Radical candor and performance coaching are core
• International: Collaboration across cross-country teams
• Inclusive: We celebrate diversity across race, gender, age, orientation, religion, disability, and background

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed